PHOTOCHROMIC NAPHTHOPYRAN COMPOUNDS WITH REDUCED TEMPERATURE DEPENDENCE FIEED The present invention relates to fused ring photochromic such as photochromic naphthopyran and photochromic compositions and photochromic articles that include such photochromic BACKGROUND Photochromic compounds undergo a transformation from one state to another state in response to certain wavelengths of electromagnetic radiation Each state has a characteristic absorption For many photochromic compounds transform from an unactivated bleached or substantially state to an activated state upon exposure to actinic When the actinic radiation is the photochromic compounds reversibly transform from the activated state back to the unactivated A reversible photochromic is a photochromic compound that converts from an unactivated state to an activated state in response to actinic and reverts back to the unactivated state in response to thermal The activation reaction unactivated to is primarily photochemical while the deactivation reaction activated to is primarily Such photochromic compounds display what is or dependence dependence is a result of a shift in the equilibrium concentrations between the unactivated state and the activated state due to As the temperature the equilibrium is shifted towards the unactivated As the temperature the equilibrium is shifted towards the activated Articles and materials containing these photochromic compounds therefore will present a different response depending on their Because the forward reaction is light activated and the reverse reaction is thermally thermally reversible photochromic when tend to be darker at colder temperatures and clearer at warmer The temperature dependence effect is a particular problem with photochromic such as photochromic eyewear The coloration of the photochromic article is affected by the temperature at which it is For a photochromic article incorporating a thermally reversible photochromic compound may not get sufficiently dark when the ambient temperature is hot may get too dark when the ambient temperature is is meant the temperature of the environment in immediate contact with the photochromic For for photochromic eyewear lenses worn by a the ambient temperature would be the temperature of the air in immediate contact with the photochromic eyewear Photochromic compounds can be characterized with regard to various such as but not limited fade change in optical density the change in optical density at sensitivity the efficiency at which the photochromic compound absorbs radiation required to activate the photochromic compound and dichroic properties as in the case of which can be quantified with regard to absorption ratio The change in optical density measures the change from the unactivated state to the activated One way to quantify the temperature dependence of photochromic compounds is by measuring the difference in the optical density of the activated state at two When comparing photochromic all else being the compound with the smaller difference in optical density between two temperatures in the activated state is considered to have a smaller temperature a reduced temperature dependence It would be desirable to provide a photochromic compound having a reduced temperature dependence compared to known photochromic For it would be desirable to provide new photochromic naphthopyran compounds with reduced temperature SUMMARY A photochromic compound comprises a core skeletal structure represented by the following Formula Formula wherein D is oxygen or E is or a is 0 or R1 is or substituted or unsubstituted R2 and are each independently selected from substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted and the photochromic compound is a thermally reversible photochromic The features that characterize the present invention are pointed out with particularity in the which are annexed to and form a part of this These and other features of the its operating advantages and the specific objects obtained by its use will be more fully understood from the following detailed description in which non limiting embodiments of the invention are illustrated and BRIEF DESCRIPTION OF THE DRAWINGS 1 illustrates a general Scheme of an exemplary method for preparing photochromic compounds of the 2 illustrates a general Scheme of another exemplary method for preparing photochromic compounds of the DETAILED DESCRIPTION As used the include plural referents unless otherwise expressly and unequivocally limited to one As used the is synonymous Unless otherwise all ranges or ratios disclosed herein are to be understood to encompass any and all subranges or subratios subsumed For a stated range or ratio to should be considered to include any and all subranges between inclusive the minimum value of 1 and the maximum value of that all subranges or subratios beginning with a minimum value of 1 or more and ending with a maximum value of 10 or such as but not limited 1 to to and to As used unless otherwise representations of linking such as divalent linking are inclusive of other appropriate such but not limited For purposes of O the representation of the divalent linking group or equivalently is inclusive of the representation equivalently or Other than in the operating or where otherwise all numbers expressing quantities of reaction and so forth used in the specification and claims are to be understood as modified in all instances by the is meant plus or minus percent of the stated such as plus or minus ten percent of the stated this should not be considered as limiting to any analysis of the values under the doctrine of As used molecular weight values of such as weight average molecular weights and number average molecular weights are determined by gel permeation chromatography using appropriate such as polystyrene As used the means homopolymers prepared from a single monomer copolymers prepared from at least two monomer and graft As used the term and similar such as acid means derivatives of acrylic acid and methacrylic inclusive of acrylate methacrylate acrylic acid and methacrylic As used the means methacrylic acid acrylic The photochromic compounds of the present invention with some also referred to herein as compounds when they include one or more lengthening such as The photochromic compounds of the present as described but not limited photochromic compounds represented by Formula Formula Formula and Formula in each case can optionally further include one or more resulting from the synthesis of such As used the term and similar such as means having an absorption spectrum for at least visible radiation that varies in response to absorption of at least actinic as used herein the means any substance that is adapted to display photochromic properties adapted to have an absorption spectrum for at least visible radiation that varies in response to absorption of at least actinic and which includes at least one photochromic As used the means electromagnetic radiation that is capable of causing a response in a such but not limited transforming a photochromic material from one form or state to another as will be discussed in further detail As used the means capable of absorbing one of two orthogonal plane polarized components of at least transmitted radiation more strongly than the As used the and similar such as means possessing providing both photochromic properties having an absorption spectrum for at least visible radiation that varies in response to at least actinic and dichroic properties capable of absorbing one of two orthogonal plane polarized components of at least transmitted radiation more strongly than the As used and unless stated otherwise or otherwise the term includes thermally reversible photochromic materials and compounds and reversible photochromic materials and The term reversible photochromic as used herein means capable of converting from a first for example to a second for example in response to actinic and reverting back to the first state in response to thermal The reversible photochromic as used herein means capable of converting from a first for example to a second for example a in response to actinic and reverting back to the first state in response to actinic radiation of substantially the same as the of the colored state discontinuing exposure to such actinic As used to modify the the are not intended to refer to any particular order or but instead refer to two different conditions or For purposes of the first state and the second state of a photochromic compound can differ with respect to at least one optical such as but not limited to the absorption of visible UV according to various embodiments disclosed the photochromic compounds of the present invention can have a different absorption spectrum in each of the first and second For while not limiting a photochromic compound of the present invention can be clear in the first state and colored in the second a photochromic compound of the present invention can have a first color in the first state and a second color in the second As used the means pertaining to or associated with light For according to various embodiments disclosed the optical article or element or device can be chosen from ophthalmic elements and display elements and or active and passive liquid crystal cell elements and As used the means pertaining to or associated with the eye and examples of ophthalmic articles or elements include corrective and including single vision or which can be either segmented or lenses but not limited bifocal trifocal lenses and progressive as well as other elements used to or enhance or including without contact magnifying and protective lenses or As used the means the visible or machine representation of information in designs or examples of display elements include and security such as security As used the means an aperture adapted to permit the transmission of radiation there examples of windows include automotive and aircraft and optical As used the means a surface that specularly reflects a large fraction of incident As used the crystal refers to