Synthesis and Optical Properties of 2-(Benzo[b]thiophene-3-yl)pyrroles and a New BODIPY Fluorophore (BODIPY=4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene)

被引：44

作者：

Schmidt, Elena Yu ^{[1
]}

Trofimov, Boris A. ^{[1
]}

Mikhaleva, Al'bina I. ^{[1
]}

Zorina, Nadezhda V. ^{[1
]}

Protzuk, Nadezhda I. ^{[1
]}

Petrushenko, Konstantin B. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

Dvorko, Marina Yu ^{[1
]}

Meallet-Renault, Rachel ^{[2
]}

Clavier, Gilles ^{[2
]}

Vu, Thanh Truc ^{[2
]}

Tran, Ha Thanh Thao ^{[2
]}

Pansu, Robert B. ^{[2
]}

机构：

[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia

[2] UniverSud, ENS Cachan, PPSM, CNRS, F-94230 Cachan, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 23期

基金：

俄罗斯基础研究基金会;

关键词：

acetylene; chromophores; fluorescence; pyrroles; ENERGY-TRANSFER; DYES; FLUORESCENCE; DERIVATIVES; CHEMISTRY; PYRROLE;

D O I：

10.1002/chem.200802467

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-(Benzo[b]thiophene-3-yl)-1-vinylpyrrole has been synthesized directly from 3-acetylbenzo[b]thiophene oxime and acetylene (flow system, KOH-DMSO, 120 degrees C, 5h) in 68% yield. Devinylation of the synthesized pyrrole (Hg(OAc)(2), NaBH4, 50 degrees C) led to the corresponding 2-(benzo[b]thiophene-3-yl)pyrrole in 63% yield. Trifluoroacetylation of both the pyrroles with influoroacetic anhydride (80 degrees C, 1 h) gave the corresponding 5-trifluoroacetyl pyrroles in 97% and 76% yields, respectively. 2-(Benzo[b]thiophene-3-yl)pyrrole was reacted subsequently with mesityl aldehyde, 2,3-dichloro-5,6-dicyano-1-4-benzoquinone (DDQ), and BF3 center dot OEt2 to afford 4,4-difluoro-3,5-di(benzo[b]thiophene-3-yl)-8-mesityl-4-bora-3a,4a-diaza-s-indacene, a representative of the novel BODIPY fluorophore family (BODIPY = 4,4-dinuoro-4-bora-3a,4a-diaza-s-indacene), in 34% overall yield. The synthesized pyrroles exhibit promising optical properties (absorption and emission spectra, nonlinear optical (NLO) features), superior to existing analogues. The BODIPY fluorophore displays an intense red-shifted fluorescence emission in CH2Cl2 (625 nm, 0.84 fluorescence quantum yield) that is fully preserved in the solid state.

引用

页码：5823 / 5830

页数：8

共 47 条

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