Synthesis and Functionalization of Asymmetrical Benzo-Fused BODIPY Dyes

被引：103

作者：

Jiao, Lijuan ^{[1
]}

Yu, Changjiang

Liu, Mingming

Wu, Yangchun

Cong, Kebing

Meng, Ting

Wang, Yuqing

Hao, Erhong

机构：

[1] Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 17期

关键词：

FLUORESCENCE QUANTUM YIELDS; RESONANCE ENERGY-TRANSFER; RESTRICTED AZA-BODIPY; NEAR-INFRARED NIR; BORON-DIPYRROMETHENE; LIVING CELLS; DISTYRYL-BORADIAZAINDACENES; SPECTROSCOPIC PROPERTIES; HIGHLY FLUORESCENT; VISIBLE-LIGHT;

D O I：

10.1021/jo101164a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of asymmetrical benzo-fused BODIPY dyes were synthesized from the Sonogashira coupling and nucleophilic substitution reactions on the 3-halogenated benzo-fused BODIPY, generated from readily available 3-halogeno-1-formylisoindoles in a two-step synthetic procedure. This novel BODIPY platform provides an easy path for the linking of BODIPY fluorophore to various desired functionalities as demonstrated in this work. Most of the resulting BODIPY dyes show long-wavelength absorption and fluorescence emission, with good fluorescence quantum yields and long fluorescence lifetimes.

引用

收藏

页码：6035 / 6038

页数：4

相关论文

共 68 条

[1] A sensitive and selective ratiometric near IR fluorescent probe for zinc ions based on the distyryl-bodipy fluorophore [J].

Atilgan, Serdar ;

Ozdemir, Tugba ;

Akkaya, Engin U. .

ORGANIC LETTERS, 2008, 10 (18) :4065-4067

[2] Water soluble distyryl-boradiazaindacenes as efficient photosensitizers for photodynamic therapy [J].

Atilgan, Serdar ;

Ekmekci, Zeynep ;

Dogan, A. Lale ;

Guc, Dicle ;

Akkaya, Engin U. .

CHEMICAL COMMUNICATIONS, 2006, (42) :4398-4400

[3] A highly potassium-selective ratiometric fluorescent indicator based on BODIPY azacrown ether excitable with visible light [J].

Baruah, M ;

Qin, WW ;

Vallée, RAL ;

Beljonne, D ;

Rohand, T ;

Dehaen, W ;

Boens, N .

ORGANIC LETTERS, 2005, 7 (20) :4377-4380

[4] BODIPY-based hydroxyaryl derivatives as fluorescent pH probes [J].

Baruah, M ;

Qin, WW ;

Basaric, N ;

De Borggraeve, WM ;

Boens, N .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4152-4157

[5] Solvent and pH dependent fluorescent properties of a dimethylaminostyryl borondipyrromethene dye in solution [J].

Baruah, Mukulesh ;

Qin, Wenwu ;

Flors, Cristina ;

Hofkens, Johan ;

Valle, Renaud A. L. ;

Beljonne, David ;

Van der Auweraer, Mark ;

De Borggraeve, Wim M. ;

Boens, Noel .

JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (18) :5998-6009

[6] The use of site-directed fluorophore labeling and donor-donor energy migration to investigate solution structure and dynamics in proteins [J].

Bergström, F ;

Hägglöf, P ;

Karolin, J ;

Ny, T ;

Johansson, LBÅ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (22) :12477-12481

[7] Approaches to the stepwise synthesis of benzoporphyrins and phthalocyanines .1. Synthesis of opp-dibenzoporphyrins (dibenzo[g,q]porphyrins) [J].

Bonnett, R ;

McManus, KA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (20) :2461-2466

[8] Selective Manipulation of ICT and PET Processes in Styryl-Bodipy Derivatives: Applications in Molecular Logic and Fluorescence Sensing of Metal Ions [J].

Bozdemir, O. Altan ;

Guliyev, Ruslan ;

Buyukcakir, Onur ;

Selcuk, Sencer ;

Kolemen, Safacan ;

Gulseren, Gulcihan ;

Nalbantoglu, Tugrul ;

Boyaci, Hande ;

Akkaya, Engin U. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (23) :8029-8036

[9] Tetrastyryl-Bodipy Dyes: Convenient Synthesis and Characterization of Elusive Near IR Fluorophores [J].

Buyukcakir, Onur ;

Bozdemir, O. Altan ;

Kolemen, Safacan ;

Erbas, Sundus ;

Akkaya, Engin U. .

ORGANIC LETTERS, 2009, 11 (20) :4644-4647

[10] EFFECT OF SOLVENT POLARITY ON NONRADIATIVE PROCESSES IN XANTHENE DYES - RHODAMINE-B IN NORMAL ALCOHOLS [J].

CASEY, KG ;

QUITEVIS, EL .

JOURNAL OF PHYSICAL CHEMISTRY, 1988, 92 (23) :6590-6594

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