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Published January 28, 1994 | metadata_only
Journal Article

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


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 x 10^(-30) electrostatic units, whereas (CH_3)_2NC_6H_4,–(CH=CH)_4–C_6H_4NO_2, with 16 atoms between its donor and acceptor, has a β(0) of 133 x 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.

Additional Information

© 1994 American Association for the Advancement of Science. 16 August 1993; Accepted 1 December 1993. The work in this paper was performed in part at the Center for Space Microelectronics Technology, Jet Propulsion Laboratory, California Institute of Technology, under contract with the National Aeronautics and Space Administration. The work was sponsored by the Advanced Research Projects Agency through a contract administered by the Air Force Office of Scientific Research and by the Ballistic Missiles Defense Organization, Innovative Science and Technology Office. Support from the National Science Foundation is also gratefully acknowledged. We thank W. P. Schaefer for performing the crystallographic determinations, J. Murdoch for assistance in synthesizing some of the compounds, and J.-M. Lehn for helpful discussions. The characterizing data for the compounds in Table 1 are available from the authors upon request.

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August 20, 2023
August 20, 2023