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Title of Journal: Russ Chem Bull

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Abbravation: Russian Chemical Bulletin

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Springer US

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DOI

10.1016/0749-596x(88)90048-4

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1573-9171

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Design of crystal packings of styryl heterocycles

Authors: L G Kuz’mina A I Vedernikov E Kh Lermontova J A K Howard M V Alfimov S P Gromov
Publish Date: 2014/04/25
Volume: 62, Issue: 8, Pages: 1726-1739
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Abstract

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“headtotail” 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 rcttisomer of 1234tetrasubstituted cyclobutane In two cases the PCA reaction proceeded as the “single crystaltosingle crystal” transformation Hydrogen bonds in crystals including hydroquinone molecules strengthen the crystal packing retarding the PCA The back photoreaction retroPCA 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


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