Journal
RUSSIAN CHEMICAL BULLETIN
Volume 62, Issue 8, Pages 1726-1739Publisher
SPRINGER
DOI: 10.1007/s11172-013-0249-0
Keywords
styryl dye; X-ray diffraction analysis; solid phase [2+2] photocycloaddition; retro [2+2] photocycloaddition; cyclobutanes; NMR spectroscopy
Categories
Funding
- Russian Foundation for Basic Research [11-03-00647]
- Royal Society, UK
- Royal Society of Chemistry, UK
- Photo-chemistry Centre of the Russian Academy of Sciences
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New styryl dye of the 2-benzothiazole 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 X-ray 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 1,2,3,4-tetrasubstituted 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.
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