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Synfacts 2006(4): 0334-0334  
DOI: 10.1055/s-2006-932059
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Derivatives of Octaethynylphenazine and Hexaethynylquinoxaline

Contributor(s): Timothy M. Swager, Mark S. Taylor
S. Miao, C. G. Bangcuyo, M. D. Smith, U. H. F. Bunz*
Georgia Institute of Technology, Atlanta and University of South Carolina, Columbia, USA
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

The preparation of alkynylated heterocycles 2 and 3, by condensation reactions of tetraalkynylphenylenediamine 1 with diketones, is reported. The introduction of alkynyl groups effects a decrease of the band gap of the quinoxaline and phenazine chromophores, and alters their metal-binding properties. Silver(I) cations bind tightly to 3, due to the proximity of the electron-rich alkynes to the Lewis basic nitrogen atom.