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Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical P.pdf

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Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical P

Molecules 2002, 7, 320-330 molecules ISSN 1420-3049 Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines A. C. Pardal1, S. S. Ramos2, P. F. Santos1, L. V. Reis1 and P. Almeida2,* 1 Departamento de Química, Universidade de Trás-os-Montes e Alto Douro, Apartado 202, 5001-911 Vila Real Codex, Portugal. Tel. 351(259)350273, Fax 351(259)350480 2 Departamento de Química e Unidade de Materiais Têxteis e Papeleiros, Universidade da Beira Interior, Rua Marquês dávila e Bolama, 6200-001 Covilh?, Portugal. Tel. 351(275)319761, Fax 351(275)319730 * Author to whom correspondence should be addressed; e-mail: pjsa@alpha2.ubi.pt Received: 23 October 2001; in revised form 18February 2002 / Accepted: 26 February 2002 / Published: 31 March 2002 Abstract: The synthesis and spectroscopic characterisation of some representative N-alkyl- substituted quaternary ammonium salts derived from benzothiazole, benzoxazole, benzo- selenazole, indole and quinoline are described. These heterocyclic salts, bearing an activated methyl group in the 2-position in relation to the nitrogen atom and N-methyl, -pentyl, -hexyl and -decyl chains, are typical precursors of cyanine dyes. Keywords: Heterocyclic quaternary ammonium salts, cyanines precursors, spectroscopic characterisation. Introduction Despite the fact that several N-alkyl quaternary ammonium salts bearing a 2-methylbenzothiazole, -benzoselenazole, -benzoxazole, -indole and -quinoline nuclei are easily found in the literature, mainly as unisolated precursors of cyanine dyes [1-3], their full physical and spectroscopic characterisation is Molecules 2002, 7 321 not usually described. To the best of our knowledge, for some of those most commonly used for the synthesis of cyanines, namely the N-ethyl, -pentyl, -hexyl and -decyl substituted ones, only the 1H-NMR spectral data for the N-ethyl quaternary salts [4,5] and the 13C-NMR spectral data for