Phenylethynyl-BODIPY Oligomers: Bright Dyes and Fluorescent Building Blocks

被引:123
作者
Cakmak, Yusuf [3 ]
Akkaya, Engin U. [1 ,2 ]
机构
[1] Bilkent Univ, Dept Chem, TR-06800 Ankara, Turkey
[2] Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey
[3] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
关键词
RESONANCE ENERGY-TRANSFER; DISTYRYL-BORADIAZAINDACENES; QUANTUM YIELDS; CHEMOSENSOR; EMISSION; COMPLEXES; CHEMISTRY; EFFICIENT; RECEPTOR; DIMERS;
D O I
10.1021/ol802446e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Boradiazaindacene dyes were converted Into phenylethynyl-BODIPY oligomers via a cycle of reactions, notably including Sonogashira couplings. As expected, as the number, n, of repeating units Increases, peak absorption and emission wavelengths are shifted to the red end of the visible spectrum, albeit with smaller increments as n Increases, Decyl groups help to keep the solubility remarkably high, and in addition to being very bright red-emitting fluorophores, their rigid rod-like structures could allow their use as functional building blocks.
引用
收藏
页码:85 / 88
页数:4
相关论文
共 34 条
[1]   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
[2]   A highly potassium-selective ratiometric fluorescent indicator based on BODIPY azacrown ether excitable with visible light [J].
Baruah, M ;
Qin, WW ;
Vallée, RAL ;
Beljonne, D ;
Rohand, T ;
Dehaen, W ;
Boens, N .
ORGANIC LETTERS, 2005, 7 (20) :4377-4380
[3]  
Birge R., 1987, Kodak Laser Dyes
[4]   3,5-diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes:: Synthesis, spectroscopic, electrochemical, and structural properties [J].
Burghart, A ;
Kim, HJ ;
Welch, MB ;
Thoresen, LH ;
Reibenspies, J ;
Burgess, K ;
Bergstrom, F ;
Johansson, LBÅ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7813-7819
[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]   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
[7]   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
[8]   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
[9]   Distyryl-boradiazaindacenes: facile synthesis of novel near IR emitting fluorophores [J].
Dost, Zeynep ;
Atilgan, Serdar ;
Akkaya, Engin U. .
TETRAHEDRON, 2006, 62 (36) :8484-8488
[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