- One-pot synthesis of photochromic naphthopyrans in the solid state
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matrix presented p-TsOH-catalyzed condensation reactions of 1,1-diaryl-2-propyn-1-ol (1) and 2-naphthol (2) in the solid state gave 3,3-diaryl-3H-naphtho[2,1-b]pyran (6) via Claisen rearrangement. Similar reactions of 1 with 2,6-(7) and 2,7-dihydroxynaphthalenes (8) afforded naphthodipyrane derivatives 9 and 10, respectively. Bis-naphthopyran derivatives 12 were also obtained by the reaction of 1,1,6,6-tetraaryl-2,5-hexadiyn-1,6-diol (11) and 2-naphthol (2) in the solid state.
- Tanaka, Koichi,Aoki, Hiroko,Hosomi, Hiroyuki,Ohba, Shigeru
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Read Online
- Photochromism of diarylnaphthopyrans
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A series of 3,3-diaryl-3H-naphtho[2,1-b]pyrans were prepared and their photochromic properties measured in plastic matrix. The influence of a variety of substituents on color, intensity, and fade were studied.
- Van Gemert,Bergomi,Knowles
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Read Online
- Photophysics and kinetics of naphthopyran derivatives, part 3: A general procedure to uniquely identify the kinetic and spectroscopic parameters of ABC(2k,2φ) systems and application to naphthopyran reactions
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A new procedure has been developed with the aim of determining the kinetic and spectroscopic parameters of any photochemical systems of the generic ABC(2k,1φ) and ABC(2k,2φ) types. General expressions of the colorability and the equilibrium concentration ratio of two (of the three involved) species at a photostationary state or a state of thermal equilibrium have been derived. The procedure has been successfully applied to achieve unique identifiability for the seven sequences of the ABC(2k,1φ and 2φ) type that may represent naphthopyran dynamics. It is demonstrated that the reactivity of this particular compound is certainly described by a higher kinetic level than those (three or four reaction steps) considered in the present study.
- Maafi,Brown
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Read Online
- Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic gem-Diacetates: Synthesis of Chromene-Based Natural Products and Exploration of Photochromic Properties
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Palladium-catalyzed allylic alkylation reactions of allylic gem-diacetates are rarely explored. This work unveils an unusual chemical reactivity pattern of allylic gem-diacetates and establishes them as new prototypes to synthesize complex benzo[f]chromene systems. Under the reaction conditions, the diacetates behave as 1,3-dicationic equivalents and undergo a [3 + 3] heteroannulation with 2-naphthols (and meta-substituted phenols) to produce novel polycyclic chromenes possessing spiro-, tri-, and tetrasubstituted carbon centers. The versatility of the method is demonstrated in the synthesis of several chromene-based bioactive natural products. Further, interesting photochromic properties of the new classes of benzo[f]chromenes are also discovered.
- Kumar, Prashant,Kumar, Pravesh,Ramasastry, S. S. V.,Venkataramani, Sugumar
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p. 963 - 970
(2022/01/19)
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- Spectral manifestation of protonation of photochromic naphthopyrans
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The formation of proton complexes of the photoinduced colored open form of naphthopyrans in solutions was first discovered and investigated by spectral-kinetic method. The complexes exhibit a new absorption band in the visible region, which is bathochromically shifted relative to the absorption band of the photoinduced colored open form. With an increase in the concentration of perchloric or hydrochloric acid, this long-wavelength absorption band appears immediately after the addition of acids to solutions of photochromic compounds. The protonation efficiency depends on the strength of the acids.
- Barachevsky, Valery А.,Gorelik, Alexander М.,Kobeleva, Оlga I.,Valova, Тatyana М.,Venidiktova, Оlga V.
