Design, synthesis and redox properties of a fluorene platform linking two different Bodipy dyes

被引:31
作者
Bura, Thomas [1 ]
Ziessel, Raymond [1 ]
机构
[1] ECPM, LCOSA, F-67087 Strasbourg, France
关键词
Bodipys'; Fluorene; Bipyridine; Styryl; Formylation; Electrochemistry; LINKED MULTIPORPHYRIN ARRAYS; BORON-DIPYRROMETHENE DYES; SENSITIZED SOLAR-CELLS; ENERGY-TRANSFER; COMPLEXES; CHEMISTRY; FLUORESCENCE; DEVICES; SENSOR; DYADS;
D O I
10.1016/j.tetlet.2010.03.095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several new fluorophores have been prepared by grafting boradiazaindacene (red absorbing) and/or styrylboradiazaindacene (blue absorbing) units as terminal energy acceptors onto a fluorene-derived platform. In one case, an amino-bis(bipyridine) pocket has been attached to enable strong binding of transition metal ions. The stepwise syntheses were largely based on Pd-catalysed cross-coupling reactions. The electrochemistry of the dyes has been analysed by reference to the properties of the various synthetic intermediates, protonation of the tertiary amine site present in the bis(bipyridine) species enabling processes involving this centre to be distinguished from those associated with the boradiazaindacene (Bodipy) unit. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2875 / 2879
页数:5
相关论文
共 38 条
[1]  
[Anonymous], 2002, Molecular Mechanisms of Photosynthesis
[2]   Intramolecular charge transfer in pyrromethene laser dyes:: Photophysical behaviour of PM650 [J].
Arbeloa, FL ;
Prieto, JB ;
Martínez, VM ;
López, TA ;
Arbeloa, IL .
CHEMPHYSCHEM, 2004, 5 (11) :1762-1771
[3]   Tailoring the properties of boron-dipyrromethene dyes with acetylenic functions at the 2,6,8 and 4-B substitution positions [J].
Bonardi, Laure ;
Ulrich, Gilles ;
Ziessel, Raymond .
ORGANIC LETTERS, 2008, 10 (11) :2183-2186
[4]   Highly luminescent gels and mesogens based on elaborated borondipyrromethenes [J].
Camerel, F ;
Bonardi, L ;
Schmutz, M ;
Ziessel, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) :4548-4549
[5]   Self-assembly of fluorescent amphipathic borondipyrromethene scaffoldings in mesophases and organogels [J].
Camerel, Franck ;
Bonardi, Laure ;
Ulrich, Gilles ;
Charbonniere, Loic ;
Donnio, Bertrand ;
Bourgogne, Cyril ;
Guillon, Daniel ;
Retailleau, Pascal ;
Ziessel, Raymond .
CHEMISTRY OF MATERIALS, 2006, 18 (21) :5009-5021
[6]   Signal ratio amplification via modulation of resonance energy transfer: Proof of principle in an emission ratiometric Hg(II) sensor [J].
Coskun, Ali ;
Akkaya, Engin U. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (45) :14474-14475
[7]  
DEMENDOZA J, 1991, ANGEW CHEM INT EDIT, V30, P1331, DOI 10.1002/anie.199113311
[8]   Improved push-pull-push E-Bodipy fluorophores for two-photon cell-imaging [J].
Didier, Pascal ;
Ulrich, Gilles ;
Mely, Yves ;
Ziessel, Raymond .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (18) :3639-3642
[9]   Star-Shaped Multichromophoric Arrays from Bodipy Dyes Grafted on Truxene Core [J].
Diring, Stephane ;
Puntoriero, Fausto ;
Nastasi, Francesco ;
Campagna, Sebastiano ;
Ziessel, Raymond .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) :6108-+
[10]   A panchromatic boradiazaindacene (BODIPY) sensitizer for dye-sensitized solar cells [J].
Erten-Ela, Sule ;
Yilmaz, M. Deniz ;
Icli, Burcak ;
Dede, Yavuz ;
Icli, Siddik ;
Akkaya, Engin U. .
ORGANIC LETTERS, 2008, 10 (15) :3299-3302