Étude par Photolyse à Éclairs Répétés de la Photodégradation et de la Colorabilité de Quelques Spiro[Indoline‐Oxazines]

Gautron, R.; Eloy, D; Escaffre, P.; Guglielmetti, R.; Pottier, E.; Tardieu, Pascale

doi:10.1002/bscb.19911000405

Cited by 22 publications

(3 citation statements)

References 10 publications

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“…Qualitative definitions of photo-colourability of this kind of molecule have been previously proposed (Samat et al 1975(Samat et al , 1991Appriou et al 1978;Gaude et al 1991;Gautron et al 1991;Eloy et al 1992), but not of thermo-colourability. The difficulties encountered in giving such definitions earlier derived mainly from the problem of the determination of epM.…”

Section: Thermo-colourability and Photo-colourabilitymentioning

confidence: 99%

A comprehensive kinetic, thermodynamic and photochemical study of some spiro-indoline-oxazines

Favaro

Malatesta²,

Mazzucato

et al. 1995

Proc. Indian Acad. Sci. (Chem. Sci.)

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The thermoreversible photochromic reaction of spiro-indolineoxazines to photo-merocyanines has been studied by stationary spectrophotometric techniques. Two methods are described for determining the molar absorption coefficient of the metastable photomerocyanine and the quantum yield of the colour-forming photoreaction. Kinetic parameters (reaction rate and activation energy) and thermodynamic quantities (equilibrium constant and enthalpy) of the thermal reaction have also been determined. Based on the results obtained, some general correlations between the structure of these molecules and their photochromic and thermochromic properties have been drawn.

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Section: Thermo-colourability and Photo-colourabilitymentioning

confidence: 99%

A comprehensive kinetic, thermodynamic and photochemical study of some spiro-indoline-oxazines

Favaro

Malatesta²,

Mazzucato

et al. 1995

Proc. Indian Acad. Sci. (Chem. Sci.)

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“…Kellmann and colleagues studied the light physics and dynamics of spirooxazines in 1989 [ 41 ]. Pottier et al studied the influence of substituents, heteroatoms, and solvents on the absorption spectra and photochromic kinetics of the ring-opened spirooxazines [ 42 , 43 ]. Wilkinson et al studied the process of photochemical formation for ring-opened spirooxazines in different solvents through picosecond transient absorption and picosecond time-resolved resonance Raman in 1996 [ 44 ].…”

Section: Structure and Mechanism Of Photochromismmentioning

confidence: 99%

Advances in Spiropyrans/Spirooxazines and Applications Based on Fluorescence Resonance Energy Transfer (FRET) with Fluorescent Materials

2017

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Studies on the following were reviewed: (1) the structure of spiropyrans and spirooxazines (two kinds of spiro compounds) under external stimuli and (2) the construction and applications of composite systems based on fluorescence resonance energy transfer (FRET) with fluorescent materials. When treated with different stimuli (light, acids and bases, solvents, metal ions, temperature, redox potential, and so on), spiropyrans/spirooxazines undergo transformations between the ring-closed form (SP), the ring-opened merocyanine (MC) form, and the protonated ring-opened form (MCH). This is due to the breakage of the spiro C–O bond and the protonation of MC, along with a color change. Various novel, multifunctional materials based on photochromic spiropyrans and spirooxazines have been successfully developed because of the vastly differently physiochemical properties posssed by the SP, MC and MCH forms. Among the three different structural forms, the MC form has been studied most extensively. The MC form not only gives complexes with various inorganic particles, biological molecules, and organic chemicals but also acts as the energy acceptor (of energy from fluorescent molecules) during energy transfer processes that take place under proper conditions. Furthermore, spiropyran and spirooxazine compounds exhibit reversible physicochemical property changes under proper stimuli; this provides more advantages compared with other photochromic compounds. Additionally, the molecular structures of spiropyrans and spirooxazines can be easily modified and extended, so better compounds can be obtained to expand the scope of already known applications. Described in detail are: (1) the structural properties of spiropyrans and spirooxazines and related photochromic mechanisms; (2) composite systems based on spiropyrans and spirooxazines, and (3) fluorescent materials which have potential applications in sensing, probing, and a variety of optical elements.

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“…The absorption spectra of the spirooxazines vary greatly according to the substituents in both the indoline and spirooxazine parts of the molecule and on the solvents due to the conjugation of both fragments occurring after the ring opening. ,,,,, In particular, the absorption spectral bands close to 320 and 340 nm observed for the parent/unsubstituted spironaphthoxazine 0 in hexane are associated with the oxazine part of the molecule in its closed form . As reported by Minkovska et al, the absorbance spectra of the substituted compounds are substantially different.…”

Section: Optical Characterization Of Spironaphthoxazines In Solutionsmentioning

confidence: 99%

Photoswitchable Photochromic Chelating Spironaphthoxazines: Synthesis, Photophysical Properties, Quantum-Chemical Calculations, and Complexation Ability

Minkovska,

Hadjichristov,

Neacsu

et al. 2024

ACS Omega

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The stable and efficient photochromic and photoswitchable molecular systems designed from spirooxazines are of increasing scientific and practical interest because of their present and future applications in advanced technologies. Among these compounds, chelating spironaphthoxazines have received widespread attention due to their efficient optical response after complexation with some metal ions being of biomedical interest and environmental importance, as well as their good cycle performance and high reliability, especially by metal ion sensing. In this mini-review, we summarize our results in the design of novel photoswitchable chelating spironaphthoxazines with specific substituents in their naphthoxazine or indoline ring systems in view of recent progress in the development of such molecular systems and their applications as metal ion sensors. The design, synthesis methods, and photoresponse of such spirooxazine derivatives relevant to their applications, as well as quantum-chemical calculations for these compounds, are presented. Examples of various design concepts are discussed, such as sulfobutyl, hydroxyl, benzothiazolyl, or ester and carboxylic acid as substituents in the chelating spironaphthoxazine molecules. Further developments and improvements of this interesting and promising kind of molecular photoswitches are outlined.

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Étude par Photolyse à Éclairs Répétés de la Photodégradation et de la Colorabilité de Quelques Spiro[Indoline‐Oxazines]

Cited by 22 publications

References 10 publications

A comprehensive kinetic, thermodynamic and photochemical study of some spiro-indoline-oxazines

A comprehensive kinetic, thermodynamic and photochemical study of some spiro-indoline-oxazines

Advances in Spiropyrans/Spirooxazines and Applications Based on Fluorescence Resonance Energy Transfer (FRET) with Fluorescent Materials

Photoswitchable Photochromic Chelating Spironaphthoxazines: Synthesis, Photophysical Properties, Quantum-Chemical Calculations, and Complexation Ability

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