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- Facile access to 2,2-diaryl 2: H -chromenes through a palladium-catalyzed cascade reaction of ortho -vinyl bromobenzenes with N -tosylhydrazones
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A palladium-catalyzed cascade reaction of ortho-vinyl bromobenzenes with N-tosylhydrazones has been developed, which provides a facile approach to 2,2-disubstituted 2H-chromenes. The migration of palladium from the aryl to vinyl position is crucial, as the in situ produced vinyl palladium intermediate could further react with diazo compounds to generate the reactive species for the sequential annulation. This journal is
- Huang, Xueliang,Yu, Yinghua,Zhang, Heng
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supporting information
p. 5115 - 5119
(2020/07/23)
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- Access to Electron-Deficient 2,2-Disubstituted Chromanes: A Highly Regioselective One-Pot Synthesis via an Inverse-Electron-Demand [4 + 2] Cycloaddition of ortho-Quinone Methides
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We report the one-pot synthesis of 2,2-disubstituted chromanes with electron-withdrawing substituents. This reaction provides a simple yet efficient route to a wide range of electron-deficient chromanes in high yield and excellent regioselectivity. The reaction of salicylaldehyde with 1,1-disubstituted ethylenes smoothly furnishes these electron-deficient chromanes, which can be further transformed into functionalized chromanes or chromene. For example, BW683C was effectively synthesized from 5-chlorosalicylaldehyde with 4-chlorostyrene in two steps in excellent yield. The present reaction thus provides versatile access to functionalized electron-deficient chromanes and chromenes and therefore constitutes a promising tool for the synthesis of biologically and photochemically active molecules.
- Tanaka, Kenta,Kishimoto, Mami,Asada, Yosuke,Tanaka, Yuta,Hoshino, Yujiro,Honda, Kiyoshi
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p. 13858 - 13870
(2019/11/03)
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- Temperature-controlled divergent synthesis of 4-alkoxy- or 4-alkenyl-chromanes via inverse electron-demand cycloaddition with in situ generated ortho-quinone methides
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The temperature-controlled divergent synthesis of 4-alkoxy- or 4-alkenyl-chromanes via inverse electron-demand cycloaddition with in situ generated ortho-quinone methides under identical reaction conditions except for thermal condition has been developed. At room temperature, the reaction generated 4-methoxychromanes, whereas the reaction performed at room temperature to 100 °C gave 4-alkenylchromanes. Trifluoromethanesulfonic acid was efficiently suitable in the reaction to give the 4-substituted chromanes. This divergent synthetic strategy exhibits a new method giving carbon–carbon or carbon–oxygen bond by controlling the reaction temperature.
- Tanaka, Kenta,Kishimoto, Mami,Hoshino, Yujiro,Honda, Kiyoshi
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supporting information
p. 1841 - 1845
(2018/04/11)
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- Experimental and theoretical investigations of cyanide detection using a photochromic naphthopyran
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Photochromic naphthopyran derivatives were synthesised for anion recognition applications. The crystal structure, experimental and theoretical investigation of photochromic and anion sensing properties of a simple naphthopyran derivative were investigated. The naphthopyran derivative displayed good fatigue resistance and selective sensing response towards cyanide ions. The mechanism of complex formation was suggested based on NMR studies. Theoretical calculations were performed to understand the experimental results. An excellent correlation between the theoretical and experimental data was observed.
- Sahoo, Priyaranjan,Prakash, Kunal,Kumar, Satish
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p. 183 - 192
(2017/01/10)
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- A Simple and Versatile Strategy for Rapid Color Fading and Intense Coloration of Photochromic Naphthopyran Families
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Benzo-annulated chromenes, i.e., naphthopyrans, are well-known photochromic molecules that undergo photochemical ring-opening reactions to form two colored open-ring isomers, the transoid-cis and transoid-trans forms, upon light irradiation. Though the transoid-cis form returns thermally to the uncolored closed form, the fading rate of the transoid-trans form is extremely slow because of its higher thermal stability. This slow fading behavior of the transoid-trans form is responsible for the persistence of residual color for several minutes to hours, and prevents the application of such molecules to fast photoswitching materials. We have found a new simple and versatile strategy to substantially reduce the amount of the undesirable long-lived colored transoid-trans form by introducing an alkoxy group at the 1-position of azino-fused chromenes, i.e., 8H-pyranoquinazolines. The alkoxy group effectively reduces the formation of the transoid-trans form due to C-H···O intramolecular hydrogen bonding in the transoid-cis form. Moreover, the introduction of a condensed aromatic ring at the 3-position was found to be effective to increase the photosensitivity of the ring-opening reaction. This strategy can also be applied for naphthopyran derivatives and is useful for the development of fast photoresponsive photochromic lenses and fast photoswitching applications such as dynamic holographic materials and molecular actuators.
