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Novel photoswitchable receptors: Synthesis and cation-induced self-assembly into dimeric complexes leading to stereospecific [2+ 2]-photocycloaddition of styryl dyes containing a 15-crown-5 ether unitстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 18 июля 2013 г.
- Авторы: Gromov S.P., Ushakov E.N., Fedorova O.A., Baskin I.I., Buevich A.V., Andryukhina E.N., Alfimov M.V., Johnels D., Edlund U.G., Whitesell J.K., others
- Журнал: Journal of Organic Chemistry
- Том: 68
- Номер: 16
- Год издания: 2003
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 6115
- Последняя страница: 6125
- DOI: 10.1021/jo034460x
- Аннотация: Styryl dyes 4a−e containing a 15-crown-5 ether unit and a quinoline residue with a sulfonatoalkyl or sulfonatobenzyl N-substituent were synthesized. The relationship between the photochemical behavior of these dyes and their aggregates derived from complexation with Mg2+ in MeCN was studied using 1H NMR and absorption spectroscopy. The E-isomers of 4a−e were shown to form highly stable dimeric (2:2) complexes with Mg2+. Upon irradiation with visible light, the dimeric complexes undergo two competing photoreactions, viz., geometric E → Z isomerization, resulting in an anion-capped 1:1 complex of the Z-isomer with Mg2+ and stereospecific syn-head-to-tail [2+2]-cycloaddition, affording a single isomer of bis-crown-containing cyclobutane. The N-substituent in the dye has a dramatic effect on the photochemical behavior of the dimeric complex. Molecular dynamics and semiempirical quantum-chemical calculations were carried out to interpret the observed photocycloaddition in the dimer. Conformational equilibria for the dimer of (E)-4b were analyzed using 1H NMR spectroscopy.
- Добавил в систему: Баскин Игорь Иосифович