Design of crystal packings of styryl heterocycles and regularities of [2+2] photocycloaddition in their single crystals 8. Topochemical [2+2] autophotocycloaddition and back reaction in styryl dye of the benzothiazole seriesстатья

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[1] Design of crystal packings of styryl heterocycles and regularities of [2+2] photocycloaddition in their single crystals 8. topochemical [2+2] autophotocycloaddition and back reaction in styryl dye of the benzothiazole series / L. G. Kuz´mina, A. I. Vedernikov, E. K. Lermontova et al. // Russian Chemical Bulletin. — 2013. — Vol. 62, no. 8. — P. 1726–1739. New styryl dye of the 2benzothiazole series was synthesized. The new dye contains two methoxy groups in the benzene ring and tosylate counterion. The [2+2] photocycloaddition (PCA) of the dye was studied in the polycrystalline film and in single crystal. Two modifications of the dye cocrystallizate with hydroquinone differed in the ratio of components were obtained, and their ability to enter PCA was studied. According to the Xray diffraction data, molecular cations of the dye form stack packings either of syn-"head-to-tail" type or relatively isolated stacking dimers. In all cases, the ethylene bonds of the adjacent cations are brought together and antiparallel, favoring PCA to form the centrosymmetric rctt-isomer of 1,2,3,4tetrasubsti tuted cyclobutane. In two cases, the PCA reaction proceeded as the "single crystal-to-single crystal" transformation. Hydrogen bonds in crystals including hydroquinone molecules strengthen the crystal packing retarding the PCA. The back photoreaction (retro-PCA) was detected: it occurs without single crystal decomposition and results in the accumulation of the initial styryl dye in crystal consisting of the cyclobutane derivative. This is the first example of such a transformation in single crystals. [ DOI ]

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