Synthesis of Symmetrical Multichromophoric Bodipy Dyes and Their Facile Transformation into Energy Transfer Cassettes

被引:67
作者
Bozdemir, O. Altan [1 ]
Cakmak, Yusuf [1 ]
Sozmen, Fazli [2 ]
Ozdemir, Tugba [1 ]
Siemiarczuk, Aleksander [3 ]
Akkaya, Engin U. [1 ,4 ]
机构
[1] Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey
[2] Akdeniz Univ, Fac Arts & Sci, Dept Chem, TR-07058 Antalya, Turkey
[3] PTI Fast Kinet Lab, London, ON N6E 2S8, Canada
[4] Bilkent Univ, Dept Chem, TR-06800 Ankara, Turkey
关键词
dyes/pigments; energy transfer; fluorescence spectroscopy; fluorophores; Sonogashira coupling; HIGHLY EFFICIENT; DISTYRYL-BORADIAZAINDACENES; FLUORESCENT-PROBE; BORON; FUNCTIONALIZATION; CHEMOSENSOR; MODULATION; CHEMISTRY; EMISSION; LIBRARY;
D O I
10.1002/chem.200903449
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Multichromophoric boron-di-pyrromethene (Bodipy) dyes synthesized on phenylene-ethynylene platforms have been be converted to energy transfer cassettes in a one-step chemical transformation. Excitation energy transfer processes in these highly symmetrical derivatives were studied in detail, including time-resolved fluorescence spectroscopy techniques. Excitation spectra and the emission lifetimes suggest efficient energy transfer between the donor and acceptor chromophore. These novel energy transfer cassettes, while highlighting a short-cut approach to similar energy transfer systems, could be useful as large pseudo-Stokes shift multichromophoric dyes with potential applications in diverse applications.
引用
收藏
页码:6346 / 6351
页数:6
相关论文
共 57 条
[1]   A sensitive and selective ratiometric near IR fluorescent probe for zinc ions based on the distyryl-bodipy fluorophore [J].
Atilgan, Serdar ;
Ozdemir, Tugba ;
Akkaya, Engin U. .
ORGANIC LETTERS, 2008, 10 (18) :4065-4067
[2]   Water soluble distyryl-boradiazaindacenes as efficient photosensitizers for photodynamic therapy [J].
Atilgan, Serdar ;
Ekmekci, Zeynep ;
Dogan, A. Lale ;
Guc, Dicle ;
Akkaya, Engin U. .
CHEMICAL COMMUNICATIONS, 2006, (42) :4398-4400
[3]   Boradiazaindacene (Bodipy)-based building blocks for the construction of energy transfer cassettes [J].
Barin, Gokhan ;
Yilmaz, M. Deniz ;
Akkaya, Engin U. .
TETRAHEDRON LETTERS, 2009, 50 (15) :1738-1740
[4]   Novel Molecular Building Blocks Based on the Boradiazaindacene Chromophore: Applications in Fluorescent Metallosupramolecular Coordination Polymers [J].
Bozdemir, Oe. Altan ;
Buyukcakir, Onur ;
Akkaya, Engin U. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (15) :3830-3838
[5]   Tetrastyryl-Bodipy Dyes: Convenient Synthesis and Characterization of Elusive Near IR Fluorophores [J].
Buyukcakir, Onur ;
Bozdemir, O. Altan ;
Kolemen, Safacan ;
Erbas, Sundus ;
Akkaya, Engin U. .
ORGANIC LETTERS, 2009, 11 (20) :4644-4647
[6]   Phenylethynyl-BODIPY Oligomers: Bright Dyes and Fluorescent Building Blocks [J].
Cakmak, Yusuf ;
Akkaya, Engin U. .
ORGANIC LETTERS, 2009, 11 (01) :85-88
[7]   Functionalization of Boron Dipyrrin (BODIPY) Dyes through Iridium and Rhodium Catalysis: A Complementary Approach to α- and β-Substituted BODIPYs [J].
Chen, Jinping ;
Mizumura, Masatoshi ;
Shinokubo, Hiroshi ;
Osuka, Atsuhiro .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (24) :5942-5949
[8]   Effective PET and ICT switching of boradiazaindacene emission: A unimolecular, emission-mode, molecular half-subtractor with reconfigurable logic gates [J].
Coskun, A ;
Deniz, E ;
Akkaya, EU .
ORGANIC LETTERS, 2005, 7 (23) :5187-5189
[9]   Ion sensing coupled to resonance energy transfer: A highly selective and sensitive ratiometric fluorescent chemosensor for Ag(I) by a modular approach [J].
Coskun, A ;
Akkaya, EU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) :10464-10465
[10]   Bis(2-pyridyl)-substituted boratriazaindacene as an NIR-emitting chemosensor for Hg(II) [J].
Coskun, Ali ;
Yilmaz, M. Deniz ;
Akkaya, Engin U. .
ORGANIC LETTERS, 2007, 9 (04) :607-609