Near-infrared BODIPY dyes modulated with spirofluorene moieties

被引：23

作者：

Kowada, Toshiyuki ^{[1
]}

Yamaguchi, Shuhei ^{[1
]}

Fujinaga, Hiroki ^{[1
]}

Ohe, Kouichi ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Nishikyo Ku, Kyoto 6158510, Japan

来源：

TETRAHEDRON | 2011年 / 67卷 / 17期

基金：

日本学术振兴会;

关键词：

BODIPY dye; Fluorescence; Near-infrared; C-H arylation; Charge transfer; RESONANCE ENERGY-TRANSFER; RESTRICTED AZA-BODIPY; HIGHLY FLUORESCENT; DIRECT ARYLATION; DERIVATIVES; BORON; CHEMOSENSOR; EMISSION; DESIGN; ION;

D O I：

10.1016/j.tet.2011.02.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New structurally constrained BODIPY dyes having electron-donating substituents were synthesized. As the key compounds for the construction of the BODIPY dyes, 1'H-spiro-[fluorene-9,4'-indeno[1,2-b] pyrrole] (sp-FIP) derivatives with electron-donating groups, such as OMe and NMe2 at its 6'-position, were prepared using palladium-catalyzed intramolecular direct C-H arylation of a pyrrole moiety. The resulting BODIPY dyes showed bathochromic shift in absorption and fluorescence spectra in comparison to the unsubstituted analogs. Furthermore, pH-dependent reversible spectrum changes of the BODIPY dye were observed with the addition of trifluoroacetic acid (TFA) and subsequent addition of i-Pr2NEt. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3105 / 3110

页数：6

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