A 'clicked' macrocyclic probe incorporating Binol as the signalling unit for the chiroptical sensing of anions

被引：70

作者：

Caricato, Marco ^{[1
,2
]}

Olmo, Alessandro ^{[1
,2
]}

Gargiulli, Claudia ^{[3
]}

Gattuso, Giuseppe ^{[3
]}

Pasini, Dario ^{[1
,2
]}

机构：

[1] Univ Pavia, Dept Chem, I-27100 Pavia, Italy

[2] Univ Pavia, INSTM Res Unit, I-27100 Pavia, Italy

[3] Univ Messina, Dept Organ & Biol Chem, I-98166 Messina, Italy

来源：

TETRAHEDRON | 2012年 / 68卷 / 38期

关键词：

Circular dichroism; Macrocycles; Click chemistry; Anion binding; Sensors; BUILDING-BLOCKS; RECOGNITION; METAL; CYCLOPHANE; RECEPTORS; PORPHYRIN; CHEMISTRY; INVERSION; PROGRAM; DESIGN;

D O I：

10.1016/j.tet.2012.07.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a macrocyclic chiroptical sensor for the detection of halide anions, with the Binol moiety acting as the CD signalling unit. The macrocycle is conveniently synthesized using CuAAC 'click' reactions in the cyclization step; this methodology installs 1,2,3-triazole moieties within the macrocyclic backbone, able to directionally bind anions by means of CH center dot center dot center dot X- hydrogen bonds. H-1 NMR complexation studies in CDCl3 reveal weak binding to halide and aliphatic carboxylate anions. Halide anions, however, when held into the macrocyclic cavity, are able to trigger a large chiroptical response originating from the steric interaction with the Binol moiety, which changes its dihedral angle, thus modulating its characteristic CD signature. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：7861 / 7866

页数：6

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