Journal
SUPRAMOLECULAR CHEMISTRY
Volume 17, Issue 8, Pages 637-642Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10610270500148036
Keywords
benzoylhemithioindigo; molecular switch; ureidoporphyrin; quinone recognition
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The benzoyl-substituted hemithioindigo 1 with Z-configuration was obtained as the sole product from the reaction of 7-ethylbenzo[b]thiophen-3(2H)-one with phenylglyoxal. Irradiation of 1 produced the [2+4] cycloadduct 2, instead of the usual Z-E isomerization product. The cycloadduct 2 is completely dissociated back to 1 on heating; the interconversion between 1 and 2 shows good repeatability. This reversible property is applied to the molecular switch in the hydrogen-bonded quinone recognition of the 5,15-cis-bis(ureidophenyl)porphyrin 3.
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