Redox- and Protonation-Induced Fluorescence Switch in a New Triphenylamine with Six Stable Active or Non-Active Forms

被引:53
作者
Quinton, Cassandre [1 ]
Alain-Rizzo, Valerie [1 ]
Dumas-Verdes, Cecile [1 ]
Miomandre, Fabien [1 ]
Clavier, Gilles [1 ]
Audebert, Pierre [1 ]
机构
[1] ENS Cachan, CNRS UMR8531, PPSM, F-94235 Cachan, France
关键词
electrofluorochromism; fluorescence; molecular modeling; protonation; redox chemistry; triphenylamine; CATALYZED AMINATION; CONTRAST RATIO; BOND FORMATION; C-N; MICROSCOPY; ELECTROFLUOROCHROMISM; ELECTROCHEMISTRY; TRIARYLAMINES; MODULATION; SYSTEMS;
D O I
10.1002/chem.201404622
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis, photophysical and electrochemical properties as well as theoretical calculation studies of a newly designed triphenylamine derivative are described. This original compound displays one neutral form, three oxidized forms, and two protonated forms with distinct photo-physical characteristics. The interplay of the emission with the protonation or the redox state (electrofluorochromism) has been explored and an on-off-on-off fluorescence switching was observed in the case of oxidation and an on-on-off fluorescence switching in the case of protonation.
引用
收藏
页码:2230 / 2240
页数:11
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[1]   Coupling of electrochemistry and fluorescence microscopy at indium tin oxide microelectrodes for the analysis of single exocytotic events [J].
Amatore, C ;
Arbault, S ;
Chen, Y ;
Crozatier, C ;
Lemaître, F ;
Verchier, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :4000-4003
[2]  
Amatore C., 2006, ANGEW CHEM, V118, P4104
[3]   Electrofluorochromism: from molecular systems to set-up and display [J].
Audebert, P. ;
Miomandre, F. .
CHEMICAL SCIENCE, 2013, 4 (02) :575-584
[4]   Color Control in π-Conjugated Organic Polymers for Use in Electrochromic Devices [J].
Beaujuge, Pierre M. ;
Reynolds, John R. .
CHEMICAL REVIEWS, 2010, 110 (01) :268-320
[5]   Toward the development of new textile/plastic electrochromic cells using triphenylamine-based copolymers [J].
Beaupre, Serge ;
Dumas, Jean ;
Leclerc, Mario .
CHEMISTRY OF MATERIALS, 2006, 18 (17) :4011-4018
[6]   Electrofluorochromism in π-conjugated ionic liquid crystals [J].
Beneduci, Amerigo ;
Cospito, Sante ;
La Deda, Massimo ;
Veltri, Lucia ;
Chidichimo, Giuseppe .
NATURE COMMUNICATIONS, 2014, 5
[7]   Generation and Spectroscopic Profiles of Stable Multiarylaminium Radical Cations Bridged by Fluorenes [J].
Chang, Chao-Che ;
Yueh, Han ;
Chen, Chao-Tsen .
ORGANIC LETTERS, 2011, 13 (10) :2702-2705
[8]   Star-shaped conjugated systems derived from thienyl-derivatized poly(triphenylamine)s as active materials for electrochromic devices [J].
Cheng, Xinfeng ;
Zhao, Jinsheng ;
Cui, Chuansheng ;
Fu, Yunzhi ;
Zhang, Xianxi .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2012, 677 :24-30
[9]   Ethynylated Triphenylamine Monoboronic acid Chemosensors: Experimental and Theoretical Studies [J].
Chi, Lina ;
Wu, Yubo ;
Zhang, Xin ;
Ji, Shaomin ;
Shao, Jingyin ;
Guo, Huimin ;
Wang, Xin ;
Zhao, Jianzhang .
JOURNAL OF FLUORESCENCE, 2010, 20 (06) :1255-1265
[10]  
DEMAS JN, 1971, J PHYS CHEM-US, V75, P991, DOI 10.1021/j100678a001