a structure containing a liquid crystal material that is capable of being A example of a liquid crystal cell element is a liquid crystal As used spatial or directional such and the relate to the invention as it is depicted in the drawing It is to be that the invention can assume various alternative orientations such terms are not to be considered as As used the mean or positioned on but not necessarily in direct contact with the underlying or surface of the underlying For a a substrate does not preclude the presence of one or more other or films of the same or different composition located between the positioned or formed layer and the As used recitations relating to ring positions such but not limited or means a particular position in the ring such as the core skeletal of a chemical such as the ring photochromic compounds of the present and which are depicted herein in accordance with some embodiments by numbers within the ring structures of representative chemical formulas such but not limited to Formulas skeletal is meant a compound comprising at least the skeletal structure depicted in the associated The core skeletal structure is provided for purposes of identifying numbered ring it is to be understood unless specifically shown to the the core skeletal can have one or more atoms or one or more groups specifically illustrated on the corresponding bonded to one or more of the numbered ring positions on the core skeletal which can be the same or different from one The photochromic compounds of the present invention are referred to herein with reference to the skeletal which can be represented by one or more such as but not limited to Formulas All documents or portions of such as but not limited to issued patents and patent referred to and unless otherwise are to be considered to by in their As used recitations means a group but not limited alkyl heterocycloalkyl aryl heteroaryl in which at least one hydrogen thereof has been replaced or substituted with a group that is other than such but not limited alkoxy halo groups and hydroxyl thiol alkylthio ketone aldehyde ester carboxylic acid phosphoric acid phosphoric acid ester sulfonic acid sulfonic acid ester nitro cyano alkyl groups aralkyl alkenyl alkynyl haloalkyl perhaloalkyl heterocycloalkyl aryl groups alkaryl including hydroxyl substituted such as and including heteroaryl groups heteroaryl amine such as where Ri and are each independently for from or carboxylate siloxane alkoxysilane polysiloxane amide carbamate carbonate urea polyester polyether polycarbonate polyurethane acrylate methacrylate or combinations including those classes and examples as described further refers to an aromatic cyclic monovalent hydrocarbon and the refers to a cyclically conjugated hydrocarbon with a stability to that is significantly greater than that of a hypothetical localized Examples of aryl groups include aryl such but not limited and As used recitations and related terms but not limited haloalkyl haloalkenyl haloalkynyl haloaryl groups and means a group in which at least and up to and including all of the available hydrogen groups thereof is substituted with a halo The is inclusive of As used the term substituted group and related terms but not limited perhaloalkyl perhaloalkenyl perhaloalkynyl perhaloaryl groups or means a group in which all of the available hydrogen groups thereof are substituted with a halo For perhalomethyl is perhalophenyl is where X represents one or more halo such but not limited to Cl or As used recitations or such as linear or branched are herein understood to a methylene group or a methyl groups that are linear such as linear alkyl and groups that are appropriately such as branched alkyl The as used means linear or cyclic or acyclic Finear or branched alkyl can include such as such as such as such as C 1 Examples of alkyl groups from which the various alkyl groups of the present invention can be selected but are not limited those recited further Alkyl groups can The as used means groups that are appropriately such but not limited cycloalkyl but not limited cyclic or cyclic Examples of cycloalkyl groups but are not limited those recited further The as used also bridged ring polycycloalkyl groups bridged ring polycyclic alkyl such but not limited and and fused ring polycycloalkyl groups fused ring polycyclic alkyl such but not limited and The term as used means groups that are appropriately such but not limited heterocycloalkyl such as C7 heterocycloalkyl such as heterocycloalkyl and which have at least one hetero atom in the cyclic such but not limited and combinations Examples of heterocycloalkyl groups but are not limited tetrahydropyranyl and The as used also bridged ring polycyclic heterocycloalkyl such but not limited and fused ring polycyclic heterocycloalkyl such but not limited and The term as used but is not limited such but not limited heteroaryl fused ring polycyclic heteroaryl and means an aryl group having at least one hetero atom in the aromatic or in at least one aromatic ring in the case of a fused ring polycyclic heteroaryl Examples of heteroaryl groups but are not limited and As used the ring and similar terms such fused ring fused ring and fused ring group means a fused ring polycyclic group that includes at least one aryl ring and at least one cycloalkyl ring that are fused together to form a fused ring For purposes of examples of fused ring groups but are not limited to and The as used includes but is not limited to such but not limited and means an alkyl group substituted with an aryl Examples of aralkyl groups but are not limited benzyl and Representative alkyl groups but are not limited nonyl and Representative alkenyl groups but are not limited allyl and Representative alkynyl groups but are not limited and Representative cycloalkyl groups but are not limited and cyclooctyl Representative heterocycloalkyl groups but are not limited tetrahydropyranyl and Representative aryl groups but are not limited and tetracenyl structural isomers Representative heteroaryl groups but are not limited and Representative aralkyl groups but are not limited benzyl and The as used but is not limited a ring wherein the ring is bonded through a ring Examples of heterocycles but are not limited cyclic such as and and such as and As used least one is synonymous or more whether the elements are listed conjuctively or For the least one of and least one of or each mean any one of or or any combination of any two or more of or For A or B or C or A and or A and or B and or all of and As used are synonymous least one whether the elements are listed conjunctively or For the from and from or each mean any one of or or any combination of any two or more of or For A or B or C or A and or A and or B and or all of and The discussion of the invention may describe certain features as being or within certain limitations more within certain It is to be understood that the invention is not limited to these particular or preferred limitations but encompasses the entire scope of the The invention consists or consists essentially the following aspects of the in any The photochromic compounds according to the present invention can be represented by one or more of the core skeletal structures described Each available numbered ring position of the core skeletal structure of Formula can have covalently bonded thereto hydrogen or a group other than for such as a group described Examples of such groups are described With reference to Formula D is oxygen or E is or a is 0 or 1 R1 is or substituted or unsubstituted and R2 and are each independently selected from substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted provided that when R2 is a substituted aryl or substituted the substituent does not comprise an aromatic group or a cyclic and provided that when E is oxygen or R2 is not Examples of alkyl groups from which R1 can be selected but are not limited substituted or unsubstituted For R1 can be selected from hydrogen or Examples of alkyl groups from which R2 and can be selected from but are not limited substituted or unsubstituted For R2 and R2 can be selected from methoxyphenyl and haloalkyl perhaloalkyl substituted phenyl and amino alkyl or Each alkyl each heterocycloalkyl each aryl and each heteroaryl substituent herein can in each case be independently selected from one or more of carboxylic polyester polyether polycarbonate polyurethane an acrylate a methacrylate aryl diphenyl alkyl dimethyl cyclic or or or combinations or any other group as long as it does not adversely impact upon the performance properties of the the photochromic performance properties of the Each amino substituent can be a or tertiary Additionally or the photochromic compounds of the present invention can be represented by the core skeletal structure of Formula With reference to Formula and R2 are as previously described with respect to Formula As described the remaining numbered ring positions of the core skeletal structure of Formula without a specifically shown substituent can have covalently bonded thereto hydrogen or a group other than for such as a group described With further reference to Formula R3 and R4 are each independently selected from substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted carboxylic or a group comprising polyurethane or combinations or R3 and R4 together form an aliphatic ring having 3 to 20 ring member carbon a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above aliphatic a hetero ring having 3 to 20 ring member or a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above hetero together with the 13 carbon atom bonded For R3 and R4 together may form a spiro substituent selected from a substituted or unsubstituted a substituted or unsubstituted heterocyclic the ring and ring being annellated with 1 or 2 aryl each substituent independently being For R3 and R4 can be each independently selected from substituted or unsubstituted alkyl or substituted or unsubstituted For R3 and R4 can be selected from dimethyl or With further reference to Formula each alkyl each