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Tanaka K, Kohayakawa K, Iwata S, et al. Application of 2-pyridyl-substituted hemithioindigo as a molecular switch in hydrogen-bonded porphyrins. J Org Chem. 2008;73(10):3768-74doi: 10.1021/jo800091d.
Tanaka, K., Kohayakawa, K., Iwata, S., & Irie, T. (2008). Application of 2-pyridyl-substituted hemithioindigo as a molecular switch in hydrogen-bonded porphyrins. The Journal of organic chemistry, 73(10), 3768-74. https://doi.org/10.1021/jo800091d
Tanaka, Kiyoshi, et al. "Application of 2-pyridyl-substituted hemithioindigo as a molecular switch in hydrogen-bonded porphyrins." The Journal of organic chemistry vol. 73,10 (2008): 3768-74. doi: https://doi.org/10.1021/jo800091d
Tanaka K, Kohayakawa K, Iwata S, Irie T. Application of 2-pyridyl-substituted hemithioindigo as a molecular switch in hydrogen-bonded porphyrins. J Org Chem. 2008 May 16;73(10):3768-74. doi: 10.1021/jo800091d. Epub 2008 Apr 23. PMID: 18429634.
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J Org Chem. 2008 May 16;73(10):3768-74. doi: 10.1021/jo800091d. Epub 2008 Apr 23.

Application of 2-pyridyl-substituted hemithioindigo as a molecular switch in hydrogen-bonded porphyrins.

The Journal of organic chemistry

Kiyoshi Tanaka, Kiyoshi Kohayakawa, Satoru Iwata, Takayuki Irie

Affiliations

  1. Laboratory of Molecular Control, Faculty of Science and Technology, Seikei University, Musashino-Shi, Tokyo, Japan. [email protected]

PMID: 18429634 DOI: 10.1021/jo800091d

Abstract

When the photochromism of 2-(3'-pyridylmethylene)-7-ethylbenzo[b]thiophen-3(2H)-ones (4) was investigated, high thermal stability of the E isomer of 4, 4(E) and good repeatability of the photoinduced E,Z-isomerization were found. Association constants of the 1:1 complexations of 4(Z) and 4(E) with the ureidoporphyrin 1 and with the pentafluorobenzamidoporphyrin 2 were evaluated. We found that 1 captures 4(E) preferentially to 4(Z) and, reversely, 2 prefers 4(Z) to 4(E). On the basis of these differences in the binding ability, we concluded that the repeatable movement of the hemithioindigo, so-called the hemithioindigo shuttle, between two kinds of porphyrins was controlled by the photoirradiation. These movements were applied to create a molecular switch for changes in the quinone distribution between two kinds of porphyrins.

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