Site-isolated electro-optic chromophores based on substituted 2,2′-bis(3,4-propylenedioxythiophene) π-conjugated bridges

被引:96
作者
Hammond, Scott R. [1 ]
Clot, Olivier [1 ]
Firestone, Kimberly A. [1 ]
Bale, Denise H. [1 ]
Lao, David [1 ]
Haller, Marnie [2 ]
Phelan, Gregory D. [1 ]
Carlson, Brenden [1 ]
Jen, Alex K. -Y. [2 ]
Reid, Philip J. [1 ]
Dalton, Larry R. [1 ]
机构
[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA
[2] Univ Washington, Dept Mat Sci & Engn, Seattle, WA 98195 USA
关键词
D O I
10.1021/cm800054y
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Application of bis(propylenedioxythiophene) (bis(ProDOT)) pi-conjugated bridges bearing alkyl or aryl substituents in electro-optic (EO) chromophores is presented. A series of three bis (ProDOT)-based chromophores and a bithiophene-based control chromophore were prepared and fully characterized with regard to EO applications. The highly planar bis(ProDOT) bridge results in slightly larger (similar to 10%) molecular hyperpolarizability (beta) values as compared to the bithiophene bridge, as measured by hyper-Rayleigh scattering at a variety of wavelengths. In amorphous polycarbonate guest-host films, however, the bulky substituents on the bis(ProDOT) bridge result in significantly larger (similar to 70%) poling-induced EO coefficient (r(33)) values, as measured by simple reflection ellipsometry at 1310nm. This can be attributed to a roughly 2-fold enhancement in poling efficiency due to reduced intermolecular dipole-dipole interactions. This chromophore architecture also exhibits excellent temporal alignment stability and photochemical stability as compared to benchmark AJL8, FTC, and CLD chromophore systems. Incorporation of the strong CF3-phenyl-substituted tricyano-furan (TCF) acceptor into a bis(ProDOT)based chromophore resulted in a beta(zzz)( - 2 omega;omega,omega) value at 1907 nm of 5700 +/- 400 x 10(-30) esu and an r(33) value of 69 +/- 14 pm/V at 32.8 total chromophore weight %.
引用
收藏
页码:3425 / 3434
页数:10
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