基于带有蒽基的联萘分子的手性分子开关：发色团间激子耦合导致的圆二色信号及圆二色光谱的调制。

Chiral molecular switches based on binaphthalene molecules with anthracene moieties: CD signal due to interchromophoric exciton coupling and modulation of the CD spectrum.

作者信息

Wang Cheng, Zhu Lingyun, Xiang Junfeng, Yu Yanxin, Zhang Deqing, Shuai Zhigang, Zhu Daoben

机构信息

Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.

出版信息

J Org Chem. 2007 Jun 8;72(12):4306-12. doi: 10.1021/jo070044r. Epub 2007 May 12.

DOI:10.1021/jo070044r

PMID:17497922

Abstract

By coupling the features of binaphthalene and anthracene, new binaphthalenes with two anthracene moieties were designed and synthesized, aiming at developing chiral molecular switches. A strong CD signal with negative sign due to the interchromophoric exciton coupling was observed for (S)-1 with -(CH2)2 as the linker. This new CD signal became weak and the sign reversed by changing the linker to -(CH2)3 in (S)-2 and -(CH2)6 in (S)-3. For (S)-4 with -(CH2)11 as the linker, no such CD signal was detected. Photodimerization of two anthracene moieties in these binaphthalene molecules can occur. The results show that the CD spectra of (S)-1, (S)-2, (S)-3, and (R)-1 can be reversibly modulated by alternating UV light irradiation and heating. Therefore, chiral molecular switches based on new binaphthalenes with two anthracene moieties are achieved.

摘要

通过结合联萘和蒽的特性，设计并合成了带有两个蒽部分的新型联萘，旨在开发手性分子开关。对于以-(CH2)2作为连接基团的(S)-1，由于发色团间的激子耦合，观察到一个强烈的负号圆二色信号。通过将连接基团分别改为(S)-2中的-(CH2)3和(S)-3中的-(CH2)6，这个新的圆二色信号变弱且符号反转。对于以-(CH2)11作为连接基团的(S)-4，未检测到此类圆二色信号。这些联萘分子中的两个蒽部分会发生光二聚反应。结果表明，通过交替进行紫外光照射和加热，(S)-1、(S)-2、(S)-3和(R)-1的圆二色光谱可以被可逆地调制。因此，实现了基于带有两个蒽部分的新型联萘的手性分子开关。