Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 32, Pages 9463-9467Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705325
Keywords
[2+2] cycloaddition; dynamic molecular crystals; photomechanical effect; styrylbenzoxazole; topo-photochemical reactions
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Funding
- National Natural Science Foundation of China [21374041, 21503090]
- Open Project of State Key Laboratory of Supramolecular Structure and Materials [SKLSSM201717]
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We report interesting photomechanical behaviors of the dynamic molecular crystals of (E)-2-(2,4-dichlorostyryl)benzo[d]oxazole (BOACl24). The photosalient effect of the rod-like crystal based on a metal-free olefin driven by photodimerization is observed. Moreover, the needle-like crystals of BOACl24 exhibit a reversible bending away from a UV light source. The nanofibers curl easily under UV irradiation in an organogel, in which the photo-induced rolling of a small slice occurs. This suggests that the rapid release of the accumulated strain during photodimerization may lead to a photosalient effect, and the bending or curling happens when the strain is released slowly. Notably, [2+2] cycloaddition takes place between two different conformational isomers of BOACl24 on account of the rotation of the benzoxazole ring around the C-C bond in an excited state before photodimerization. Such topo-photochemical reaction has not been reported elsewhere.
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