Disrupting aggregation of tethered rhodamine B dyads through inclusion in cucurbit[7]uril

被引:36
作者
Halterman, Ronald L. [1 ]
Moore, Jason L. [1 ]
Mannel, Lisa M. [1 ]
机构
[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA
关键词
D O I
10.1021/jo7026432
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hexano- and dodecano-tethered diesters of rhodamine B were prepared. The absorption and fluorescence spectra of these flexibly tethered dyads were compared with those of the rhodamine 3B ethyl ester. Increased J- and H-type dimer formation and decreased fluorescence emission were observed for the tethered dyads. Complexation of the cationic chromophoric units in cucurbit[7]uril (CB7) hosts decreased H-dimer aggregation, especially for the dodecano-tethered dyad. The monomeric dye and both dye dyads exhibited enhanced fluorescence upon addition of CB7.
引用
收藏
页码:3266 / 3269
页数:4
相关论文
共 41 条
[1]   Improving the properties of organic dyes by molecular encapsulation [J].
Arunkumar, E ;
Forbes, CC ;
Smith, BD .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (19) :4051-4059
[2]   Efficient fluorescence enhancement and cooperative binding of an organic dye in a supra-biomolecular host-protein assembly [J].
Bhasikuttan, Achikanath C. ;
Mohanty, Jyotirmayee ;
Nau, Werner M. ;
Pal, Haridas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (22) :4120-4122
[3]   A comparative analysis of photovoltaic principles governing dye-sensitized solar cells and p-n junctions [J].
Bisquert, J ;
García-Cañadas, J ;
Mora-Seró, I ;
Palomares, E .
ORGANIC PHOTOVOLTAICS IV, 2004, 5215 :49-59
[4]   Spectral properties of rhodamine 3B adsorbed on the surface of montmorillonites with variable layer charge [J].
Bujdak, Juraj ;
Martinez Martinez, Virginia ;
Lopez Arbeloa, Fernando ;
Iyi, Nobuo .
LANGMUIR, 2007, 23 (04) :1851-1859
[5]   Fluorescence emission and anisotropy from rhodamine dimers [J].
Burghardt, TP ;
Lyke, JE ;
Ajtai, K .
BIOPHYSICAL CHEMISTRY, 1996, 59 (1-2) :119-131
[6]   Molecular-dynamics simulations of pyronine 6G and rhodamine 6G dimers in aqueous solution [J].
Chuichay, Parawan ;
Vladimirov, Egor ;
Siriwong, Khatcharin ;
Hannongbua, Supot ;
Roesch, Notker .
JOURNAL OF MOLECULAR MODELING, 2006, 12 (06) :885-896
[7]   Dimerization of xanthene dyes in water:: Experimental studies and molecular dynamic simulations [J].
Daré-Doyen, S ;
Doizi, D ;
Guilbaud, P ;
Djedaïni-Pilard, F ;
Perly, B ;
Millié, P .
JOURNAL OF PHYSICAL CHEMISTRY B, 2003, 107 (50) :13803-13812
[8]   Energy dissipation in multichromophoric single dendrimers [J].
De Schryver, FC ;
Vosch, T ;
Cotlet, M ;
Van der Auweraer, M ;
Müllen, K ;
Hofkens, J .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (07) :514-522
[9]   Identification of oblique and coplanar inclined fluorescent J-dimers in rhodamine 110 doped sol-gel-glasses [J].
del Monte, F ;
Levy, D .
JOURNAL OF PHYSICAL CHEMISTRY B, 1999, 103 (38) :8080-8086
[10]   In vivo molecular and cellular imaging with quantum dots [J].
Gao, XH ;
Yang, LL ;
Petros, JA ;
Marshal, FF ;
Simons, JW ;
Nie, SM .
CURRENT OPINION IN BIOTECHNOLOGY, 2005, 16 (01) :63-72