High hyperpolarizabilities of donor-p-acceptor-functionalized calix[4]arene derivatives by pre-organization of chromophores

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Kenis, Paul J.A. and Kerver, Esther G. and Snellink-Ruel, Bianca H.M. and Hummel van, Gerrit J. and Harkema, Sybolt and Flipse, Marinus C. and Woudenberg, Richard H. and Engbersen, Johan F.J. and Reinhoudt, David N. (1998) High hyperpolarizabilities of donor-p-acceptor-functionalized calix[4]arene derivatives by pre-organization of chromophores. European Journal of Organic Chemistry, 1998 (6). pp. 1089-1098. ISSN 1434-193X

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Abstract:A systematic investigation of the conceptofpre-organization of nonlinear optical (NLO) active chromophoric groups in calix[4]arene derivatives and the influence on the absolute second-order nonlinear optical coefficients is reported. Several calix[4]arenes were synthesized by modification of the electron-withdrawing groups at the upper rim of the aromatic and extension of the conjugated system of the pre-organized chromophoric groups. Electrical field induced second harmonic generation (EFISH) experiments showed high (0) values up to 1165·10-48 esu. Compared with the corresponding reference compounds, enhancements of the (0) values varying up to 2.5 times per chromophore were observed which proves the benefit of pre-organization of NLO-active units in a multi-chromophoric system. Another important advantage is that the increase in NLO activity observed for these systems is not accompanied with a shift of the absorption band to longer wavelengths exceeding 20 nm. This makes these calix[4]arene derivatives promising building blocks for the development of stable, NLO-active materials that are suitable for frequency doubling.
Item Type:Article
Copyright:© 1998 WILEY-VCH Verlag
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/10980
Official URL:http://dx.doi.org/10.1002/(SICI)1099-0690(199806)1998:6<1089::AID-EJOC1089>3.0.CO;2-T
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Metis ID: 105934