heterocycloalkyl each aryl and each heteroaryl substituent can be in each case independently selected from one or more of the substituents described Additionally or the photochromic compounds of the present invention can be represented by the core skeletal structure of Formula With reference to Formula R2 and R4 are as previously described with respect to Formulas As described the remaining numbered ring positions of the core skeletal structure of Formula without a specifically shown substituent can have covalently bonded thereto hydrogen or a group other than for such as a group described With further reference to Formula B and are each independently selected from substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted or B and together form an aliphatic ring having 3 to 20 ring member carbon a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above aliphatic a hetero ring having 3 to 20 ring member or a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above hetero together with the carbon atom bonded For B and together may form a spiro substituent selected from a substituted or unsubstituted a substituted or unsubstituted the ring and heterocyclic ring being annellated with 1 or 2 aryl each substituent independently being For B and can be each independently selected from substituted or unsubstituted With further reference to Formula each aryl substituent and each heteroaryl substituent can be each independently selected from one or more of the substituents described For B and can be each independently selected from substituted or unsubstituted phenyl substituted with and and halo and morpholino Additionally or the photochromic compounds of the present invention can be represented by the core skeletal structure of Formula With reference to Formula R2 and are as previously described with respect to Formulas As described the remaining numbered ring positions 1 and of the core skeletal structure of Formula without a specifically shown substituent can have covalently bonded thereto hydrogen or a group other than for such as a group described With further reference to Formula m is 0 to n is 0 to R5 independently for each and R6 independently for each are each independently selected from a lengthening group halogen selected from or substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted boronic ester or boronic or substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted carboxylic or For R5 independently for each m and R6 independently for each can be each independently selected from substituted or unsubstituted aryl diphenyl alkyl dimethyl cyclic or or For the alkoxy can be a For the haloalkyl can be a For the perhaloalkyl can be a With further reference to Formula each lengthening group L1 can be independently represented by the following Formula Formula and Q3 for each are independently a divalent group selected from the group consisting of unsubstituted substituted unsubstituted substituted unsubstituted substituted unsubstituted or substituted wherein the aryl heteroaryl cycloalkyl and heterocycloalkyl substituents are each independently selected from the group consisting of liquid crystal or and f are each independently chosen from an integer of 1 to and each and S5 is independently chosen for each occurrence from a spacer unit selected from the group consisting substituted substituted and wherein g for each occurrence is independently chosen from an integer from 1 to h for each occurrence is independently chosen from an integer from 1 to and the substituents for the alkylene and haloalkylene are independently selected from the group consisting of alkyl or and a single wherein Z for each occurrence is independently selected from the group consisting of alkyl or and for each occurrence is independently selected from the group consisting of alkyl or or and or branched alkylene the alkylene residue being by cyano or or substituted by provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each P is and and f are each independently chosen from 1 and provided that the sum of f is at least For R6 can be a lengthening group L1 at the With further reference to Formula each alkyl each aryl each heterocycloalkyl and each heteroaryl can be in each case independently selected from one or more of the substituents described R5 can be a halo group at the a fluoro or R5 can be an alkoxy group at the R6 can be a group at the or R6 can be or alkylthio at the 11 As used the such as with regard to substituents of various groups of the photochromic compounds of the present includes a material represented by the following Formula R32 R34 R33 With reference to Formula subscript F is from 2 to such as from 2 to or 2 to or from 2 to or from 2 to or from 2 to or from 2 to in each case inclusive of the recited With further reference to Formula R32 and for each are each independently selected from alkyl or and R34 is selected from or With some R32 and R33 for each are each independently selected from or and R34 is selected from or As used the such as with regard to substituents of various groups of the photochromic compounds of the present alternatively to or in addition to a material represented by Formula includes a material represented by the following Formula With reference to Formula subscript is and subscript is provided that is and subscript is and subscript is provided that is With further reference to Formula R35 independently for each R36 independently for each and each and each R37 independently for each and each are in each case independently selected from alkyl but not limited methyl or or aryl but not limited With some the photochromic compounds of the present such as those described with reference to Formulas can each be used or in combination with one or more other photochromic For the photochromic compounds of the present invention can be used in conjunction with one or more other photochromic compounds having activated absorption maxima within the range of 300 to the photochromic compounds according to the present invention can be used in conjunction with one or more complementary conventional polymerizable or compatiblized photochromic such as for those disclosed in Patent line 39 to line and line 65 to line The photochromic compounds of the present invention can be used in combination with a mixture of other photochromic For although not limiting mixtures of photochromic compounds can be used to attain certain activated such as a near neutral gray or near neutral for Patent line 66 to line which describes the parameters that define neutral gray and brown Examples of classes of other photochromic compounds that can be used in combination with the photochromic compounds of the present but are not limited spiro thermally reversible photochromic and reversible photochromic and mixtures Further examples of other photochromic compounds that can be used in combination with the photochromic compounds of the present invention but are not limited those disclosed at column line 20 through column line 13 of US Photochromic compounds according to the present invention can be prepared in accordance with For purposes of illustration and with reference to 1 and general synthetic Schemes 1 and for the preparation of photochromic compounds according to the present invention is described as Further detailed descriptions of the preparation of photochromic compounds of the present invention are provided further herein in the In 1 and the various such as R2 and and related such as m and of the various compounds are each as described previously represent precursors of such 1 illustrates a cross coupling reaction catalyzed with various palladium source and ligand combinations to convert aryl or tosylates to an amide For see the publication et 2 illustrates that an group can be made by converting the bromide group to a amine group using palladium cross coupling conditions followed by hydrolysis to the amino group with For example see the publication et The conversion from the group to the carbamate can be accomplished by reacting the with dialkyl For example see et The conversion of the group to the group can be accomplished by reaction of the with a substituted isocyanate This reaction can be catalyzed by typical urethane such as dibutyltin dilaurate or trialkyl In accordance with the present invention there is also provided a photochromic which includes at least one photochromic compound according to the present such as those represented by Formula or as described previously The photochromic composition can an organic in which the organic material is at least one of a polymeric an oligomeric or a monomeric and a photochromic compound according to the present which is incorporated into at least a portion of the organic The photochromic compound can be incorporated into a portion of the organic material by methods but not limited at least one of blending or bonding the photochromic compound with the organic material or a precursor of the organic As used herein with reference to the incorporation of photochromic compounds into an organic the and mean that the photochromic is intermixed or intermingled with the at least a portion of the organic but not bonded to the organic as used herein with reference to the incorporation of photochromic compounds into an organic the mean that the photochromic is such as by one or more covalent to a portion of the organic material or a precursor For although not limiting the photochromic material can be linked to the organic material through a reactive When the organic material is a polymeric the photochromic compound can be incorporated into at least a portion of the polymeric material or at least a portion of the monomeric material or oligomeric material from which the polymeric material is For photochromic according to the present invention that have a reactive substituent can be bonded to an organic material such as a or polymer having a group with which a reactive moiety may be or the reactive moiety can be reacted as a in the polymerization reaction from which the organic material is for in a As discussed the