Pyrrolopyrrole Cyanine Dyes: A New Class of Near-Infrared Dyes and Fluorophores

被引：126

作者：

Fischer, Georg M. ^{[1
]}

Isomaeki-Krondahl, Magnus ^{[1
]}

Goettker-Schnetmann, Inigo ^{[1
]}

Daltrozzo, Ewald ^{[1
]}

Zumbusch, Andreas ^{[1
]}

机构：

[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 19期

关键词：

chromophores; dyes/pigments; fluorescent probes; fluorophores; heterocycles; RESTRICTED AZA-BODIPY; HIGHLY FLUORESCENT; BRIGHT; BORON;

D O I：

10.1002/chem.200801996

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pyrrolopyrrole cyanine (PPCy) dyes are presented as a novel class of near-infrared (NIR) chromophores, which are synthesized in a condensation reaction of diketopyrrolopyrrole with heteroarylacetonitrile compounds. Their optical properties are marked by strong and narrow-band NIR absorptions. Complexation products with BF2 and BPh2 show strong NIR fluorescence and hardly any absorption in the visible range. We synthesized a series of new PPCys that differ only in the heterocyclic peripheral groups of the chromophore. With this strategy, the absorption spectra can be tuned between 684 and 864 nm, while high fluorescence quantum yields are maintained. The influence of the heterocycle on the optical properties of the dyes is discussed.

引用

页码：4857 / 4864

页数：8

共 37 条

[1]

ABEL EW, 1956, J CHEM SOC, P4697

[2] 2,5-DIAZAPENTALENES [J].

CLOSS, F ;

GOMPPER, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (06) :552-554

[3]

Closs F., 1987, ANGEW CHEM, V99, P566

[4] MOLECULAR ENGINEERING OF CYANINE-TYPE FLUORESCENT AND LASER-DYES [J].

CZERNEY, P ;

GRANESS, G ;

BIRCKNER, E ;

VOLLMER, F ;

RETTIG, W .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1995, 89 (01) :31-36

[5]

DAHNE S, 1998, NATO 3, V52, P61905

[6]

DALTROZZO E, 2003, Patent No. 1054039

[7]

DALTROZZO E, 1992, Patent No. 0217245

[8] Phenanthrene-fused boron-dipyrromethenes as bright long-wavelength fluorophores [J].

Descalzo, Ana B. ;

Xu, Hai-Jun ;

Xue, Zhao-Li ;

Hoffmann, Katrin ;

Shen, Zhen ;

Weller, Michael G. ;

You, Xiao-Zeng ;

Rurack, Knut .

ORGANIC LETTERS, 2008, 10 (08) :1581-1584

[9] POLYMETHINE DYES WITH LIGHT-ABSORPTION IN THE NEAR-INFRARED [J].

FABIAN, J .

JOURNAL FUR PRAKTISCHE CHEMIE, 1991, 333 (02) :197-222

[10]

Fischer G.M., 2007, ANGEW CHEMIE, V119, P3824

← 1 2 3 4 →