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

Asymmetric photoreaction of a diarylethene in hydrogen-bonded cocrystals with chiral molecules
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DOI:
10.1039/c3pp50239b
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发表时间:
2014-01-01
影响因子:
3.1
通讯作者:
Irie, Masahiro
Irie, Masahiro
中科院分区:
化学3区
文献类型:
--
作者:
Ichikawa, Tomohiro;Morimoto, Masakazu;Irie, Masahiro

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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 center dot center dot center dot 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.