photochromic compositions according to present invention can include an organic material chosen from a polymeric an oligomeric material a monomeric with some Examples of polymeric materials that can be used with the photochromic compositions of the present invention but are not limited copolymers of ethylene and vinyl copolymers of ethylene and vinyl copolymers of vinyl and vinyl alcohol as those that result from the partial saponification of copolymers of ethylene and vinyl cellulose acetate aminoplast functional functional and combinations and mixtures Further classes and examples of polymeric materials that can be used with the photochromic compositions of the present invention but are not limited those disclosed at column line 45 through column line 67 of US The photochromic composition of the present invention can include at least one a complementary photochromic material one or more of those other photochromic materials and compounds described previously a a thermal a polymerization a a light a heat a mold release a rheology control a leveling a free radical an adhesion The photochromic composition according to the present invention can be a photochromic coating Photochromic coating compositions of the present invention can a photochromic compound according to the present such as described previously herein with regard to Formula or a resin composition that is optionally and optionally a The photochromic coating composition can be in the form of liquid coatings and powder The photochromic coating compositions of the present invention can be thermoplastic or thermosetting coating The photochromic coating composition can be a curable or thermosetting coating The curable resin composition of the curable photochromic coating compositions according to the present invention can a first reactant having functional an epoxide functional polymer and a second reactant that is a crosslinking agent having functional groups that are reactive towards and that can form covalent bonds with the functional groups of the first The first and second reactants of the curable resin composition of the curable photochromic coating composition can each independently include one or more functional and are each present in amounts sufficient to provide cured photochromic coatings having a desirable combination of physical optical solvent and Examples of curable resin compositions that can be used with the curable photochromic coating compositions according to the present invention but are not limited curable resin compositions including epoxide functional polymer polymers containing residues of glycidyl and epoxide reactive crosslinking agent containing active such as thiols and and curable resin compositions including active hydrogen functional polymer amine functional and capped isocyanate functional crosslinking isocyanate functional crosslinking is meant a crosslinking agent having two or more capped isocyanate groups that can decap under cure conditions at elevated to form free isocyanate groups and free capping The free isocyanate groups formed by decapping of the crosslinking agent are preferably capable of reacting and forming substantially permanent covalent bonds with the active hydrogen groups of the active hydrogen functional polymer with the hydroxy groups of a hydroxy functional Further examples of curable resin compositions that can be used with the curable photochromic coating compositions according to the present invention but are not limited those disclosed paragraphs through of WO and paragraphs through through and through of WO Curable photochromic coating compositions according to the present invention contain additives such as waxes for flow and flow control adjuvant resin to modify and optimize coating antioxidants and ultraviolet light Examples of useful antioxidants and UV light absorbers include those available commercially from BASF under the trademarks IRGANOX and These optional when are typically present in amounts up to 20 percent by weight from to 10 percent by based on total weight of resin solids of the curable resin Photochromic photochromic articles and photochromic coating compositions according to the present invention can further include additives that aid or assist in the processing performance of the compositions or limiting examples of such additives include thermal polymerization light stabilizers but not limited ultraviolet light absorbers and light such as hindered amine light stabilizers heat mold release rheology control leveling agents but not limited free radical adhesion promoters as hexanediol diacrylate and coupling and combinations and mixtures The photochromic compounds of the present invention can be used in amounts such that the organic material or substrate photochromic articles and photochromic into which the photochromic compounds are incorporated or otherwise connected exhibits desired optical The amount and types of photochromic material can be selected such that the organic material or substrate is clear or colorless when the photochromic compound is in the in the bleached or unactivated and can exhibit a desired resultant color when the photochromic compound as a photochromic naphthopyran of the present is in the when activated by actinic The precise amount of the photochromic material that is utilized in the various photochromic compositions and articles described herein is not critical provided that a sufficient amount is used to produce the desired The particular amount of the photochromic material used can depend on a variety of such as but not limited the absorption characteristics of the photochromic the color and intensity of the color desired upon and the method used to incorporate or connect the photochromic material to the Photochromic compositions according to the present invention can include the photochromic compound according to the present including the compounds represented by Formula or in an amount of from to 40 weight such as from to 15 weight such as from to 5 weight based on the weight of the photochromic For purposes of further the amount of the photochromic including the compounds represented by Formula or that is incorporated into an organic material can range from to 40 weight such as from to 15 weight such as from to 5 weight based on the weight of the organic The present invention also relates to photochromic articles that include one or more photochromic compounds according to the present such as represented by Formula or The photochromic articles can be prepared by such as by imbibition coating coating and lamination For the photochromic articles can be selected from ophthalmic display active liquid crystal cell and passive liquid crystal cell For the photochromic articles of the present invention can be ophthalmic and the ophthalmic articles can be selected from corrective non corrective contact magnifying protective and For the photochromic articles of the present invention can be display and the display articles can be selected from and security The present invention is more particularly described in the following which are intended as illustrative since numerous modifications and variations therein will be apparent to those skilled in the EXAMPLES The following examples are provided to illustrate photochromic compounds of the particularly the improvement in temperature dependence of photochromic compounds of the Part 1 provides descriptions of the synthesis of photochromic compounds of the Part 2 provides an evaluation of the photochromic performance of the photochromic compounds of the invention versus comparative photochromic Part Synthesis of photochromic compounds Example 1 Step was added to a round bottom flask containing 100 mL of CH2CI2 with followed by addition of acid A solution of g in 25 mL was slowly added to the reaction mixture and heated to After three additional g in 10 mL was After an additional hour at the solution was cooled to room and was passed through a silica plug using CH2CI2 as then concentrated under Crystallization from ethyl gave an yield of 11 13 1 as confirmed by 1 Step The product of step 1 above and benzamide were added under N2 atmosphere into a round bottom flask containing 100 mL toluene and ethanol To this was added CS2CO3 and dimethylxanthene with The solution was sparged with nitrogen for 10 was added and the mixture was heated to After two hours of reflux the reaction mixture was cooled to room temperature then added to The pH was adjusted to pH 7 using concentrated followed by extraction with ethyl acetate The organic layer was dissolved in 50 mL CH2CI2 and dried over anhydrous The solution was passed through a short silica plug using EtO as The desired fraction was and precipitated from methanol to give a product with the structure shown in Table Additional photochromic dyes were prepared according to the procedure for Example For each an appropriately substituted was used in place of in Step as indicated in Table 1 to give the desired substitution pattern in the final the of Step 1 was replaced with an equimolar amount of the disubstituted indicated in the column according to Table the benzamide of Example Step was replaced with an equimolar amount of the amide indicated in column according to Table Examples Example 24 Step diol was added to a round bottom flask containing 200 mL of CH2CI2 under nitrogen and warmed to until fully acid was then A solution of in 25 mL CH2CI2 was added slowly to the reaction mixture at 40 with then heated at reflux The reaction mixture was washed with aqueous NaHC03 solution and dried over anhydrous After removal of solvent under the residue was combined with a minimal volume of CH2CI2 and then passed through a silica gel plug with CH2CI2 Then solvent was removed and the product was crystallized from diethyl The product was characterized by 1 NMR as 1 Yield was Step The product of Step 1 above was dissolved in 150 mL of CH2CI2 followed by addition of triethylamine was added with Trifluoromethanesulfonic anhydride was added dropwise with stirring under nitrogen at ice cold Once the addition was complete