Excimer emission and energy transfer in cofacial boradiazaindacene (BODIPY) dimers built on a xanthene scaffold

被引:99
作者
Saki, N
Dinc, T
Akkaya, EU [1 ]
机构
[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
[2] Kocaeli Univ, Dept Chem, TR-41380 Izmir, Turkey
关键词
BODIPY dyes; energy transfer; multichromophoric systems; molecular switches;
D O I
10.1016/j.tet.2005.12.021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Using a rigid xanthene scaffold, a series of boradiazaindacene derivatives were synthesized. In some of these compounds, two boradiazaindacene derivatives were placed cofacially, resulting in significant inter-chromophoric interactions, including excimer emission. A simple modification of boradiazaindacene structure leads to formation of an ICT dye, which has distinct spectral properties. Energy transfer between two BODIPY dyes was demonstrated as well. In addition, the spectral properties of ICT dye can be modulated by the addition of the acid leading to an acid switchable, energy transfer cassette. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2721 / 2725
页数:5
相关论文
共 25 条
[1]   Dimers of dipyrrometheneboron difluoride (BODIPY) with light spectroscopic applications in chemistry and biology [J].
Bergström, F ;
Mikhalyov, I ;
Hägglöf, P ;
Wortmann, R ;
Ny, T ;
Johansson, LBÅ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (02) :196-204
[2]   Energy transfer cassettes based on BODIPY® dyes [J].
Burghart, A ;
Thoresen, LH ;
Chen, J ;
Burgess, K ;
Bergström, F ;
Johansson, LBÅ .
CHEMICAL COMMUNICATIONS, 2000, (22) :2203-2204
[3]   The Pacman effect: A supramolecular strategy for controlling the excited-state dynamics of pillared cofacial bisporphyrins [J].
Chang, CJ ;
Loh, ZH ;
Deng, YQ ;
Nocera, DG .
INORGANIC CHEMISTRY, 2003, 42 (25) :8262-8269
[4]   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
[5]   Difluorobora-s-diazaindacene dyes as highly selective dosimetric reagents for fluoride anions [J].
Coskun, A ;
Akkaya, EU .
TETRAHEDRON LETTERS, 2004, 45 (25) :4947-4949
[6]   Novel fluorescent chemosensor for anions via modulation of oxidative PET: a remarkable 25-fold enhancement of emission [J].
Coskun, A ;
Baytekin, BT ;
Akkaya, EU .
TETRAHEDRON LETTERS, 2003, 44 (30) :5649-5651
[7]   Physical and photophysical characterization of a BODIPY phosphatidylcholine as a membrane probe [J].
Dahim, M ;
Mizuno, NK ;
Li, XM ;
Momsen, WE ;
Momsen, MM ;
Brockman, HL .
BIOPHYSICAL JOURNAL, 2002, 83 (03) :1511-1524
[8]   Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe [J].
Gabe, Y ;
Urano, Y ;
Kikuchi, K ;
Kojima, H ;
Nagano, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3357-3367
[9]   Excited-state symmetry breaking in cofacial and linear dimers of a green perylenediimide chlorophyll analogue leading to ultrafast charge separation [J].
Giaimo, JM ;
Gusev, AV ;
Wasielewski, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (29) :8530-8531
[10]  
Haugland R.P., 1988, US pat, Patent No. [4,774,339, 4774339]