New photochromic nonsymmetric bis-spiropyran of the 2,3-dihydro-4-oxonaphtho[2,1-e][1,3]oxazine series

Муханов, Е. Л.; Alekseenko, Yu. S.; Lukyanov, B. S.; Дороган, И. В.; Bezuglyi, S. O.

doi:10.1134/s0018143910030112

Cited by 11 publications

(3 citation statements)

References 5 publications

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“…Such photochromic behavior fully coincides with previous results obtained for iso-structural bis-spiropyran (1) [9]; hence one can expect analogous nature of the absorption bands. This assumption was proved by the quantum-chemical calculations of vertical excitation energies for 2-OR and 1-ORisomers of (2a).…”

Section: Synthesis Of the Compounds (2a-c)supporting

confidence: 90%

“…One can obviously understand that such approach significantly narrows the range of possibly achievable characteristics of spirocompounds. For instance, there were not any examples of observed and well-proved scission of two carbon-oxygen bond in a single bis-spiropyran molecule until quite recently, when we had shown that nonsymmetric bis-spiropyran Figure 2 (1) containing not only indoline but also benzoxazine moiety could undergo opening of two pyran cycles [9].…”

Section: Introductionmentioning

confidence: 99%

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Theoretical and Experimental Study of New Photochromic Bis-Spiropyrans with Hydroxyethyl and Carboxyethyl Substituents

Муханов

Дороган

Chernyshev

et al. 2013

International Journal of Photoenergy

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Two new asymmetrical bis-spiropyrans with nonequivalent spiropyran units have been investigated. Hydroxyethyl and carboxyethyl substituents have been used to improve thermal stability of the photoinduced merocyanine forms of the bis-spiropyrans. 2-Hydroxyethyl substituted compound is characterized by 4 times more stable merocyanine isomer. 2-Carboxyethyl substituent in the hetarene part enables chelation by metal ions and controllably stabilizes the merocyanine from thermal decay. As a result of theoretical modeling and photochemical experiments, it was shown that obtained compounds are perspective prototypes for multistate light-driven switches with improved stability of photoinduced forms.

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Section: Synthesis Of the Compounds (2a-c)supporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Theoretical and Experimental Study of New Photochromic Bis-Spiropyrans with Hydroxyethyl and Carboxyethyl Substituents

Муханов

Дороган

Chernyshev

et al. 2013

International Journal of Photoenergy

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“…Two zwitterionic merocyanine units are provided with a more sensible system as they possess more sensitivity and molar capacity than mono spiropyran. 14 There are a few studies on bis-spiropyran systems and their unique properties, 8,11,14,[18][19][20][21][22][23] but to the best of our knowledge, bis-azospiropyran systems have not been reported yet.…”

mentioning

confidence: 99%

Symmetric Bis-Azospiropyrans: Synthesis, Characterization and Colorimetric Study

Nourmohammadian¹,

Abdi²

2013

Bulletin of the Korean Chemical Society

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Synthesis and characterization of some novel symmetric bis-azospiropyrans are reported in this study. These bis-azospiropyrans are bifunctional chromophores with two spiropyrans linked by a bis-azo extended aromatic system that produce more color strength (large molar absorption coefficient in mero forms) due to appending two azospiropyran chromophores on one molecule. ) at the same conditions. Such high molar absorption coefficients confers high sensitivity to light and more color intensity of mero form, that leads to improvement of their light sensitivity and better discrimination of spiro (OFF) form from mero (ON) ones in molecular switches. The structures were deduced from their MS, FT-IR, and 1 H-NMR spectroscopic data and CHN analysis. All the synthesized photochemically bifunctional compounds revealed fluorescent emission in their colorless form which was faded out after exposing to UV light. Fluorescence quantum yield values of the mero forms were 0.25-0.81 and two high fluorescence quantum yield values (0.60 and 0.81) were found in these series.

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Spectral Properties of a bis-Azospiropyran Complexed with Europium

2015

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New photochromic nonsymmetric bis-spiropyran of the 2,3-dihydro-4-oxonaphtho[2,1-e][1,3]oxazine series

Cited by 11 publications

References 5 publications

Theoretical and Experimental Study of New Photochromic Bis-Spiropyrans with Hydroxyethyl and Carboxyethyl Substituents

Theoretical and Experimental Study of New Photochromic Bis-Spiropyrans with Hydroxyethyl and Carboxyethyl Substituents

Symmetric Bis-Azospiropyrans: Synthesis, Characterization and Colorimetric Study

Spectral Properties of a bis-Azospiropyran Complexed with Europium

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