- Inagaki, Yuki,Kobayashi, Yoichi,Mutoh, Katsuya,Abe, Jiro
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p. 13429 - 13441
(2017/10/05)
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- Boronic acid/Br?nsted acid co-catalyst systems for the synthesis of 2: H -chromenes from phenols and α,β-unsaturated carbonyls
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Protocols for the synthesis of substituted 2H-chromenes from α,β-unsaturated carbonyls and phenols are described. Optimal combinations of arylboronic acids and Br?nsted acids have been identified, such that both can be employed in catalytic quantities to accelerate these condensations. The method has been used to synthesize a variety of substituted 2H-chromenes, as well as photochromic naphthopyrans. The use of pentafluorophenylboronic acid and diphenylphosphinic acid enabled an expansion of the electrophile scope to include α,β-unsaturated ketones. Hall's 'phase-switching' of boronic acids has been exploited to achieve the separation of the two co-catalysts from unpurified reaction mixtures by a simple liquid-liquid extraction.
- Dimakos, Victoria,Singh, Tishaan,Taylor, Mark S.
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p. 6703 - 6711
(2016/07/21)
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- First observation for dynamic solvent effect in ionic liquids
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We observed pressure effects on the rate of thermal fading of colored chromene 1 photochemically generated from 2 in ionic liquids. The reaction rates were retarded with increasing pressure in [C4-mim][CS], [bzl-mim][Tf2N], and [mnp-mim][Tf2N], whereas the reaction rate increased with pressures in [C4- mim][Tf2N]. These pressure-induced retardations, so-called dynamic solvent effects, result from the slow thermal fluctuations of solvents.
- Kitaoka, Satoshi,Nobuoka, Kaoru,Miura, Junji,Ohga, Yasushi,Ishikawa, Yuichi
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supporting information
p. 385 - 387
(2016/05/09)
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- Convenient synthesis of naphthopyrans using montmorillonite K-10 as heterogeneous catalyst
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A simple and mild procedure for the synthesis of different naphthopyrans providing high yields in a short reaction time was reported. The reaction of propargylic alcohols with α- or β-naphthol and dihydroxy naphthalenes in the presence of montmorillonite K-10 was studied. This reaction afforded high yields of the corresponding naphthopyrans. In addition, a number of new phenylene and biphenylen-linked bisnaphthopyrans were synthesized providing excellent yields via the one-pot reaction of bis-propargyl alcohols with β-naphthol.
- Hosseinzadeh, Rahman,Mohadjerani, Maryam,Javad Ardestanian, Mohammad,Naimi-Jamal, Mohammad Reza,Lasemi, Zahra
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p. 1081 - 1089
(2014/11/08)
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- Synthesis and photochromic properties of spiro[naphthopyran-7′H- benzocyclohepta-5′,8′-dienes]
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A series of spironaphthopyrans has been synthesised by the acid-catalysed condensation between either a substituted 1-naphthol or 2-naphthol and the propargylic alcohol derived from the addition of lithium trimethylsilylacetylide to a 7H-benzocycloheptan-7-one with subsequent in situ silyl group removal. The photochromism of the novel spironaphthopyrans was characterised by a bathochromically shifted λmax coupled with a relatively quick initial fade of the photogenerated species relative to the comparable diphenyl substituted model compounds. After initial fading a relatively intense residual colour persisted for the spironaphthopyrans.
- Crossley, Daniel L.,Gabbutt, Christopher D.,Mark Heron,Kay, Paul,Mogstad, Martin
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experimental part
p. 62 - 68
(2012/07/03)
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- The synthesis and properties of vinyl substituted naphthopyrans and their styrene copolymers
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A comprehensive series of mono-, di- and tri-bromo-3H-naphtho[2,1-b]pyrans was synthesised by the traditional union of a 2-naphthol with an alkynol. The bromine atom(s) in these naphthopyrans was readily replaced by a vinyl group using a Suzuki coupling reaction with vinyl boronic anhydride pyridine complex. The efficiency of the Suzuki vinylation reaction decreases with the increasing number of bromine atoms to be substituted. The vinylnaphthopyrans served as styrene analogues and readily underwent a thermally initiated free radical addition co-polymerisation with styrene to efficiently afford low molecular weight poly(styrene-co-naphthopyrans). The photochromic response of the bromonaphthopyrans and vinylnaphthopyrans followed the established colour-structure relationships for photochromic naphthopyrans. The photochromic response of toluene solutions of the poly(styrene-co-naphthopyrans) was characterised by a hypsochromic shift of the λmax relative to that recorded for the vinylnaphthopyran monomers. Increased half-lives were noted for the copolymers derived from the bis- and tris-vinylnaphthopyrans where some degree of crosslinking was expected. A further hypsochromic shift in λmax resulted for the thin films of the poly(styrene-co- naphthopyrans). Of particular note was the behaviour of the 3-(2-vinylphenyl)-3- phenylnaphthopyran which gave the typical yellow colour of the photomerocyanine coupled with the predictable large half-life. However, all photochromism of this naphthopyran was lost upon polymerisation suggesting that an alternative pathway supervenes in the expected polymerisation sequence.
