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The synthesis and first full structural elucidation of a benzotriazole azo dye

Graham, D. and Kennedy, A.R. and Teat, S.J. (2000) The synthesis and first full structural elucidation of a benzotriazole azo dye. Journal of Heterocyclic Chemistry, 37 (6). pp. 1555-1558. ISSN 0022-152X

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Abstract

Although azo dyes containing benzotriazole are of interest as substrates for surface enhanced resonance Raman scattering, SERRS, little is known of their molecular structure due to their poor crystal growth properties. We recently synthesised a highly crystalline dihydroquinoline via an unusual condensation reaction and we report herein that the azo-benzotriazole dye subsequently formed was sufficiently crystalline to allow structural elucidation using synchroton radiation. It was found that this benzotriazole dye exists as the unexpected 6-isomer and the structure of the dihydroquinoline moiety changes markedly on coupling due to increased delocalisation.