A new terpyrrolic analogue of dipyrrolylquinoxalines: an efficient optical-based sensor for anions in organic media

被引：40

作者：

Shevchuk, SV ^{[1
]}

Lynch, VM ^{[1
]}

Sessler, JL ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Inst Cell & Mol Biol, Austin, TX 78712 USA

来源：

TETRAHEDRON | 2004年 / 60卷 / 49期

基金：

美国国家卫生研究院;

关键词：

anion sensors; pyrroles; molecular recognition;

D O I：

10.1016/j.tet.2004.08.054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and X-ray structural characterization of a new terpyrrolic analog of dipyrrolylquinoxaline (DPQ) is described that contains two pyrrole anion recognition groups bridged by a central 1,2-linked pyrrole. Relative to the 'parent' DPQ system, this new terpyrrolic scaffold acts as an improved colorimetric and fluorescent sensor for halide and dihydrogen phosphate anions in organic media. This enhancement is particularly dramatic in the case of H2PO (4) over bar (studied as its tetrabutylammonium salt); in CH2Cl2 it is bound with an affinity constant, K, of 17,500 M-1 by the terpyrrole of this report vs. 80 M-1 in the case of DPQ. The present findings thus support the emerging notion that a range of pyrrole-based anion recognition and sensing systems may be produced by replacing the central quinoxaline spacer in DPQs by other bridging subunits and that these new receptors may have properties that differ dramatically from their DPQ 'parents'. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：11283 / 11291

页数：9

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