PHOTORESOLUTION OF AN AXIALLY CHIRAL BICYCLO[3.2.1]OCTAN-3-ONE - PHOTOTRIGGERS FOR A LIQUID CRYSTAL-BASED OPTICAL SWITCH

被引：55

作者：

ZHANG, YF ^{[1
]}

SCHUSTER, GB ^{[1
]}

机构：

[1] UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 22期

关键词：

D O I：

10.1021/jo00127a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The axially chiral ketones 8-(phenylmethylene)bicyclo[3.2.1]octan-3-one (1) and 3-(phenylmethylene)bicyclo[3.2,1]octan-8-one (2) were prepared and investigated for suitability as a chiroptical trigger in a liquid crystal-based optical switch. Irradiation of optically active ketone 1 with unpolarized light leads to its efficient photoracemization. Its irradiation with circularly polarized light leads to partial photoresolution with an enantiomeric excess sufficient for it to function as a chiroptical trigger. However, 1 is not sufficiently soluble in ZLI-1167, a nematic liquid crystalline material, to induce a measurable pitch. Ketone 2 is unstable to irradiation and is not suitable for use as a chiroptical trigger.

引用

页码：7192 / 7197

页数：6

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