- Blackwell, Catherine J.,Gabbutt, Christopher D.,Guthrie, James T.,Heron, B. Mark
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experimental part
p. 408 - 420
(2012/08/28)
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- Synthesis and photochromic properties of substituted naphthopyran compounds
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A group of 3,3-diaryl-3H-naphtho[2,1-b]pyran compounds with functional substituents at the 5- and 6-positions of the naphthopyran skeleton and the para positions at the 3-aryl moieties were prepared through condensation reactions between 2-naphthol derivatives and 1,1-diarylprop-2-yn-1-ol derivatives. The chemical structures of the compounds were confirmed by NMR and MS. The crystal structure of 3,3-diphenyl-6-morpholino-3H-naphtho[2,1-b]pyran (4b) was determined and the relationship between the pyran substructure and photochromism was discussed. The photochromic properties were studied as well, and decoloration kinetics of colored forms was fitted to the biexponential model. Among these compounds, 4b was considered to be the best one due to the large ΔOD of colored form, which is one of the most important properties used in the photochromic material.
- Wang, Zhen,Meng, Qinghua,Zhang, Zhihui,Fu, Dingliang,Zhang, Wanbin
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experimental part
p. 2246 - 2250
(2011/04/22)
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- Functional mesoporous aluminosilicate nanoparticles as host material to fabricate photo-switchable polymer films
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Precisely nano-sized aluminosilicate particles (average diameter size 50 to 80 nm) with tailor-made internal surface polarity are suitable as host material for photochromic dyes of the chromene type in order to produce optical transparent photoswitchable polymer films. The sophisticated host material does accomplish two important requirements for a technical application, appropriate internal space for the light induced reversible switching process of the adsorbed dye and suppression of disturbing chemical reactions. The adjustment of the internal surface polarity of the host material was achieved by silane reagents which could be observed by means of specific solvatochromic probes. The Royal Society of Chemistry 2011.
- Kahle, Ingolf,Troeber, Oliver,Trentsch, Sabine,Richter, Hannes,Gruenler, Bernd,Hemeltjen, Steffen,Schlesinger, Maik,Mehring, Michael,Spange, Stefan
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experimental part
p. 5083 - 5088
(2011/10/12)
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- A strategy for the design of photochromic naphthopyrans with large optical density at photosteady state and fast fading speed at ambient temperature in the dark
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A photochromic naphthopyran system in which both optical density and fading speed of colored forms are significantly increased has been described. 3-Aryl-3-(α-naphthalene)-3H-naphtho[2,1-b]pyrans showed thermal stability, and a large optical density of colored forms was obtained at ambient temperature. By attachment of an alkoxyl group to the α-naphthalene group, the fading speed of colored forms was dramatically increased, and the fading speed was increased with increase of the length of alkoxyl chain. The generic nature of the system is beneficial for both the design of naphthopyran molecules with large optical density and fast fading speed at ambient temperature and applications.
- Guo, Kunpeng,Chen, Yi
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scheme or table
p. 4193 - 4197
(2011/07/30)
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- Photochromic properties of naphthopyrans - PMMA thin film
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A class of naphthopyran derivatives (3a-10a) with electron-donating and electron-acceptor substituent is prepared by condensation of 1,2-diaryl-2-propyn-1-ol with -naphthol in the presence of pyridinium para-toluenesulfonate (PPTS) as catalyst. All compounds go ring-opening isomerization in polymethylmethacrylate (PMMA) matrix with UV light irradiation (30watt) and the maximum absorption of ring-opening isomers is at the range of 426-556nm. Ring-opening isomers are completely back to ring-closing isomers when samples are kept in darkness, the bleach rate of ring-opening isomers in PMMA film increased significantly when temperature is more than 45C. Fatigue testing showed that no significant change of optical density was detected after 10cycles.
