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Krayushkin, M. M.; Yarovenko, V. N.; Semenov, S. L.; Shirinyan, V. Z.; Martynkin, A. Yu.; Uzhinov, B. M.

doi:10.1023/a:1021660014609

Cited by 12 publications

(6 citation statements)

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“…23 This diarylethene, unlike, for example, related derivatives of maleic anhydride, 24 does not exhibit photochromic properties either in solution or in the crystalline phase. However, the photoactivity of diarylethenes based on squaric acid derivatives can be restored by introducing bulky heterocycles, such as thienothiophene 23 or thienypyrrole, 25 instead of thiophene or by modifying the bridge. 26 Another example of the critical effect of the size of the bridge was described for perfluorocyclohexenone derivatives containing 2thienyl moieties, 27 which, unlike five-membered analogs, do not exhibit photochromic properties due to steric hindrance between the fluorine atoms of the bridge and the thiophene moieties.…”

Section: ■ Introductionmentioning

confidence: 99%

Structural and Spectral Properties of Photochromic Diarylethenes: Size Effect of the Ethene Bridge

et al. 2017

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The effect of the size of the ethene bridge on the structural and spectral properties of photochromic diarylethenes, which remains a poorly understood phenomenon, was studied as applied to diarylethenes containing unsymmetrical (cyclohexenone and cyclopentenone) and symmetrical (cyclohexene and cyclopentene) ethene bridges. Thiophene, oxazole, and imidazole derivatives were used as aryl moieties. An increase in the size of the ethene bridge in the cycloalkenone series was found to be accompanied by a hypsochromic shift of the absorption maximum of the photoinduced form, whereas no difference was found for cycloalkenes. A detailed analysis of the NMR spectra (including 2D experiments) revealed previously unknown effects associated with the existence of an intramolecular hydrogen bond (CH···N) between the six-membered ethene bridge and the azole substituents. The NMR experimental data obtained were confirmed by DFT quantum chemical calculations and X-ray analysis. It was found that an intramolecular hydrogen bond favors an increase of the quantum yield of the photocyclization reaction.

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Section: ■ Introductionmentioning

confidence: 99%

Structural and Spectral Properties of Photochromic Diarylethenes: Size Effect of the Ethene Bridge

et al. 2017

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“…In the creation of photochromes with condensed thienyl rings, we have synthesized dihetarylethylenes with thieno [3,2-b]pyrroles [4,5], thieno [3,2-b]thiophenes [6], and dithienothiophene [7] rings having various bridges. It was established that photochrome 1 (Scheme 1) with thieno [3,2-b]thiophene fragments [8] undergoes reversible photocyclization to a high degree and also possesses fluorescence of the open form.…”

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confidence: 99%

“…Absorption spectra (1, 3) and luminescence spectra (2, 4) of compound 2 in toluene of the initial forms (1, 2) and after irradiation with UV light (λ = 365 nm)(3,4).…”

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Photochromic Dihetarylethylenes. 21. Synthesis and Photochemical Properties of 1,2-Bis{5-(2-benzothiazolyl)-2-ethylthieno-[2,3-b]thiophen-3-yl}Hexafluorocyclopentene

Krayushkin

Kalik

Kozhinov

et al. 2005

Chem Heterocycl Compd

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has been synthesized for the first time. It was shown that, unlike analogous derivatives of thieno [3,2-b]thiophene, on irradiation with UV light (λ = 313 nm) it did not display photochromic properties, but undergoes an irreversible photoconversion which is accompanied by the display of intense fluorescence. This raises the prospect of using this compound for creating an irreversible photoluminescent recording medium.It was shown previously that photochromic diarylethylenes, in which the perfluorocyclopentene bridge is linked with benzothiophene rings, undergo reversible photocyclization to a high degree [2,3]. In the creation of photochromes with condensed thienyl rings, we have synthesized dihetarylethylenes with thieno[3,2-b]pyrroles [4,5], thieno[3,2-b]thiophenes [6], and dithienothiophene [7] rings having various bridges. It was established that photochrome 1 (Scheme 1) with thieno[3,2-b]thiophene fragments [8] undergoes reversible photocyclization to a high degree and also possesses fluorescence of the open form. It therefore seemed of interest to investigate the photochromic properties of thieno[3,2-b]thiophene derivatives, also possessing a 10-π-electron system, formally analogous to that of benzo[b]thiophene, but with another type of linking the heterocycles. The latter, as is known, causes both a definite similarity and a difference of geometry, and also a difference of the chemical and physicochemical properties of the isomers [9].The synthesis of 1,2-bis{5-(2-benzothiazolyl)-2-ethylthieno[2,3-b]thiophen-3-yl}hexafluorocyclo-pentene (2) was effected according to Scheme 2 starting from 5-ethyl-2-thiophthenecarboxylic acid.4-Bromo-5-ethyl-2-thiophthenecarboxylic acid (3) is formed in 82% yield by the action of an excess of bromine in CHCl 3 on thiophthenecarboxylic acid, and 5-(2-benzothiazolyl)-3-bromo-2-ethylthieno[2,3-b]-thiophene (4) was obtained by the reaction of 3 with o-aminothiophenol in N-methylpyrrolidone by the _______ * For Part 20 see [1]. * 2 Dedicated to V. I. Minkin on his 70th birthday. __________________________________________________________________________________________

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“…2-(3-Indolyl)-2-oxoacetyl chloride (V) was synthesized by the procedure described in [14]. The synthesis of methyl 2-methyl-4H-thieno-[3,2-b]pyrrole-5-carboxylate (VI) was reported in [15].…”

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Synthesis and Structure of 4-Indolyl-5-(thieno[3,2-b]pyrrol-6-yl)imidazoles

et al. 2005

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A procedure was proposed for regioselective acylation of methyl 2-methyl-4H-thieno[3,2-b]-pyrrole-5-carboxylate with 2-(3-indolyl)-2-oxoacetyl chloride. Reactions of the resulting methyl 6-[2-(3-indolyl)-1,2-dioxoethyl]-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate with aromatic aldehydes and ammonium acetate in acetic acid afforded the corresponding methyl 6-[2-aryl-4-(3-indolyl)imidazol-5-yl]-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylates. The structure of methyl 6-[2-(4-chlorophenyl)-4-(3-indolyl)imidazol-5-yl]-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied by X-ray analysis.

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Cited by 12 publications

References 1 publication

Structural and Spectral Properties of Photochromic Diarylethenes: Size Effect of the Ethene Bridge

Structural and Spectral Properties of Photochromic Diarylethenes: Size Effect of the Ethene Bridge

Photochromic Dihetarylethylenes. 21. Synthesis and Photochemical Properties of 1,2-Bis{5-(2-benzothiazolyl)-2-ethylthieno-[2,3-b]thiophen-3-yl}Hexafluorocyclopentene

Synthesis and Structure of 4-Indolyl-5-(thieno[3,2-b]pyrrol-6-yl)imidazoles

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