Donor-Acceptor Interactions in Red-Emitting Thienylbenzene-Branched Dendrimers with Benzothiadiazole Core

被引:37
作者
Thomas, K. R. Justin [1 ]
Huang, Tai-Hsiang [1 ]
Lin, Jiann T. [1 ,2 ]
Pu, Shin-Chien [3 ]
Cheng, Yi-Ming [3 ]
Hsieh, Cheng-Chih [3 ]
Tai, Chou Pi [3 ]
机构
[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan
[2] Natl Cent Univ, Dept Chem, Chungli 320, Taiwan
[3] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
关键词
charge transfer; dendrimers; donor-acceptor systems; energy harvesting; luminescence;
D O I
10.1002/chem.200801694
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis and characterization of dendrimers containing thienylbenzene repeating units, red-emitting benzothiadiazole core, and triarylamine peripheries that bear naphthyl units are reported. The relevant dendrimers of different generations are classified as G(nb) (n = 1-3), while the tert-butyl dendrimers G(na) with the acceptor alone were also synthesized to serve as control chromophores that avoid donor-acceptor interactions. The resulting dendrimers are capable of harvesting photon energy through efficient energy transfer among donor-acceptor moieties, so that highly luminescent red fluorophores result. Transient fluorescence studies suggest that the energy transfer and its efficiency are approximately unity in all G(n) dendrimers, whereas the rate of energy transfer for the G(b) dendrimers is suppressed, that is, charge transfer from the core to the periphery is a significant quenching pathway. These dendrimers are amorphous in nature with high glass transition temperatures (176-201 degrees C). Electroluminescent devices were fabricated by using the dendrimers as hole-transporting emitters, and the devices exhibit promising red emission parameters.
引用
收藏
页码:11231 / 11241
页数:11
相关论文
共 50 条
[1]   Light-harvesting dendrimers [J].
Adronov, A ;
Fréchet, JMJ .
CHEMICAL COMMUNICATIONS, 2000, (18) :1701-1710
[2]   Energy and charge transfer dynamics in fully decorated benzyl ether dendrimers and their disubstituted analogues [J].
Ahn, Tai-Sang ;
Nantalaksakul, Arpornrat ;
Dasari, Raghunath R. ;
Al-Kaysi, Rabih O. ;
Muller, Astrid M. ;
Thayumanavan, S. ;
Bardeen, Christopher J. .
JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (48) :24331-24339
[3]  
[Anonymous], 1999, ANGEW CHEM, V111, P1519
[4]   Optical energy transport and interactions between the excitations in a coumarin-perylene bisimide dendrimer [J].
Augulis, Ramunas ;
Pugzlys, Audrius ;
Hurenkamp, Johannes H. ;
Feringa, Ben L. ;
van Esch, Jan H. ;
van Loosdrecht, Paul H. M. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2007, 111 (50) :12944-12953
[5]   Luminescent dendrimers. Recent advances [J].
Balzani, V ;
Ceroni, P ;
Maestri, M ;
Saudan, C ;
Vicinelli, V .
DENDRIMERS V: FUNCTIONAL AND HYPERBRANCHED BUILDING BLOCKS, PHOTOPHYSICAL PROPERTIES, APPLICATIONS IN MATERIALS AND LIFE SCIENCES, 2003, 228 :159-191
[6]   The development of light-emitting dendrimers for displays [J].
Burn, Paul L. ;
Lo, Shih-Chun ;
Samuel, Ifor D. W. .
ADVANCED MATERIALS, 2007, 19 (13) :1675-1688
[7]   Nonconjugated red-emitting dendrimers with p-type and/or n-type peripheries [J].
Chen, Chih-Hsin ;
Lin, Jiann T. ;
Yeh, Ming-Chang P. .
ORGANIC LETTERS, 2006, 8 (11) :2233-2236
[8]  
Choi M. S., 2004, ANGEW CHEM, V116, P152
[9]   Bioinspired molecular design of light-harvesting multiporphyrin arrays [J].
Choi, MS ;
Yamazaki, T ;
Yamazaki, I ;
Aida, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (02) :150-158
[10]   Energy transfer in dendritic macromolecules: Molecular size effects and the role of an energy gradient [J].
Devadoss, C ;
Bharathi, P ;
Moore, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (40) :9635-9644