The Nature of the Primary Photochemical Step in Spiropyrans

Kholmanskii, A. S.; Зубков, А. В.; Dyumaev, K. M.

doi:10.1070/rc1981v050n04abeh002617

Cited by 32 publications

(11 citation statements)

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“…Flash photolysis was used to study the mechanism of photochromism for spiropyrans [ 32 ]. First, the ring-closed spiropyran forms the first excited singlet state under UV light radiation, then, the spiro C–O bond breaks, generating the ring-opened intermediate form.…”

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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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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“…The general scheme for such transformations includes the initial formation, during cleavage of the C spiro -O bond, of a [2H]chromene fragment of bipolar form, which can be transformed into a quinoid form with a different configuration for the polymethine chain [15].…”

Section: Chemical Characteristics Of Spiropyransmentioning

confidence: 99%

“…Wide interest in the spiropyrans, which have been known since the beginning of the twentieth century [1], appeared in the middle of the twenties, when their reversible thermochromic properties were discovered [2][3][4], and it increased greatly as their photochromic properties became known [5]. The results of investigations into the structure and characteristics of spiropyrans largely up to 1980 have been discussed and analyzed in existing reviews and monographs [6][7][8][9][10][11][12][13][14][15][16], and they have been partly supplemented by more recent results [17,18].…”

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confidence: 99%

Spiropyrans: Synthesis, Properties, and Application. (Review)

Lukyanov

Lukyanova

2005

Chem Heterocycl Compd

207

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Published data on the synthesis and structural modification of spiropyrans and bisspiropyrans and production of the heteroanalogs of spiropyrans are classified and analyzed. The chemical characteristics of spiropyrans, including complexation of the open-chain isomers and cyclic forms are examined. Special attention is paid to the photochromic characteristics of spiropyrans at interfaces between phases.

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“…As shown in Scheme , spiropyran dyes, including 1 , usually show photochromic properties: a ring-opening isomerization to the MC form by UV irradiation and a ring-closing reverse isomerization to the SP form by visible light irradiation. − In the SP → MC isomerization, the C–O bond cleavage produces a zwitterionic intermediate. Their charges are redistributed to the entire molecule through the π-conjugated CC moiety, producing the MC form.…”

Section: Resultsmentioning

confidence: 99%

Coumarin–Spiropyran Dyad with a Hydrogenated Pyran Moiety for Rapid, Selective, and Sensitive Fluorometric Detection of Cyanide Anion

et al. 2016

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We synthesized a coumarin-spiropyran dyad with a hydrogenated pyran moiety (2), behaving as an off-on type fluorescent receptor for rapid, selective, and sensitive detection of cyanide anion (CN(-)) in aqueous media. The receptor itself shows almost no fluorescence with a quantum yield < 0.01, due to the delocalization of π-electrons over the molecule. Selective nucleophilic addition of CN(-) to the spirocarbon of the molecule rapidly promotes spirocycle opening within only 3 min. This leads to localization of π-electrons on the coumarin moiety and exhibits strong light-blue fluorescence at 459 nm with very high quantum yield (0.52). As a result of this, the receptor facilitates rapid, selective, and sensitive fluorometric detection of CN(-) as low as 1.0 μM.

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The Nature of the Primary Photochemical Step in Spiropyrans

Cited by 32 publications

References 0 publications

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

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

Spiropyrans: Synthesis, Properties, and Application. (Review)

Coumarin–Spiropyran Dyad with a Hydrogenated Pyran Moiety for Rapid, Selective, and Sensitive Fluorometric Detection of Cyanide Anion

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