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Issue 39, 2016
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Peculiarities of styryl dyes of the benzoselenazole series crystal packings and their influence on solid phase [2 + 2] photocycloaddition reaction with single crystal retention

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Abstract

New styryl dyes of the 2-benzoselenazole series which contain iodide, triiodide, and tosylate anions were synthesized. Crystals of these compounds were grown in different crystal forms – solvent free and hydroquinone, benzene or ethyl acetate solvated ones. X-ray structural studies of the crystals shows that those containing tosylate and triiodide anions form the centrosymmetrically related stacking motif, typical for styryl dye cations and favorable for [2 + 2] photocycloaddition (PCA) reactions. This reaction takes place in crystals with tosylate anions as a single crystal-to-single crystal process. On the contrary, in the triiodide dye crystals, the PCA reaction is lacking, probably due to a weak directional interaction of the selenium atoms with the anions. The iodide dye crystals demonstrate non-typical packing for styryl dyes and manifest as a two-dimensional close packing motif of the cations which is unfavorable for cycloaddition.

Graphical abstract: Peculiarities of styryl dyes of the benzoselenazole series crystal packings and their influence on solid phase [2 + 2] photocycloaddition reaction with single crystal retention

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Publication details

The article was received on 23 Jun 2016, accepted on 21 Aug 2016 and first published on 22 Aug 2016


Article type: Paper
DOI: 10.1039/C6CE01426G
Citation: CrystEngComm, 2016,18, 7506-7515
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    Peculiarities of styryl dyes of the benzoselenazole series crystal packings and their influence on solid phase [2 + 2] photocycloaddition reaction with single crystal retention

    L. G. Kuz'mina, A. I. Vedernikov, J. A. K. Howard, S. I. Bezzubov, M. V. Alfimov and S. P. Gromov, CrystEngComm, 2016, 18, 7506
    DOI: 10.1039/C6CE01426G

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