the reaction was brought to room temperature and stirred for one The solution was concentrated and passed through a silica gel Solvent was removed and the residue was washed with The product was characterized by 1 NMR as 13 13 1 Yield was Step The product of step 2 above and benzamide were added under nitrogen into a round bottom flask containing 50 mL toluene and EtOH with a magnetic Then CS2CO3 and Xanthphos were added with The solution was sparged with nitrogen for 10 minutes followed by addition of then heating to After 2 hours at the reaction was cooled to room temperature then added to The pH was adjusted to less than 7 using concentrated The mixture was extracted with and the organic layer concentration by The residual mass was dissolved in 50 mL of dried over anhydrous and passed through a short silica gel plug using EtO as The desired fraction was and the product was precipitated from methanol to yield solid product with the structure shown in Table Additional photochromic dyes were prepared according to the procedure for Example For each an appropriately substituted was used in place of in Step 1 as indicated in Table 1 to give the desired substitution pattern in the final the of Step 1 was replaced with an equimolar amount of the 1 1 stituted 1 indicated in column according to Table the benzamide of Example Step was replaced with an equimolar amount of the amide indicated in column according to Table Example 27 The product of Example 24 was dissolved in 25 mL tetrahydrofuran under nitrogen then immersed into an To this was added M in and the mixture stirred for 10 after which methyl iodide was The reaction mixture was removed from the ice bath and stirred for an hour at room temperature then poured into adjusted to pH 7 with dilute HC1 then extracted with Solvent was removed and the residue was run through a silica gel plug using Hexanes and EtOAc over 30 The product was confirmed by NMR as having a structure consistent with the amide shown in Table Example 28 The procedure of Example 27 was followed using the product of Example 23 in place of the product of Example Example 29 Step 2 was added to a round bottom flask containing 100 mL toluene under a nitrogen blanket at room The solution was sparged with nitrogen for five then 1M lithium amide in THF and were added followed by 1M in Toluene After thirty minutes at room the reaction mixture was poured into water followed by addition of saturated ammonium chloride with vigorous The solution was extracted with ethyl acetate and the organic layer dried over anhydrous and solvent removed by The residue was passed through a Rf column available from Teledyne with EtO as the The desired fraction was concentrated and recrystallized from hexanes and methanol to give 11 13 Yield was Step The product of Step 1 above was added to a 20 mL vial containing Dimethyl Carbonate and Potassium with Using a hot the reaction was heated to boiling for eight minutes and then the vial was removed from the heat After extraction with ethyl the solution was dried over anhydrous and solvent removed by The residue was passed through a Rf column available from Teledyne with EtO as the The product was recrystallized from hexanes and methanol to give the corresponding carbamate product shown in Table Example 30 The procedure of Example 29 was followed using in place of to yield the corresponding carbamate shown in Table Example 31 The product of Step Example 29 was added to a reaction flask containing 10 mL of dichloromethane and Hexyl isocyanate with stirring followed by addition of one diluted drop of tributyl tin The solution was stirred for ten minutes at room temperature at which time a precipitate formed in the This precipitate was collected and identified as the corresponding urea shown in Table The final products of Examples are summarized in Table with the yield of the final step and characterization Table Summary of Examples 1 Yield reported corresponds to the step creating the bond at the position Part Results Each of the photochromic dyes from Examples 1 through 14 and 24 through and each comparative example shown in Table 4 were incorporated into a polyurethane coating system as described in US examples at the same mol and applied at the same coating All samples were cured at for 1 The temperature dependence of the samples was determined by measuring the change in the optical density from the bleached to the darkened state at two and using methods described Prior to testing for temperature each of the coated lenses was conditioned by first being exposed to ultraviolet light for 10 minutes at a distance of about 14 centimeters to activate the photochromic The UVA to 380 irradiance at the lens was measured with a Model spectroradiometer and found to be watts per square The lens was then placed under a 500 high intensity halogen lamp for 10 minutes at a distance of about 36 centimeters to bleach the photochromic The illuminance at the lens was measured with the spectroradiometer and found to be The were then kept in a dark environment at room temperature 70 to or 21 to for at least 1 hour prior to testing on an optical Prior to optical bench the lenses were measured for ultraviolet absorbance at 390 The BMP optical bench was fitted with two Model Xenon arc lamps at right angles to each The light path from Lamp 1 was directed through a 3 mm filter and appropriate neutral density filters that contributed to the required UV and partial visible light irradiance The light path from Lamp 2 was directed through a 3 mm a short band 400 nm cutoff filter and appropriate neutral density filters in order to provide supplemental visible light A 2 inch x 2 inch polka dot beam at to each lamp is used to mix the two The combination of neutral density filters and voltage control of the Xenon arc lamp were used to adjust the intensity of the Proprietary software BMPSoft version was used on the BMP to control air cell and sample filter selection and response A Model MCS with fiber optic cables for light delivery through the lens was used for response and color Photopic response measurements were collected on each The power output of the optical the dosage of light that the lens was exposed was adjusted to Watts per square meter integrated from nm and 50 Klux integrated from Measurement of this power setpoint was made using an irradiance probe and the calibrated Zeiss The lens sample cell was fitted with a quartz window and sample The temperature in the sample cell was controlled at C and C through the software with a modified Model environment Measurement of the dynamic photochromic response and color measurements was made using the same Zeiss with fiber optic cables for light delivery from a tungsten halogen lamp and through the The collimated monitoring light beam from the fiber optic cable was maintained perpendicular to the test sample while passing through the sample and directed into a receiving fiber optic cable assembly attached to the The exact point of placement of the sample in the sample cell was where the activating xenon arc beam and the monitoring light beam intersected to form two concentric circles of The angle of incidence of the xenon arc beam at the sample placement point was from Response in terms of a change in optical density from the unactivated or bleached state to the activated or colored state were determined by establishing the initial unactivated opening the shutter from the Xenon and measuring the transmittance through activation at selected intervals of Change in optical density at a prescribed temperature was determined according to the where Tb is the percent transmittance in the bleached Ta is the percent transmittance in the activated state both measured at that Optical density measurements were based on photopic optical The temperature dependence of the samples was determined using the changes in optical density at both 10 and 35 The measure was calculated as the percent loss of the photopic response between the two DOϋ loss The activation time was 15 minutes at 35 and 30 minutes at 10 Results are reported in Table 4 as DOϋ The lower the DOϋ the better the temperature Table 4 shows the temperature dependence of selected examples versus comparative grouped according to further Structures for the examples are found in Table Table 4 The results shown in Table 4 clearly demonstrate the improvement in temperature dependence provided by the presence of an carbamate or urea in the position when compared directly with analogous compounds having either a hydrogen or methoxy group in the same The present invention can further be characterized by one or more of the following Clause An indenofused naphthopyran having the core skeletal structure represented by Formula Formula D is oxygen or E is or a is 0 or 1 R1 is or substituted or unsubstituted R2 and are each independently selected from substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted provided that when R2 is a substituted aryl or substituted the substituent does not comprise an aromatic group or a cyclic and provided that when E is oxygen or R2 is not Clause The indeno fused naphthopyran of clause R1 is hydrogen or and R2 is or substituted or unsubstituted Clause The indeno fused naphthopyran of clauses 1 or having the skeletal structure represented by Formula Formula R3 and R4 are each independently selected from substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted carboxylic or a group comprising a a polyurethane or combinations or R3 and R4 together form a spiro substituent selected from a substituted or unsubstituted ring containing 3 to 10 carbon a substituted or unsubstituted ring containing 1 or 2 oxygen atoms and 3 to 10 carbon atoms including the spirocarbon the ring and heterocyclic ring being annellated with 1 or 2 benzene each substituent independently being Clause The indeno fused naphthopyran of clause wherein R3 and R4 are each independently selected from substituted or unsubstituted Clause The indeno fused naphthopyran of clauses 3 or having the core skeletal structure represented by Formula Formula B