A 'building block' approach to functionalized calix[4]pyrroles

被引：82

作者：

Miyaji, H

Sato, W

Sessler, JL ^{[1
]}

Lynch, VM

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

[2] Univ Texas, Inst Cellular & Mol Biol, Austin, TX 78712 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 09期

基金：

美国国家卫生研究院;

关键词：

calix[4]pyrrole; iodination; Sonogashira coupling; anion sensor;

D O I：

10.1016/S0040-4039(99)02295-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iodocalix[4]pyrrole 2 and trimethylsilylethynyicalix[4]pyrrole 3 are key intermediates en route to the preparation of the alkynyl-substituted calix[4]pyrrole system 4. This latter species, in turn, provides a versatile precursor that can be used to prepare a range of arylalkynyl-functionalized calix[4]pyrroles (viz., 5-9) by reacting with an appropriate aryl iodide under Sonogashira conditions (i.e., in the presence of tetrakis (triphenylphosphine)palladium(0)). Significant red-shifts in the lambda(max) values and broadenings of the absorption peaks are seen in the UV-vis spectra of systems 6 and 7 upon addition of anions (e.g., F-, Cl-, H2PO4-) in CH2Cl2, a finding that leads to the suggestion that these or other analogous systems could find application as anion sensors. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1369 / 1373

页数：5

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