Synthesis of cesium selective pyridyl azocalix[n]arenes

被引：28

作者：

Chawla, HM ^{[1
]}

Singh, SP ^{[1
]}

Upreti, S ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, New Delhi 110016, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 12期

关键词：

calix[n]arenes; diazotization; cesium; hydrogen bond;

D O I：

10.1016/j.tet.2006.01.022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of pyridylazo calix[n]arenes (n=4, 6, 8) including the first examples of mixed hetroaryl azocalix(n)arene, have been synthesized by coupling calix[n]arenes with diazonium salts derived from amino pyridines. It has been observed that the coupling reaction of diazonium salt obtained from 3-aminopyridine with calix[n]arene gives tetrakis-, hexakis- and octakis (pyridylazo)calix[n]arenes (n=4,6 8) while those derived front 4-aminopyridine give partially substituted (4-pyridylazo)calix[n]arene analogs. There is no reaction of calix(n)arenes with diazonium salts derived from 2-aminopyridine under identical conditions of experiments. The conformational analysis of synthesized compounds have been ascertained by detailed spectral measurements and single crystal X-ray analysis of 5-(3'-pyridylazo)-25,26,27,28-tetrahydroxycalix[4]arene. A rational explanation for the observed partial and exhaustive coupling reaction in the synthesis of heteroaryl azocalix(n)arenes has been suggested. Preliminary evaluation of synthesized derivatives as molecular receptors for metal ions indicates that they have good potential to function as selective ionic filters for cesium ions. (c) 2006 Published by Elsevier Ltd.

引用

页码：2901 / 2911

页数：11

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