- Guo, Kunpeng,Chen, Yi
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experimental part
p. 62 - 71
(2010/04/02)
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- Photophysics and kinetics of naphthopyran derivatives, Part 2: Analysis of diarylnaphthopyran kinetics. Degeneracy of the kinetic solution
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The photocoloring and fading kinetics of the photochromic 3,3-diphenyl-3H-naphtho|2,1-b|pyran (NPY) have been analyzed using a kinetic treatment for three related species recently developed by us (Int J Chem Kinet 2005, 37(3), 162). The concepts of identifiability and distinguishability are developed with respect to the elucidation of the NPY kinetics. We find that neither set of kinetic data on its own, nor the two data sets combined, allow the true mechanism to be distinguished. In addition, even for a chosen mechanism, there exist degenerate sets of parameters i.e. the solutions are also unidentifiable. A discussion of the limits and uniqueness of the results' interpretation is presented.
- Maafi,Brown
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p. 717 - 727
(2008/04/18)
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- A new application of high-viscosity kinetics. An attempt to identify a site of solvent reorganizations around a reactant
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Thermal fading of a colored species photochemically generated from so-called chromenes was kinetically studied in highly viscous media. The reaction was retarded by an increase in viscosity at viscosities higher than 102 Pas. We propose to use substituent dependence of this retarding effect as a tool to identify the main site of solvent reorganizations around the reactant molecule in the activation step.
- Sugita, Keijiro,Goto, Yoshitaka,Ono, Mikiko,Yamashita, Kazumi,Hayase, Kayoko,Takahashi, Toru,Ohga, Yasushi,Asano, Tsutomu
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p. 1803 - 1806
(2007/10/03)
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- Facile One-Pot Synthesis of Photochromic Pyrans
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(Equation presented) Photochromic pyrans, including [3H]naphtho[2,1-b] pyrans, [2H]naphtho[1,2-b]pyrans, indeno-fused naphtho[1,2-b]pyrans, and heteroannulated pyrans, were synthesized in excellent yields through a facile one-pot procedure by reaction of propargyl alcohol and naphthol or phenol derivatives in the presence of 5 mol% PPTS and 2 equiv of (MeO)3CH. Symmetrical and nonsymmetrical bispyrans can also be prepared using the protocol.
- Zhao, Weili,Carreira, Erick M.
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p. 4153 - 4154
(2007/10/03)
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- An experimental attempt to identify a moving molecular moiety in a solvent matrix
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It was experimentally demonstrated that microscopic friction between a reactant molecule and the surrounding solvent during a unimolecular structural change increased with increasing bulkiness of substituents and it is suggested that this dependence can be used to identify a moving molecular moiety in the reactant inside of a solvation shell.
- Goto, Yoshitaka,Sugita, Keijiro,Takahashi, Toru,Ohga, Yasushi,Asano, Tsutomu
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p. 618 - 619
(2007/10/03)
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- Photochromic naphtho [2,1-b]pyran compounds containing bithienyl or terthienyl substituents, process for their manufacture, and photochromic materials and articles obtained
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The photochromic compounds of the invention correspond to the formula: in which Th2represents a bithienyl group in one of the positions 5 to 10 of the naphthenic ring system system, R1denotes a bithienyl or trithienyl group and R2denotes a bithienyl, trithienyl, aryl, naphthyl, thienyl, furyl, pyrrolyl or N-alkylpyrrolyl group.
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- Complete assignment of the 1H, 13C and 19F NMR spectra of fluoro-substituted 3H-naphthopyrans
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The complete assignment of the 1H, 13C and 19F NMR spectra of eight fluoro-substituted 3H-naphthopyrans was achieved by the concerted application of homonuclear (1H-1H) and heteronuclear (13C-1H and 19F-1H) correlations. Copyright
- Delbaere, Stephanie,Teral, Yannick,Bochu, Christophe,Campredon, Mylene,Vermeersch, Gaston
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p. 159 - 162
(2007/10/03)
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- Photochromic behaviour of Bis[4-(N,N-dimethylamino)phenyl]-substituted 3H-naphtho[2,1-b]pyran and 2H-1-Benzopyran
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The photochromic behaviour of 3,3-bis[4-(N,N-dimethylamino)phenyl]-3H-naphtho[2,1 -b]pyran (2) and 2,2-bis[4-(N,N-dimethylamino)phenyl]-2H-1 -benzopyran (3) has been studied by flash photolysis and compared to 3,3-diphenyl-3H-naphtho[2,1 -b]pyran (i) in order to delineate effects due to the N,N-dimethylamino groups.
