Synthesis and characterisation of monomethine cyanine dyes based on N-bridgehead heterocycles

Authors: El-Aal, R M Abd; Koraiem, A I M; El-Deen, N M Salah

Source: Coloration Technology, Volume 121, Number 4, 2005 , pp. 228-236(9)

Publisher: Society of Dyers and Colourists

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Abstract:

In this paper, the synthesis and spectral properties of novel asymmetrical and symmetrical monomethine cyanine dyes are described. Reaction of phenylpyrazolones and oxazolones with acetyl thiourea and/or thiosemicarbazide afforded acetyl intermediate compounds which were then reacted with metal divalent chlorides, followed by reaction with N-methyl hetetrocyclic quaternary salts, to give asymmetrical monomethine cyanine dyes. Reaction of the 5-amino derivative of the intermediate compounds with acetaldehyde followed by reaction with N-methyl hetetrocyclic quaternary salts produced the symmetrical monomethine cyanine dyes. These new compounds were characterised with elemental analyses, visible absorption and infrared spectrometry, and ¹H/¹³C NMR and mass spectroscopy. The correlation between the colour and structure of these dyes was also investigated. Received: 8 March 2005; Accepted&colon: 31 May 2005.

Document Type: Regular paper

Affiliations: 1: Chemistry Department, Aswan Faculty of Science, South Valley University, Aswan, Egypt. : abdelal2001@yahoo.com

Publication date: 2005-01-01

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