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

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Conjugated organic compounds with 3-phenyl-5-isoxazolone or N,N prime-diethylthiobarbituric acid acceptors have large first molecular hyperpolarizabilities (beta) in comparison with compounds with 4-nitrophenyl acceptors. For example, julolidinyl-(CH double bond CH)3-CH double bond N,N prime-diethylthiobarbituric acid, which has 12 atoms between the donor and acceptor, has a beta (0) of 911 times 10minus 30 electrostatic units, whereas (CH3)2 NC6 H4-(CH double bond CH)4-C6 H4 NO2, with 16 atoms between its donor and acceptor, has a beta (0) of 133 times 10minus 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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