A Water-Soluble pH-Triggered Molecular Switch

被引：68

作者：

Grunder, Sergio ^{[1
]}

McGrier, Psaras L. ^{[1
]}

Whalley, Adam C. ^{[1
]}

Boyle, Megan M. ^{[1
]}

Stern, Charlotte ^{[1
]}

Stoddart, J. Fraser ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 47期

基金：

美国国家科学基金会; 瑞士国家科学基金会;

关键词：

TEMPLATE-DIRECTED SYNTHESIS; POLYMER;

D O I：

10.1021/ja409006y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A bistable donor-acceptor [2]catenane, which is composed of a crown ether containing a hydroquinone unit and a 1,5-diaminonaphthalene unit, interlocked mechanically by cyclobis(paraquat-p-phenylene) as its tetrachloride, exists as a mixture of translational isomers, both in the solid state and in aqueous solution. UV/vis and H-1 NMR spectroscopies demonstrate that this isomeric mixture can be switched in water in the presence of hydrochloric acid to afford a single diprotonated derivative in which only the hydroquinone unit resides inside the cavity of the tetracationic cyclophane. Treatment with 1,4-diazabicyclo[2.2.2]octane resets the molecular switch.

引用

页码：17691 / 17694

页数：4

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