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Issue 6, 2001
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Cationic π-electron systems with high quadratic hyperpolarisability

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Abstract

Cationic NLO-chromophores based on tolane π-systems in which conventional electron donors are combined with ionic pyridinio or triorganoammonio and -phosphonio substituents, respectively, perform much better than conventional donor/acceptor-substituted (D/A-substituted) tolanes concerning their hyperpolarisability–transparency trade-off. This effect occurs because ionic acceptors do not enlarge the π-system in contrast to conventional acceptors. The same holds true for benzene-type chromophores. Despite their different electronic nature, the extrapolated maximal high-energy absorption of the ionic chromophore series as well as of the conventional donor/acceptor-tolanes coincide at the absorption energy of unsubstituted tolane. This proves that the maximal blue transparency of a given series of substituted chromophores is governed by the absorption maximum of the unsubstituted parent chromophore. In this way chromophores have been designed with much higher quadratic hyperpolarisability than e.g.p-nitroaniline at about the same absorption wavelength. By applying the same concept, a two- and a three-dimensional highly efficient octupolar NLO-chromophore assembly has also been synthesised.

Graphical abstract: Cationic π-electron systems with high quadratic hyperpolarisability

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Publication details

The article was received on 01 Dec 2000, accepted on 03 Apr 2001 and first published on 10 May 2001


Article type: Paper
DOI: 10.1039/B009664B
J. Chem. Soc., Perkin Trans. 2, 2001, 964-974

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    Cationic π-electron systems with high quadratic hyperpolarisability

    C. Lambert, W. Gaschler, G. Nöll, M. Weber, E. Schmälzlin, C. Bräuchle and K. Meerholz, J. Chem. Soc., Perkin Trans. 2, 2001, 964
    DOI: 10.1039/B009664B

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