Original electroactive and fluorescent bichromophores based on non-conjugated tetrazine and triphenylamine derivatives: towards more efficient fluorescent switches

作者: Cassandre Quinton , Valérie Alain-Rizzo , Cécile Dumas-Verdes , Gilles Clavier , Pierre Audebert

DOI: 10.1039/C5RA07253K

关键词:

摘要: The synthesis, photophysical and electrochemical properties their interplay as well theoretical calculations studies of newly designed fluorescent electroactive derivatives are described. These molecules composed two fluorophores: one triphenylamine, electron-rich unit, tetrazine, electron-poor connected by different links. While in the neutral state bichromophores not fluorescent, due to a photoinduced electron transfer from triphenylamine unit tetrazine fluorescence is restored oxidative (oxidation moiety).

参考文章(45)
Glenn A. Crosby, James N. Demas, Measurement of photoluminescence quantum yields. Review The Journal of Physical Chemistry. ,vol. 75, pp. 991- 1024 ,(1971) , 10.1021/J100678A001
Hai Guang Zhang, Xu Tang Tao, Kao Shan Chen, Chun Xue Yuan, Shi Na Yan, Min Hua Jiang, Off–on–off luminescent switching of a dye containing imidazo[4, 5-f][1, 10]phenanthroline Chinese Chemical Letters. ,vol. 22, pp. 647- 650 ,(2011) , 10.1016/J.CCLET.2010.12.005
Cassandre Quinton, Valérie Alain-Rizzo, Cécile Dumas-Verdes, Fabien Miomandre, Gilles Clavier, Pierre Audebert, Redox-controlled fluorescence modulation (electrofluorochromism) in triphenylamine derivatives RSC Advances. ,vol. 4, pp. 34332- 34342 ,(2014) , 10.1039/C4RA02675F
Norio. Miyaura, Akira. Suzuki, Palladium-catalyzed cross-coupling reactions of organoboron compounds Chemical Reviews. ,vol. 95, pp. 2457- 2483 ,(1995) , 10.1021/CR00039A007
Kesavapillai Sreenath, Chettiyam Veettil Suneesh, Karical R Gopidas, Robert A Flowers, None, Generation of Triarylamine Radical Cations through Reaction of Triarylamines with Cu(II) in Acetonitrile. A Kinetic Investigation of the Electron-Transfer Reaction Journal of Physical Chemistry A. ,vol. 113, pp. 6477- 6483 ,(2009) , 10.1021/JP9027222
Cassandre Quinton, Valérie Alain-Rizzo, Cécile Dumas-Verdes, Fabien Miomandre, Pierre Audebert, Tetrazine–triphenylamine dyads: Influence of the nature of the linker on their properties Electrochimica Acta. ,vol. 110, pp. 693- 701 ,(2013) , 10.1016/J.ELECTACTA.2013.02.113
Daniele Simoni, Francesco Paolo Invidiata, Marco Eleopra, Paolo Marchetti, Riccardo Rondanin, Riccardo Baruchello, Giuseppina Grisolia, Ashutosh Tripathi, Glen E. Kellogg, David Durrant, Ray M. Lee, Design, synthesis and biological evaluation of novel stilbene-based antitumor agents. Bioorganic & Medicinal Chemistry. ,vol. 17, pp. 512- 522 ,(2009) , 10.1016/J.BMC.2008.12.002
Stephen Barlow, Chad Risko, Susan A. Odom, Shijun Zheng, Veaceslav Coropceanu, Luca Beverina, Jean-Luc Brédas, Seth R. Marder, Tuning Delocalization in the Radical Cations of 1,4-Bis[4-(diarylamino)styryl]benzenes, 2,5-Bis[4-(diarylamino)styryl]thiophenes, and 2,5-Bis[4-(diarylamino)styryl]pyrroles through Substituent Effects Journal of the American Chemical Society. ,vol. 134, pp. 10146- 10155 ,(2012) , 10.1021/JA3023048
Yuna Kim, Jaekwon Do, Eunkyoung Kim, Gilles Clavier, Laurent Galmiche, Pierre Audebert, Tetrazine-based electrofluorochromic windows: Modulation of the fluorescence through applied potential Journal of Electroanalytical Chemistry. ,vol. 632, pp. 201- 205 ,(2009) , 10.1016/J.JELECHEM.2008.07.022
Gilles Clavier, Pierre Audebert, s-Tetrazines as Building Blocks for New Functional Molecules and Molecular Materials Chemical Reviews. ,vol. 110, pp. 3299- 3314 ,(2010) , 10.1021/CR900357E