Tuning the anion binding properties of calixpyrroles by means of p-nitrophenyl substituents at their meso-positions

被引：51

作者：

Bruno, Giuseppe ^{[2
]}

Cafeo, Grazia ^{[1
]}

Kohnke, Franz H. ^{[1
]}

Nicolo, Francesco ^{[2
]}

机构：

[1] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy

[2] Univ Messina, Dipartimento Chim Inorgan & Chim Fis, I-98166 Messina, Italy

来源：

TETRAHEDRON | 2007年 / 63卷 / 40期

关键词：

extended calixpyrrole; anions; receptors; complexation;

D O I：

10.1016/j.tet.2007.07.060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Extended cavity calix[4]pyrroles and a calix[6]pyrrole were synthesized by cyclization of 5-methyl-5-(4-nitrophenyl)dipyrromethane with acetone in the presence of acid. The solid-state structures of the novel macrocycles were determined by X-ray crystallography. The host-guest chemistry of these receptors towards halide ions was investigated in solution by H-1 NMR titration techniques and compared with those of the meso-octamethylcalix[4]pyrrole and meso-dodecamethylcalix[6]pyrrole. The binding of chloride anions was observed to occur with different affinities on the two faces of the novel calix[6]pyrrole derivative described here. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：10003 / 10010

页数：8

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