and are each independently selected from substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted or B and taken together form a ring Clause The indenofused naphthopyran of clause wherein B and are each independently selected from substituted or unsubstituted Clause The indenofused naphthopyran of clause wherein B and are each independently selected from substituted or unsubstituted halo or morpholino Clause The indenofused naphthopyran of any of clauses 5 to having the core skeletal structure represented by Formula Formula m is 0 to and n is 0 to and R5 independently for each and R6 independently for each are each independently selected acrylate or amino or a lengthening group halogen selected from or substituted or unsubstituted boronic ester or boronic or substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or carboxylic or Clause The indeno fused naphthopyran of clause wherein wherein R5 independently for each m and R6 independently for each are each independently selected from or substituted or unsubstituted Clause The indenofused naphthopyran of clause wherein each lengthening group L1 is independently represented by the following Formula Formula III k and Q3 for each are independently a divalent group selected from the group consisting of unsubstituted substituted unsubstituted substituted unsubstituted substituted unsubstituted or substituted wherein the aryl heteroaryl cycloalkyl and heterocycloalkyl substituents are each independently selected from the group consisting of liquid crystal or and f are each independently chosen from an integer of 1 to and each and Ss is independently chosen for each occurrence from a spacer unit selected from the group consisting substituted substituted or wherein g for each occurrence is independently chosen from an integer from 1 to h for each occurrence is independently chosen from an integer from 1 to and the substituents for the alkylene and haloalkylene are independently selected from the group consisting of alkyl and and a single wherein Z for each occurrence is independently selected from the group consisting of or and for each occurrence is independently selected from the group consisting of alkyl or or and or branched alkylene the alkylene residue being by cyano or or substituted by provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each P is and and are each independently chosen from 1 and provided that the sum of f is at least Clause The indeno fused naphthopyran of any of clauses 1 to wherein each alkyl each heterocycloalkyl each aryl or each heteroaryl is in each case independently selected from carboxylic polyester polyether polycarbonate polyurethane an acrylate a methacrylate or combinations Clause The indeno fused naphthopyran of clause wherein each alkyl each heterocycloalkyl each aryl or each heteroaryl substituent can be further substituted with monoalkyl substituted monoalkoxy substituted an acrylate a methacrylate or combinations A photochromic composition comprising the indeno fused naphthopyran of any of clauses 1 to Clause A photochromic article comprising the indenofused naphthopyran ofany of clauses 1 to wherein the photochromic article is selected from ophthalmic display active liquid crystal cell or passive liquid crystal cell Clause The photochromic article of clause wherein the photochromic article is selected from ophthalmic and the ophthalmic articles are selected from corrective contact magnifying protective or Clause The photochromic article of clause wherein the photochromic article is selected from display and the display articles are selected from or security Clause An represented by Formula Formula D is oxygen or E is or a is 0 or 1 R1 is or substituted or unsubstituted R2 and are each independently selected from substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted provided that when R2 is a substituted aryl or substituted the substituent does not comprise an aromatic group or a cyclic provided that when E is oxygen or R2 is not m is 0 to n is 0 to and and are independently selected from hydrogen or a group other than Clause The naphthopyran of clause R1 is hydrogen or unsubstituted and R2 is substituted or unsubstituted or substituted or unsubstituted Clause The naphthopyran of clauses 17 or R3 and R4 are each independently selected from substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted carboxylic or a group comprising polyurethane or combinations or R3 and R4 together form an aliphatic ring having 3 to 20 ring member carbon a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above aliphatic a hetero ring having 3 to 20 ring member or a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above hetero together with the carbon atom bonded Clause The naphthopyran of any of clauses 17 to wherein R3 and are each independently selected from substituted or unsubstituted Clause The naphthopyran of any of clauses 17 to B and are each independently selected from substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted or B and taken together form a spiro substituent selected from a substituted or unsubstituted a substituted or unsubstituted the ring or ring being annellated with 1 or 2 aryl each substituent independently being Clause The naphthopyran of any of clauses 17 to 21 wherein B and are each independently selected from substituted or unsubstituted Clause The naphthopyran of clauses 21 or wherein each aryl substituent is in each case independently selected from aryl alkyl cyclic or combinations Clause The naphthopyran of any of clauses 21 to wherein B and are each independently selected from substituted or unsubstituted halo or morpholino Clause The naphthopyran of any of clauses 17 to m is 0 to and n is 0 to R5 independently for each and R6 independently for each are each independently selected amino or a lengthening group halogen selected from or substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted boronic ester or boronic or substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted or substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted substituted or unsubstituted carboxylic or Clause The naphthopyran of clause wherein R6 is at the and is a lengthening group Clause The naphthopyran of clauses 25 or wherein R5 independently for each m and R6 independently for each are each independently selected from or substituted or unsubstituted Clause The naphthopyran of any of clauses 25 to wherein each lengthening group L1 is independently represented by the following Formula Formula and Q3 for each are independently a divalent group selected from the group consisting of unsubstituted substituted unsubstituted substituted unsubstituted substituted unsubstituted or substituted wherein the aryl heteroaryl cycloalkyl and heterocycloalkyl substituents are each independently selected from the group consisting of liquid crystal or and f are each independently chosen from an integer of 1 to and each and is independently chosen for each occurrence from a spacer unit selected from the group consisting substituted substituted or wherein g for each occurrence is independently chosen from an integer from 1 to h for each occurrence is independently chosen from an integer from 1 to and the substituentsfor the alkylene and haloalkylene are independently selected from the group consisting of alkyl or and a single wherein Z for each occurrence is independently selected from the group consisting of alkyl or and for each occurrence is independently selected from the group consisting of alkyl or and and or branched alkylene the alkylene residue being by cyano or or substituted by provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each P is and and are each independently chosen from 1 and provided that the sum of f is at least Clause The naphthopyran of any of clauses 17 to wherein each alkyl each aryl each heterocycloalkyl and each heteroaryl is in each case independently selected from carboxylic polyester polyether polycarbonate polyurethane an acrylate a methacrylate or combinations Clause The naphthopyran of clause wherein each alkyl each aryl each heterocycloalkyl or each heteroaryl is in each case independently further substituted with an acrylate group or a methacrylate Clause The naphthopyran of any of clauses 1 to wherein the formula comprises at least one additional identical or located on at least one available position on the core skeletal structure among positions 1 to 13 depicted Clause The naphthopyran of clause wherein said at least one additional substituent is independently selected from alkyl heterocycloalkyl aryl heteroaryl thiol alkylthio ketone aldehyde ester carboxylic acid phosphoric acid phosphoric acid ester sulfonic acid sulfonic acid ester nitro cyano alkyl aralkyl alkenyl alkynyl haloalkyl perhaloalkyl heterocycloalkyl aryl alkaryl hydroxyl substituted aryl alkoxy substituted aryl heterocycloalkyl substituted aryl halo substituted aryl aryl heteroaryl heteroaryl amine carboxylate siloxane alkoxysilane polysiloxane amide carbamate carbonate urea polyester polyether polycarbonate polyurethane acrylate methacrylate aryl amino cyclic amino heteroaromatic or combinations Clause A photochromic composition comprising the naphthopyran of any of clauses 17 to Clause A photochromic article comprising the naphthopyran of any of clauses 17 to wherein the photochromic article is selected from ophthalmic display active liquid crystal cell or passive liquid crystal cell Clause The photochromic article of clause wherein the photochromic article is selected from ophthalmic and the ophthalmic articles are selected from corrective contact magnifying protective or Clause The photochromic article of clause 35 wherein the photochromic article is selected from display and the display articles are selected from or security The present invention has been described with reference to specific details of particular embodiments It is not intended that such details be regarded as limitations upon the scope of the invention except insofar as to the extent that they are included in the accompanying insufficientOCRQuality

