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Asymmetric photoreaction of a diarylethene in hydrogen-bonded cocrystals with chiral molecules

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Abstract

A photochromic diarylethene having 2-methyl-4-pyridyl groups formed chiral cocrystals with (R)- or (S)-1,1′-bi-2-naphthol (BINOL). X-ray crystal structure analysis revealed that the diarylethene forms O–H⋯N type hydrogen bonds with BINOL and the central hexatriene moiety is fixed in P- or M-helix conformation in the cocrystals. The diarylethene molecules underwent reversible cyclization reactions in the single-component crystal as well as in the cocrystals upon alternate irradiation with ultraviolet (UV) and visible light. In the chiral cocrystals, a highly enantioselective photocyclization reaction took place owing to the conformational confinement.

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Authors and Affiliations

  1. Department of Chemistry and Research Center for Smart Molecules, Rikkyo University, 3-34-1 Nishi-Ikebukuro, Toshima-ku, Tokyo, 171-8501, Japan

    Tomohiro Ichikawa, Masakazu Morimoto & Masahiro Irie

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  1. Tomohiro Ichikawa
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  2. Masakazu Morimoto
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  3. Masahiro Irie
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Correspondence to Masahiro Irie.

Additional information

This article was submitted as part of a commemorative issue in honour of Nick Turro.

Electronic supplementary information (ESI) available: General methods, synthetic procedures, X-ray crystallography and spectroscopic data. CCDC 951471–951473. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3pp50239b

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Ichikawa, T., Morimoto, M. & Irie, M. Asymmetric photoreaction of a diarylethene in hydrogen-bonded cocrystals with chiral molecules. Photochem Photobiol Sci 13, 199–204 (2014). https://doi.org/10.1039/c3pp50239b

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  • DOI: https://doi.org/10.1039/c3pp50239b

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