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Application of 2-Pyridyl-Substituted Hemithioindigo as a Molecular Switch in Hydrogen-Bonded Porphyrins.

  作者 Tanaka, Kiyoshi;Kohayakawa, Kiyoshi;Iwata, Satoru;Irie, Takayuki;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-10;  页码  3768-3774  
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[摘要]When the photochromism of (E)- and (Z)-2-(3'-pyridylmethylene)-7-ethylbenzo[b]thiophen-3(2H)-ones (I) was investigated, high thermal stability of the E isomer of I and good repeatability of the photoinduced E,Z-isomerization were found. Assocn. consts. of the 1:1 complexations of (Z)-I and (E)-I with the ureidoporphyrin II (R = NHEt) (III) and with the pentafluorobenzamidoporphyrin II (R = C6F5) (IV) were evaluated. We found that III captures (E)-I preferentially to (Z)-I and, reversely, IV prefers (Z)-I to (E)-I. 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 photoirradn. These movements were applied to create a mol. switch for changes in the quinone distribution between two kinds of porphyrins.

 
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