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

Marder, Seth R. and Cheng, Lap-Tak and Tiemann, Bruce G. and Friedli, Andrienne C. and Blanchard-Desce, Mireille and Perry, Joseph W. and Skindhøj, Jørgen (1994) Large First Hyperpolarizabilities in Push-Pull Polyenes by Tuning of the Bond Length Alternation and Aromaticity. Science, 263 (5146). pp. 511-514. ISSN 0036-8075. https://resolver.caltech.edu/CaltechAUTHORS:20150122-112800747

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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 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1126/science.263.5146.511DOIArticle
http://www.sciencemag.org/content/263/5146/511PublisherArticle
http://www.jstor.org/stable/2883030JSTORArticle
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.
Funders:
Funding AgencyGrant Number
NASAUNSPECIFIED
Advanced Research Projects Agency (ARPA)UNSPECIFIED
Air Force Office of Scientific Research (AFOSR)UNSPECIFIED
Ballistic Missile Defense OrganizationUNSPECIFIED
NSFUNSPECIFIED
Issue or Number:5146
Record Number:CaltechAUTHORS:20150122-112800747
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150122-112800747
Official Citation:Marder, S. R., Cheng, L.-T., Tiemann, B. G., Friedli, A. C., Blanchard-Desce, M., Perry, J. W., & Skindhøj, J. (1994). Large First Hyperpolarizabilities in Push-Pull Polyenes by Tuning of the Bond Length Alternation and Aromaticity. Science, 263(5146), 511-514. doi: 10.1126/science.263.5146.511
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:53993
Collection:CaltechAUTHORS
Deposited By: Joanne McCole
Deposited On:22 Jan 2015 20:28
Last Modified:03 Oct 2019 07:54

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