Application of Benzoyl-substituted Hemithioindigo as a Molecular Switch in Porphyrin-Quinone Recognition |
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| Authors: | Kiyoshi Tanaka Kazuto Taguchi Satoru Iwata Takayuki Irie |
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| Affiliation: | 1. Seikei University, Laboratory of Molecular Control, Faculty of Science and Technology , Musashino-shi, Tokyo, Japan tanaka@st.seikei.ac.jp;3. Seikei University, Laboratory of Molecular Control, Faculty of Science and Technology , Musashino-shi, Tokyo, Japan |
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| Abstract: | 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. resulting in the release of |
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| Keywords: | Benzoylhemithioindigo Molecular switch Ureidoporphyrin Quinone recognition |
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