Highly-strained cyclophanes bearing both photo- and electro-active constituents
Highly-strained cyclophanes bearing both photo- and electro-active constituents
复制标题
DOI：
10.1016/j.tetlet.2011.08.013
复制
发表时间：
2011-10-12
影响因子：
1.8
通讯作者：
Harrington, Ross W.
中科院分区：
文献类型：
--
作者：
Benniston, Andrew C.;Harriman, Anthony;Harrington, Ross W.
通过偶氮苯甲酸与3，3 '-二羟基-4，4'-联吡啶在CH（2）Cl（2）中的偶联反应合成了一种含偶氮苯和甲基紫精单元的高张力环蕃。通过单晶X射线晶体学测定的分子结构表明，偶氮苯N=N单元采用反式构象，联吡啶单元是扭曲的。记录的目标化合物的循环伏安图显示在-0.37 V（相对于Ag/AgCl）处的不可逆波，与联吡啶亚基的单电子还原相关。在E（1/2）=-1.52V处观察到另一个波，相对于Ag/AgCl，并且被归因于偶氮苯基团的单电子还原。CH（3）CN中偶氮苯发色团的可见光照射引发反式到顺式异构化，但该过程是不可逆的。(C)2011爱思唯尔有限公司保留所有权利。
The synthesis of a highly-strained cyclophane comprising azobenzene and methyl viologen units was achieved by coupling 3,3'-dihydroxy-4,4'-bipyridine with azobenzoic acid in CH(2)Cl(2). The molecular structure, determined by single-crystal X-ray crystallography, shows that the azobenzene N=N unit adopts the trans conformation and that the bipyridinium unit is twisted. The cyclic voltammogram recorded for the target compound displays an irreversible wave at -0.37 V vs Ag/AgCl, associated with the one-electron reduction of the bipyridinium subunit. A further wave is seen at E(1/2) = -1.52 V versus Ag/AgCl and is assigned to one-electron reduction of the azobenzene group. Visible light illumination of the azobenzene chromophore in CH(3)CN triggers trans to cis isomerization but the process is irreversible. (C) 2011 Elsevier Ltd. All rights reserved.