Diastereoselective photochromism of an (R)-binaphthol-condensed indolylfulgide
Diastereoselective photochromism of an (R)-binaphthol-condensed indolylfulgide
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DOI：
10.1021/ja9523045
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发表时间：
1996-04-03
影响因子：
15
通讯作者：
Kurita, Y
中科院分区：
文献类型：
--
作者：
Yokoyama, Y;Uchida, S;Kurita, Y
合成了两种新的热不可逆光致变色（R）-联萘酚缩吲哚俘精酸酐（分别含1-（1，2-二甲基-3-吲哚基）-2-甲基丙叉基和1-（1，2-二甲基-3-吲哚基）丁叉基，6和7）。由于在室温下7 E的构象异构体之间的快速热平衡，大部分7 E通过（P）-7E α发生光环化，选择性地得到（9aS）-6C。另一方面，由于6 E在室温下的热平衡需要很长时间，因此其光致变色互变仅发生在（P）-6E α和（9aS）-6C之间，并且光环化惰性6 E保持不变。在俘精酸酐类化合物中，7的热稳定性和抗疲劳性都很好。光致变色反应伴随着大的比旋光度值的变化。对可见光敏感的有色形式（9aS）-6C进行了X射线晶体学分析。
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)-7E alpha to give (9aS)-6C selectively. On the other hand, as thermal equilibration requires a long time for 6E at room temperature, its photochromic interconversion occurs only between (P)-6E alpha 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.