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Issue 41, 2013
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Synthesis of charged bis-heteroaryl donor–acceptor (D–A+) NLO-phores coupling (π-deficient–π-excessive) heteroaromatic rings

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Abstract

Charged chromophores based on heteroaromatic cations were prepared by reaction of alkylazinium salts with N-heteroarylstannanes under Stille conditions. This approach provides easy access to potential single donor D–A+ chromophores in which the acceptor moiety A+ is the pyridinium cation and the donors are different π-excessive N-heterocycles. The β hyperpolarizabilities were measured in hyper-Rayleigh scattering experiments and the experimental data are supported by a theoretical analysis that combines a variety of computational procedures, including density functional theory and correlated Hartree–Fock-based methods. In some chromophores, the absence of a bridge between donor and acceptor fragments increases the NLO properties.

Graphical abstract: Synthesis of charged bis-heteroaryl donor–acceptor (D–A+) NLO-phores coupling (π-deficient–π-excessive) heteroaromatic rings

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Publication details

The article was received on 06 Jun 2013, accepted on 22 Aug 2013 and first published on 22 Aug 2013


Article type: Paper
DOI: 10.1039/C3OB41159A
Org. Biomol. Chem., 2013,11, 7145-7154

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    Synthesis of charged bis-heteroaryl donor–acceptor (D–A+) NLO-phores coupling (π-deficient–π-excessive) heteroaromatic rings

    M. A. Ramirez, R. Custodio, A. M. Cuadro, J. Alvarez-Builla, K. Clays, I. Asselberghs, F. Mendicuti, O. Castaño, J. L. Andrés and J. J. Vaquero, Org. Biomol. Chem., 2013, 11, 7145
    DOI: 10.1039/C3OB41159A

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