Photophysics and kinetics of two photochromic indolinospirooxazines and one indolinospironaphthopyran

Kellmann, A.; Tfibel, F.; Dubest, Roger; Levoir, P.; Aubard, J.; Pottier, E.; Guglielmetti, R.

doi:10.1016/1010-6030(89)87106-0

Cited by 109 publications

(63 citation statements)

References 20 publications

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“…The open form of compound 12 presents a better thermal stability than the open form of compound 11, due to the stereoelectronic effects (increasing of the inductive effect and decreasing of the steric hindrance). This result is compatible with the zwitterionic character of photomerocyanines [24].…”

supporting

confidence: 84%

Synthesis of Thiophene‐Substituted Spiropyrans and Spirooxazines, Precursors of Photochromic Polymers

Moustrou¹,

Samat²,

Guglielmetti³

et al. 1995

Helvetica Chimica Acta

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The synthesis of spiropyrans 11 and 12 and spirooxazines 15-17 containing a thiophene moiety is described. Two different synthetic approaches were used. The spectrokinetic properties of these new compounds are reported.Introduction. - [8]. The modification of the optical, electronic, and electrochemical properties of these materials is the main goal of research efforts. Thus, the synthesis of new precursor structures to prepare new conducting materials remains a current challenge for organic chemists. The typical photochromic compounds such as spiropyrans and spirooxazines are well-known for their photosensitive properties [9] [lo] (Scheme I ) . The exposure of these organic compounds to UV light results in a color change. This transformation between the closed form, which is colorless, and the colored open form (photomerocyanine) proves attractive to affect potentially the polymer properties.In this paper, we report the synthesis of spiro [benzopyran-indoles] and spiro[indole-

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supporting

confidence: 84%

Synthesis of Thiophene‐Substituted Spiropyrans and Spirooxazines, Precursors of Photochromic Polymers

Moustrou¹,

Samat²,

Guglielmetti³

et al. 1995

Helvetica Chimica Acta

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“…The constants, k 1 , and k 2 , were higher than those observed at the same temperature in the dark. With respect to reaction (1), the photoisomerization from SNO to MC induced forming MCH + because the quantum yield of the photoisomerization is reported to be a certain value, 0.2−0.4 [29,30].…”

Section: Reaction During Uv Irradiationmentioning

confidence: 99%

Photochromic behavior of spironaphthoxazine in metal ion-containing solutions

Nishikiori

Takamura

Shimamura

et al. 2011

Journal of Photochemistry and Photobiology A: Chemistry

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The isomerization and metal chelation of spironaphthoxazine (SNO) in ethanol solutions have been investigated by measuring the UV-vis absorption spectra as a function of time.The protonated species of merocyanine (MC), an isomer of SNO, was gradually formed in the solutions containing SNO and aluminum ions in the dark. The proton was provided by the reaction of the aluminum ions with a slight amount of water contained in the ethanol solvent.The protonated species was slowly transformed into the aluminum chelate complex of MC by ligand exchange of the ethanol-solvated aluminum for MC in the dark. UV irradiation promoted the isomerization and chelation without forming the protonated species. The spectroscopic analysis with various compositional ratios of SNO and aluminum ions revealed that one aluminum ion was coordinated to three bidentate MC ligands in the ethanol solution.

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“…It is well-known that SO exhibits photochromic, [8][9][10][11] thermochromic 11,12 and acidichromic 13,14 properties in solution and in various matrices. The photoproduced merocyanine (M) thermally reconverts to the original spiro isomer (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Unexpected chromogenic properties of 1,3,3-trimethylspiro(indoline-2,3′-[3H]naphtho [2,1-b][1,4]oxazine) in the solid phase: photochromism, piezochromism and acidichromism

et al. 2004

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New chromogenic properties of a spirooxazine {1,3,3-trimethylspiro(indoline-2,3 0 -[3H]naphtho[2,1-b][1,4]-oxazine), SO} are presented in this work. This molecule was found to be photochromic and piezochromic in the pure microcrystalline solid phase and also exhibited acidichromism when kept in contact with a hydrogen-donating solid phase. Photochromism was observed under continuous UV irradiation. Biexponential thermal bleaching followed the interruption of irradiation. Piezochromism was detected by applying a mechanical force to the solid powder, using either a hydraulic press or manual crushing. After discontinuing pressure, biexponential bleaching kinetics were observed. The biexponential nature of the fading processes is interpreted in terms of merocyanine (M) micro-spot formation inside the crystalline phase. The third chromogenic property of the solid spirooxazine, acidichromism, is due to the extraction of protons from an acidic solid matrix, alpha zirconium phosphate [a-Zr(HPO 4 ) 2 ÁH 2 O]. Proton transfer to SO in the solid phase causes the appearance of a purple colour. The spectral evolution is qualitatively similar to that observed in CH 3 CN solution when HClO 4 is added at room temperature and in the dark. Temporal evolution of the colour bands, in both solid and liquid phases, is interpreted in terms of an initial protonation, inducing ring-opening, and a second protonation, leading to a colourless product.

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Photophysics and kinetics of two photochromic indolinospirooxazines and one indolinospironaphthopyran

Cited by 109 publications

References 20 publications

Synthesis of Thiophene‐Substituted Spiropyrans and Spirooxazines, Precursors of Photochromic Polymers

Synthesis of Thiophene‐Substituted Spiropyrans and Spirooxazines, Precursors of Photochromic Polymers

Photochromic behavior of spironaphthoxazine in metal ion-containing solutions

Unexpected chromogenic properties of 1,3,3-trimethylspiro(indoline-2,3′-[3H]naphtho [2,1-b][1,4]oxazine) in the solid phase: photochromism, piezochromism and acidichromism

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