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Large First Hyperpolarizabilities in Push-Pull Polyenes by Tuning of the Bond Length Alternation and Aromaticity

Seth R. Marder, Lap-Tak Cheng, Bruce G. Tiemann, Andrienne C. Friedli, Mireille Blanchard-Desce, Joseph W. Perry and Jørgen Skindhøj
Science
New Series, Vol. 263, No. 5146 (Jan. 28, 1994), pp. 511-514
Stable URL: http://www.jstor.org/stable/2883030
Page Count: 4
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Large First Hyperpolarizabilities in Push-Pull Polyenes by Tuning of the Bond Length Alternation and Aromaticity
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Abstract

Conjugated organic compounds with 3-phenyl-5-isoxazolone or N,N′-diethylthiobarbituric acid acceptors have large first molecular hyperpolarizabilities (β) in comparison with compounds with 4-nitrophenyl acceptors. For example, julolidinyl-(CH=CH)$_3$-CH=N,N′-diethylthiobarbituric acid, which has 12 atoms between the donor and acceptor, has a β(0) of 911 × 10$^{-30}$ electrostatic units, whereas (CH$_3$)$_2$NC$_6$H$_4$-(CH=CH)$_4$-C$_6$H$_4$NO$_2$, with 16 atoms between its donor and acceptor, has a β(0) of 133 × 10$^{-30}$ electrostatic units. The design strategies demonstrated here have resulted in chromophores that when incorporated into poled-polymer electrooptic modulators exhibited significant enhancements in electrooptic coefficients relative to polymers containing the commonly used dye Disperse Red-1. Poled polymer devices based on these or related chromophores may ultimately lead to high-speed electrooptic switching elements with low drive-power requirements, suitable for telecommunications applications.

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