- Harie, Guenaelle,Samat, Andre,Guglielmetti, Robert,De Keukeleire, Denis,Saeyens, Wim,Van Parys, Inge
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p. 3075 - 3078
(2007/10/03)
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- Synthesis and Photochromic Behaviour of Naphthopyrans, Pyranoquinolines, Pyranoquinazolines and Pyranoquinoxalines
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New chromenes annulated with different six-membered azaheterocycles were prepared, i.e., the 3H-pyrano[3,2-f]quinolines 9/10 and 14, the 8H-pyrano[2,3-h]isoquinoline 11, the 8H-pyrano[3,2-f]quinazoline 12, the 8H-pyrano[3,2-f]quinoxaline 13, and the 2H-pyrano[2,3-f]isoquinoline 15. The synthesis was achieved using conveniently substituted α,β-unsaturated aldehydes and organotitanium intermediates arising from azaheterocyclic phenols. Their photochromic behaviour (photocolouration yield, UV/VIS spectrum of photomerocyanines, rate constant of thermal bleaching) were studied besides those of corresponding naphthopyrans. The heterocycle effect and the role of substituents in the pyran moiety were investigated quantitatively through the study of the photochromic properties and the solvent effects. Diaryl-substituted azino-fused chromenes, especially isoquinoline derivatives, exhibit increased colourabilities and bathochromically shifted spectra for photomerocyanines which open up new prospects for photochromic applications.
- Pozzo, Jean-Luc,Samat, Andre,Guglielmetti, Robert,Dubest, Roger,Aubard, Jean
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p. 725 - 738
(2007/10/03)
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- Photochromic naphthopyran compounds
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Described are novel reversible photochromic naphthopyran compounds, examples of which are compounds substituted at the 3 position of the pyran ring with (i) an aryl substituent and (ii) a phenyl substituent having a 5- or 6-member heterocyclic ring fused at the number 3 and 4 carbon atoms of the phenyl substituent. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline) type compounds, are also described.
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- Photochromic naphthopyran compounds
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Described are novel reversible photochromic diaryl-3H-naphtho[2,1-b]pyran compounds having a substituted or unsubstituted, five or six member heterocyclic ring fused to the g, i, or l side of the naphthopyran. The heterocyclic ring contains an oxygen or nitrogen atom and is attached to the number 5, 6, 7, 8, 9, or 10 carbon atom of the naphtho portion of the naphthopyran. Also described are organic host materials containing such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline)oxazine-type compounds, are also described.
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- Photochromic substituted naphthopyran compounds
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Described are novel reversible photochromic 3H-naphtho[2,1-b]pyran compounds, of the following graphic formula: STR1 wherein R1 is hydrogen or alkyl, R2 is hydrogen or preferably a carboalkoxy group and R3 is hydrogen or preferably an alkyl group, provided that either R1 or R2 is hydrogen, and B and B' are the aryl groups phenyl or naphthyl, a heterocyclic aromatic group or together form a spiro adamantylene group. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(oxazine) type compounds, are also described.
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- Benzopyran compounds
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Described are novel reversible photochromic benzopyran compounds, examples of which are compounds having the 2,3 position of a benzofurano or benzothieno group fused to the f, g, or h side of the benzopyran, or a benzo group fused to the f side of the benzopyran, and (i) a substituted or unsubstituted phenyl and (ii) a substituted or unsubstituted benzothienyl or benzofuranyl group attached (via the 2 or 3 position of the group) at the 2 position of the pyran ring. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel benzopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro (indoline) type compounds, are also described.
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- Photochromic naphthopyran compounds
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Described are novel reversible photochromic naphthopyran compounds, examples of which are 3-aryl-3-arylalkenyl naphthopyrans. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline) type compounds, are also described.
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- Photochromic naphthopyran compounds
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Described are novel reversible photochromic naphthopyran compounds having at least one ortho substituted phenyl group at the 3-position of the pyran ring. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indolino)-oxazine type compounds, are also described.
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