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

作者：Tanaka Kiyoshi^*; Kohayakawa Kiyoshi; Iwata Satoru; Irie Takayuki

来源：Journal of Organic Chemistry, 2008, 73(10): 3768-3774.

DOI：10.1021/jo800091d

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 I 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.

• 出版日期2008-5-16