Tuning octopolar NLO chromophores: Synthesis and spectroscopic characterization of persubstituted 1,3,5-tris(ethynylphenyl)benzenes

被引:51
作者
Hennrich, G [1 ]
Asselberghs, I
Clays, K
Persoons, A
机构
[1] Autonomous Univ Madrid, Dept Quim Organ, Madrid 28049, Spain
[2] Univ Leuven, Dept Chem, B-3001 Heverlee, Belgium
关键词
D O I
10.1021/jo049279i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a series of octopolar 1,3,5-tris(ethynylphenyl)benzenes via Sonogashira coupling is described, varying the substituents on both the central benzene core as well as the acetylenic periphery. In particular, systems bearing an electron-rich core and an electron-poor periphery are obtained that display advanced optical properties. The linear (by UV-vis and fluorescence spectroscopy) and second-order nonlinear optical properties are studied, the latter by hyper-Rayleigh scattering (HRS) (Hendrickx, E.; Clays, K.; Persoons, A. Acc. Chem. Res. 1998, 31, 675-683). The influence of different core and periphery substitution is revealed by the optical properties and confirms the possibility of fine-tuning those. Because of the presence of (one-photon) fluorescence for all compounds, femtosecond hyper-Rayleigh scattering has been applied (Olbrechts, G.; Strobbe, R.; Clays, K.; Persoons, A. Rev. Sci. Instrum. 1998, 69, 2233-2241). The implementation of the deconvolution in the frequency domain allows for a demodulation and a phase shift between immediate (nonlinear) scattering and time-delayed (multiphoton) fluorescence for high modulation frequencies (Wostyn, K.; Binnemans, K.; Clays, K.; Persoons, A. Rev. Sci. Instrum. 2001, 72, 32153220). In accordance with the linear optical properties, the second-order NLO properties can also be tuned by varying the core and peripheric substitutents.
引用
收藏
页码:5077 / 5081
页数:5
相关论文
共 43 条
[1]   Light-harvesting dendrimers [J].
Adronov, A ;
Fréchet, JMJ .
CHEMICAL COMMUNICATIONS, 2000, (18) :1701-1710
[2]  
Beljonne D, 2002, ADV FUNCT MATER, V12, P631, DOI 10.1002/1616-3028(20020916)12:9<631::AID-ADFM631>3.0.CO
[3]  
2-W
[4]   OPTICAL NONLINEARITIES IN CHEMISTRY - INTRODUCTION [J].
BURLAND, DM .
CHEMICAL REVIEWS, 1994, 94 (01) :1-2
[5]   Synthesis, self-assembly, and switching of one-dimensional nanostructures from new crowded aromatics [J].
Bushey, ML ;
Nguyen, TQ ;
Nuckolls, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) :8264-8269
[6]   Octupolar crystals for nonlinear optics: 1,3,5-trinitro-2,4,6-tris(styryl)benzene derivatives [J].
Cho, BR ;
Lee, SJ ;
Lee, SH ;
Son, KH ;
Kim, YH ;
Doo, JY ;
Lee, GJ ;
Kang, TI ;
Lee, YK ;
Cho, MH ;
Jeon, SJ .
CHEMISTRY OF MATERIALS, 2001, 13 (05) :1438-+
[7]   1,3,5-tricyano-2,4,6-tris(vinyl)benzene derivatives with large second-order nonlinear optical properties [J].
Cho, BR ;
Park, SB ;
Lee, SJ ;
Son, KH ;
Lee, SH ;
Lee, MJ ;
Yoo, J ;
Lee, YK ;
Lee, GJ ;
Kang, TI ;
Cho, MH ;
Jeon, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (26) :6421-6422
[8]   ORGANOTHALLIUM COMPOUNDS .18. THE EFFECT OF ANTIMONY PENTAFLUORIDE AND FLUOROSULFURIC ACID ON THE THALLATION OF POLYFLUOROARENES [J].
DEACON, GB ;
SMITH, RNM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (08) :1587-1597
[9]   Synthesis and nonlinear optical, photophysical, and electrochemical properties of subphthalocyanines [J].
del Rey, B ;
Keller, U ;
Torres, T ;
Rojo, G ;
Agulló-López, F ;
Nonell, S ;
Martí, C ;
Brasselet, S ;
Ledoux, I ;
Zyss, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :12808-12817
[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