Electrochromic and electrofluorochromic properties of a new boron dipyrromethene-ferrocene conjugate

被引:50
作者
Galangau, O. [1 ]
Fabre-Francke, I. [1 ]
Munteanu, S. [1 ]
Dumas-Verdes, C. [1 ]
Clavier, G. [1 ]
Meallet-Renault, R. [1 ]
Pansu, R. B. [1 ]
Hartl, F. [2 ]
Miomandre, F. [1 ]
机构
[1] Ecole Normale Super, PPSM, CNRS, UMR 8531, F-94235 Cachan, France
[2] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England
关键词
Boron dipyrromethene; Ferrocene; Electrochromic; Fluorescence; Redox switch; BODIPY DYES; SWITCH; TRIAD; UNITS; TETRATHIAFULVALENE; DERIVATIVES; CHEMISTRY;
D O I
10.1016/j.electacta.2012.09.048
中图分类号
O646 [电化学、电解、磁化学];
学科分类号
081704 ;
摘要
A new boron dipyrromethene-ferrocene (BODIPY-Fc) conjugate with pentafluorophenyl as the meso substituent and two Fc termini was synthesized and its spectroscopic and electrochemical features were analyzed. An intramolecular charge transfer from the donor Fc to the acceptor BODIPY has been predicted by theory and confirmed experimentally, leading to efficient fluorescence quenching when the dyad is in the neutral state. Fluorescence can be triggered by oxidizing both ferrocenyl units either chemically or electrochemically. Eventually, a fully reversible fluorescence switch is evidenced by coupling TIRF microscopy with electrolysis in an electrochemical cell. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:809 / 815
页数:7
相关论文
共 23 条
[1]  
[Anonymous], 2001, ELECTROCHEMICAL METH
[2]   Redox-controlled fluorescence modulation in a BODIPY-quinone dyad [J].
Benniston, Andrew C. ;
Copley, Graeme ;
Elliott, Kristopher J. ;
Harrington, Ross W. ;
Clegg, William .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (16) :2705-2713
[3]   Lighting the way ahead with boron dipyrromethene (Bodipy) dyes [J].
Benniston, Andrew C. ;
Copley, Graeme .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2009, 11 (21) :4124-4131
[4]   FERROCENE DERIVATIVES AS METALLOPROTEIN REDOX PROBES - ELECTRON-TRANSFER REACTIONS OF FERROCENE AND FERRICENIUM ION DERIVATIVES WITH CYTOCHROME-C [J].
CARNEY, MJ ;
LESNIAK, JS ;
LIKAR, MD ;
PLADZIEWICZ, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (09) :2565-2569
[5]   BODIPY-Tetrazine Multichromophoric Derivatives [J].
Dumas-Verdes, Cecile ;
Miomandre, Fabien ;
Lepicier, Eve ;
Galangau, Olivier ;
Vu, Thanh Truc ;
Clavier, Gilles ;
Meallet-Renault, Rachel ;
Audebert, Pierre .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (13) :2525-2535
[6]  
Frisch M. J., 2004, GAUSSIAN 03
[7]   Rational design of visible and NIR distyryl-BODIPY dyes from a novel fluorinated platform [J].
Galangau, Olivier ;
Dumas-Verdes, Cecile ;
Meallet-Renault, Rachel ;
Clavier, Gilles .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4546-4553
[8]   VERSATILE CRYOSTATED OPTICALLY TRANSPARENT THIN-LAYER ELECTROCHEMICAL (OTTLE) CELL FOR VARIABLE-TEMPERATURE UV-VIS IR SPECTROELECTROCHEMICAL STUDIES [J].
HARTL, F ;
LUYTEN, H ;
NIEUWENHUIS, HA ;
SCHOEMAKER, GC .
APPLIED SPECTROSCOPY, 1994, 48 (12) :1522-1528
[9]   A novel all-organic chemical and electrochemical fluorescent switch [J].
Illos, RA ;
Harlev, E ;
Bittner, S .
TETRAHEDRON LETTERS, 2005, 46 (48) :8427-8430
[10]   Synthesis and studies of covalently linked meso-furyl boron-dipyrromethene-ferrocene conjugates [J].
Khan, Tamanna K. ;
Pissurlenkar, Raghuvir R. S. ;
Shaikh, Mushtaque S. ;
Ravikanth, M. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 697 (01) :65-73