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

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[1] 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 unit / S. P. Gromov, E. N. Ushakov, O. A. Fedorova et al. // Journal of Organic Chemistry. — 2003. — Vol. 68, no. 16. — P. 6115–6125. 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. [ DOI ]

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