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PHENYLENE HOMOLOGS OF BENZIDINE: MUTAGENICITY AND USE IN DYE/PIGMENT SYNTHESIS
Citation:
Freeman, H. S., J. Wang, AND L D. Claxton. PHENYLENE HOMOLOGS OF BENZIDINE: MUTAGENICITY AND USE IN DYE/PIGMENT SYNTHESIS. Presented at Colorchem '04, 10th Inter'l Conference on Pigments, Dyes & Functional Dyes, Spindleruv Mlyn, Czech Republic, May 23-27-04.
Description:
In a previous paper in this area, we reported results from studies pertaining to the use of molecular modeling methods in predicting the properties of some Congo Red analogs containing 4,4'-diaminoterphenyl (DATP) and 4,4'-diaminoquarterphenyl (DAQP) in lieu of the benzidine moiety [1]. Based on those results, we expected a progressively hypsochromic shift in ?max as the number of phenylene groups increased. With this in mind, we conducted studies aimed at providing experimental data to help validate the modeling results and to assess the chemical and biological properties of these interesting conjugated systems.
The present paper pertains to the synthesis of DATP and DAQP as homologs of 4,4'diaminobiphenyl (benzidine, DABP) and a determination of 1) the utility of these diamines as intermediates for dye and pigment synthesis and 2) their mutagenic properties. Following their synthesis, the diamine structures were confirmed using 1H NMR and EI-MS, and the standard Ames test [2] and Prival modification [3] were used to assess mutagenicity. Of special interest to us was the determination of a possible correlation between the number of phenylene groups in type 1 compounds and the mutagenicity of the diamines and colorants they afford.