New insights into the solubilization of Bodipy dyes

被引：52

作者：

Niu, Song-Lin ^{[1
]}

Ulrich, Gilles ^{[1
]}

Retailleau, Pascal ^{[2
]}

Harrowfield, Jack ^{[3
]}

Ziessel, Raymond ^{[1
]}

机构：

[1] LCOSA, F-67087 Strasbourg, France

[2] CNRS, ICSN, Cristallochim Lab, F-91198 Gif Sur Yvette, France

[3] ISIS, F-67083 Strasbourg, France

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 27期

关键词：

Bodipy; Pyrene; Sulfobetaine; Water solubility; Fluorescence; ENERGY-TRANSFER; ELECTROGENERATED CHEMILUMINESCENCE; LASER-DYES; CHEMISTRY; FLUORESCENCE; BORON; FUNCTIONALIZATION; DERIVATIVES; DEVICES; SENSOR;

D O I：

10.1016/j.tetlet.2009.04.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several Bodipy dyes were synthesized with various substituents designed to improve the water solubility. Among the different synthetic strategies protection of sulfonate groups by pyrrole of indopyrrole appears efficient but the deprotection step does not offer viable routes. Conversion of the bromopyrene or iodo Bodipy compounds to sulfobetaine derivatives is feasible either by cross-coupling directly the ethynyl-sulfobetaine or by first cross-coupling 1-(N,N-dimethylamino)-prop-2-yne followed by quaternization of the dimethylamino residue with 1,3-propanesultone. Some of these dyes (Bodipy's and pyrene) are reasonably soluble in water and remain highly fluorescent in polar solvents and water. (c) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3840 / 3844

页数：5

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