Spirooxazines: synthesis, structure, spectral and photochromic properties

Lokshin, Vladimir; Samat, A.; Метелица, А. В.

doi:10.1070/rc2002v071n11abeh000763

Cited by 172 publications

(96 citation statements)

References 116 publications

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“…The rate constant of the dark decoloration for 6-NO 2 -BIPS (1',3',3'-trimethyl-6-nitrospiro[2H-1-benzopyran-2,2'-indoline]) equal to 1.54·10 -3 sec -1 , which was obtained under the same conditions (acetonitrile, 293 K) as for compound 1-4, is also given. On one hand, these data show that the introduction of a quaternized pyridine fragment into the benzopyran part of the spiropyran molecule leads to a decrease in the rate of the thermal recyclization by three orders of magnitude, while, on the other, the results support the conclusion that introduction of an electron-withdrawing group into the benzopyran part and the introduction of an electron-donor group into the indoline part of the SPP, as in the case of spirooxazines, which are structural analogs of SPP, also lead to stabilization of the merocyanine form in polar solvents [24].…”

supporting

confidence: 65%

“…The behavior of spiropyrans 1-4, as in the case of spirooxazines [23,24], is probably a function of the dependence of the molecular structure of the merocyanine form, namely, quinoidization or dipolarity, on the electron-withdrawing and electron-donor properties of the substituents in some part of the SPP. The strongly electron-withdrawing NO 2 group in the benzopyran fragment leads to delocalization of the negative charge on the oxygen atom and thereby to stabilization of the dipolar structure of the merocyanine form.…”

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confidence: 98%

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Photo- and thermochromic spiranes. 31.* Photochromic cationic spiropyrans with a pyridinium fragment in the aliphatic side chain*2

Voloshin

Bezugliy

Соловьева

et al. 2008

Chem Heterocycl Comp

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Syntheses are reported for cationic indoline spiropyrans with a quaternized pyridinium fragment in the aliphatic side chain, which display photochromic properties in solution. The major effect of introducing a quaternized pyridinium fragment into the benzopyran part of the spiropyran entails a significant decrease in the rate of thermal relaxation processes.Keywords: cationic indolinospiropyrans, pyridinium fragment, photochromism, electronic absorption spectroscopy.Photochromic organic molecules, some of which are spiropyrans and spirooxazines, have recently been the subject of intensive research due to the use of these compounds in optical recording and data transformation systems, sensors, optical electronics, optical bioelectronics, and transport systems [2-5].However, the limit to improving the characteristics of monofunctional materials has now been reached and attention is being directed toward the development of hybrid polyfunctional materials holding promise for application in molecular electronics.A possible solution of this problem lies in the creation of hybrid polyfunctional materials, which combine structural units responsible for different physicochemical properties such as photochromism and magnetism [6][7][8][9], photochromism and conductivity [10,11], electrical and magnetic properties [12], and optical dichroism and magnetism [13]. A systematic study of both the structure and properties of such units and the feasibility of their combination into a single crystal lattice is required for the development of such materials from molecular units differing in their chemical nature, the investigation of the interaction of such units on each other, and methods for the modification of the properties of the separate units to impart desired properties to the hybrid materials. _______ * For Communication 30 see [1]. * 2 Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov on his 70th jubilee. __________________________________________________________________________________________

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supporting

confidence: 65%

mentioning

confidence: 98%

Photo- and thermochromic spiranes. 31.* Photochromic cationic spiropyrans with a pyridinium fragment in the aliphatic side chain*2

Voloshin

Bezugliy

Соловьева

et al. 2008

Chem Heterocycl Comp

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“…[1][2][3] To increase colorability and durability or tune the chromatic properties of these compounds, a great number of substituted molecules have been synthesized and kinetically studied. Irradiation with suitable wavelengths leads to reversible formation of colored forms (photomerocyanines, PMs) as the result of a change in the conjugated p-system due to an electron cyclization reaction.…”

Section: Introductionmentioning

confidence: 99%

Photochromic, Thermochromic, and Fluorescent Spirooxazines and Naphthopyrans: A Spectrokinetic and Thermodynamic Study

et al. 2008

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The photochromic and thermochromic behavior of four commercially available Reversacol dyes are presented. The compounds studied belong to the class of spirooxazines and naphthopyrans, which are typically thermoreversible photochromic molecules. On stimulation with UV light, these compounds become colored and exhibit spectra which extend over the whole visible region. Increasing the temperature causes spontaneous coloration (thermochromism). Herein, absorption and fluorescence spectra, molar absorption coefficients of the colorless and colored forms, fluorescence and photochemical quantum yields, and kinetic parameters of thermal bleaching (rate constant, frequency factor, and activation energy) are determined in acetonitrile solution. The thermal ground-state reaction is exhaustively described in terms of thermodynamic parameters (equilibrium constant, free energy, enthalpy, and entropy). Temperature effects on photochemical and thermal colorabilities are evaluated. The results indicate that the two spirooxazines are good photochromes below room temperature, whereas they are efficient thermochromic compounds above room temperature. Naphthopyrans are better photochromes but worse thermochromic compounds than spirooxazines.

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“…1 Among the best known photochromic molecules are spirooxazines which have been extensively investigated because they are expected to exhibit greater photostability than their spiropyran analogs. 2 Another advantage is their versatility, allowing modulation of their properties by playing with the position and nature of the substituents. 3 Among the various spirooxazine compounds available, those containing both a phenanthroline moiety and a long alkyl-chain are promising.…”

Section: Introductionmentioning

confidence: 99%

Solvation effect and aggregation of semipermanent spiro[indole-phenanthrolinoxazines] in CH3CN / H2O binary solvent

Gaeva¹,

Metelitsa²,

Voloshin³

et al. 2005

Arkivoc

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Spirooxazines: synthesis, structure, spectral and photochromic properties

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 172 publications

References 116 publications

Photo- and thermochromic spiranes. 31.* Photochromic cationic spiropyrans with a pyridinium fragment in the aliphatic side chain*2

Photo- and thermochromic spiranes. 31.* Photochromic cationic spiropyrans with a pyridinium fragment in the aliphatic side chain*2

Photochromic, Thermochromic, and Fluorescent Spirooxazines and Naphthopyrans: A Spectrokinetic and Thermodynamic Study

Solvation effect and aggregation of semipermanent spiro[indole-phenanthrolinoxazines] in CH3CN / H2O binary solvent

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