American Chemical Society
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Diastereoselective Photochromism of an (R)-Binaphthol-Condensed Indolylfulgide

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journal contribution
posted on 1996-04-03, 00:00 authored by Yasushi Yokoyama, Soichi Uchida, Yayoi Yokoyama, Yoko Sugawara, Yukio Kurita
Two new thermally irreversible photochromic (R)-binaphthol-condensed indolylfulgides (with a 1-(1,2-dimethyl-3-indolyl)-2-methylpropylidene group and with a 1-(1,2-dimethyl-3-indolyl)butylidene group, 6 and 7, respectively) were synthesized. Because of rapid thermal equilibration between the conformational isomers of 7E at room temperature, photocyclization of a substantial portion of 7E occurred through (P)-7Eα to give (9aS)-7C selectively. On the other hand, as thermal equilibration requires a long time for 6E at room temperature, its photochromic interconversion occurs only between (P)-6Eα and (9aS)-6C, and the photocyclization-inert 6E remained unchanged. The thermal stability and fatigue resistivity toward the iterative photochromic interconversion of 7 have been proved to be excellent among the fulgide derivatives. The photochromic reactions were accompanied by large changes of specific rotation values. The X-ray crystallographic analysis of a visible-light-sensitive colored form, (9aS)-6C, was carried out.