WHAT IS CLAIMED IS:

1. An indeno-fused naphthopyran comprising a core skeletal structure represented by Formula (I):

Formula (I)

wherein,

D is oxygen or sulfur;

E is oxygen, sulfur, or NR2’;

a is 0 or 1 ;

R1 is hydrogen, or substituted or unsubstituted alkyl;

R2 and R2’ are each independently selected from hydrogen, substituted or

unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heterocycloalkyl;

provided that when R2 is a substituted aryl or substituted heteroaryl, the substituent does not comprise an aromatic group or a cyclic group; and

provided that when E is oxygen or sulfur, R2 is not hydrogen.

2. The indeno-fused naphthopyran of claim 1, wherein,

R1 is hydrogen or unsubstituted alkyl, and

R2 is substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

3. The indeno-fused naphthopyran of claims 1 or 2, having the core skeletal structure represented by Formula (la):

Formula (la)

wherein, R3 and R4 are each independently selected from

(i) hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heterocycloalkyl, allyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;

(ii) alkoxy, hydroxyl, alkylthio, ketone, aldehyde, ester, carboxylic acid, carboxylate, siloxane, alkoxysilane, or polysiloxane;

(iii) a group comprising polyester, polyether, polycarbonate, polyurethane or combinations thereof; or

(iv) R3 and R4 together form an aliphatic ring having 3 to 20 ring member carbon atoms, a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above aliphatic ring, a hetero ring having 3 to 20 ring member atoms, or a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above hetero ring, together with the 13-position carbon atom bonded thereto.

4. The indeno-fused naphthopyran of claim 3, wherein R3 and R4, are each

independently selected from substituted or unsubstituted alkyl.

5. The indeno-fused naphthopyran of claims 3 or 4, comprising the core skeletal structure represented by Formula (lb):

Formula (lb)

wherein,

B and B’ are each independently selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, or substituted or unsubstituted alkynyl, or B and B’ taken together form an aliphatic ring having 3 to 20 ring member carbon atoms, a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above aliphatic ring, a hetero ring having 3 to 20 ring member atoms, or a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above hetero ring, together with the 3 -position carbon atom bonded thereto.

6. The indeno-fused naphthopyran of claim 5, wherein B and B’ are each

independently selected from substituted or unsubstituted aryl.

7. The indeno-fused naphthopyran of claims 5 or 6, wherein B and B’ are each independently selected from substituted or unsubstituted phenyl, alkoxyphenyl, halo phenyl, and morpholino phenyl.

8. The indeno-fused naphthopyran of any of claims 5 to 7, comprising the core skeletal structure represented by Formula (Ic):

Formula (Ic) wherein,

m is 0 to 3, and n is 0 to 4; and

R5 independently for each m, and R6 independently for each n, are each independently selected from

i. hydroxyl;

ii. cyano;

iii. (meth)acrylate;

iv. amino or nitrogen-containing heterocycle;

v. a lengthening group L1;

vi. halogen selected from fluoro, chloro, bromo, or iodo;

vii. substituted or unsubstituted alkyl;

viii. substituted or unsubstituted alkenyl;

ix. substituted or unsubstituted alkynyl;

x. haloalkyl;

xi. perhaloalkyl;

xii. boronic ester or boronic acid;

xiii. polyether, polyester, polycarbonate, or polyurethane; xiv. substituted or unsubstituted aryl;

xv. substituted or unsubstituted heterocycloalkyl;

xvi. substituted or unsubstituted heteroaryl; or

xvii. substituted or unsubstituted alkoxy, substituted or unsubstituted

alkylthio, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, ketone, aldehyde, ester, carboxylic acid, carboxylate, amide, urea, siloxane, alkoxysilane, polysiloxane, carbonate, or carbamate.

9. The indeno-fused naphthopyran of claim 8, wherein R6 is at the 10-position and is a lengthening group L1.

10. The indeno-fused naphthopyran of claims 8 or 9, wherein R5 independently for each m and R6 independently for each n, are each independently selected from halogen, alkyoxy, perhaloalkyl, and substituted or unsubstituted aryl.

11. The indeno-fused naphthopyran of any of claims 8 to 10, wherein each lengthening group L1 is independently represented by the following Formula (2),

Formula (2)

- [Si]c -[Qi -[S2]d -[Q2— [S3]e -[Qs -[S4]r ]r - -S5 -P wherein:

(a) Qi, Q2, and Q3 for each occurrence, are independently a divalent group selected from the group consisting of unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted cycloalkyl, substituted cycloalkyl, unsubstituted heterocycloalky, or substituted heterocycloalkyl;

wherein the aryl substituents, heteroaryl substituents, cycloalkyl substituents, and heterocycloalkyl substituents are each independently selected from the group consisting of P, liquid crystal mesogens, halogen, poly(Ci-Ci8 alkoxy), Ci-Cis alkoxycarbonyl, Ci-Cis alkylcarbonyl, Ci-Cis alkoxycarbonyloxy, aryloxycarbonyloxy, perfluoro(Ci-Ci8)alkoxy, perfluoro(Ci-Ci8)alkoxycarbonyl, perfluoro(Ci-Ci8)alkylcarbonyl, perfluoro(Ci-

Ci8)alkylamino, di-(perfluoro(Ci-Ci8)alkyl)amino, perfluoro(Ci-Ci8)alkylthio, Ci-Cis alkylthio, C3-C10 cycloalkoxy, or alkyl;

(b) c, d, e, and f are each independently chosen from an integer of 1 to 20; and each Si, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit selected from the group consisting of:

(i) alkylene, substituted alkylene, haloalkylene, substituted

haloalkylene, -Si(CH2)g-, or -(Si[(CH3)2]0)h-, wherein g for each occurrence is

independently chosen from an integer from 1 to 20; h for each occurrence is independently chosen from an integer from 1 to 16; and the substituents for the alkylene and haloalkylene are independently selected from the group consisting of alkyl or aryl;

(ii) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z’)2-C(Z’)2-, -N(Z)-C(Z)2-, and a single bond, wherein Z for each occurrence is independently selected from the group consisting of hydrogen, alkyl, or aryl, and Z’ for each occurrence is independently selected from the group consisting of alkyl or aryl; and

(iii) -0-, -C(=0)-, -CºC-, -N=N-, -S-, -S(=0)-, -(0=)S(=0)-,

-(0=)S(=0)0-, -0(0=)S(=0)0- and straight-chain or branched Ci-C24 alkylene residue, the Ci-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halogen, or poly-substituted by halogen,

provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other;

(c) P is hydrogen; and

(d) d’, e’ and f are each independently chosen from 0, 1, 2, 3, and 4, provided that the sum of d’ + e’ + f is at least 1.

12. The indeno-fused naphthopyran of any of claims 1 to 11, wherein each alkyl substituent, each aryl substituent, each heterocycloalkyl substituent, and each heteroaryl substituent, is in each case independently selected from halogen, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, perhaloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, hydroxyl, alkylthio, ketone, aldehyde, ester, carboxylic acid, carboxylate, siloxane, alkoxysilane, polysiloxane, amide, amine, carbamate, carbonate, urea, polyester group, polyether group, polycarbonate group, polyurethane group, an acrylate group, a methacrylate group, aryl amine, alkyl amine, cyclic aminos, heteroaromatics, or combinations thereof.

13. The indeno-fused naphthopyran of claim 12, wherein each alkyl substituent, each aryl substituent, each heterocycloalkyl substituent, and each heteroaryl substituent, is in each case independently further substituted with an acrylate group or a methacrylate group.

14. A photochromic composition comprising the indeno-fused naphthopyran of any of claims 1 to 13.

15. A photochromic article comprising the indeno-fused naphthopyran of any of claims 1 to 13, wherein the photochromic article is selected from ophthalmic articles, display articles, windows, mirrors, active liquid crystal cell articles, or passive liquid crystal cell articles; or

wherein the photochromic article is selected from ophthalmic articles, and the ophthalmic articles are selected from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses, or visors; or

wherein the photochromic article is selected from display articles, and the display articles are selected from screens, monitors, or security elements.