Add time:07/14/2019         Source:sciencedirect.com

A series of N2,N6-bis(3-methoxypropyl)pyridine-2,6-diamine azo dyes, prepared by coupling 2,6-bis((3-methoxypropyl)amino)-4-methylnicotinonitrile and diazotized substituted anilines with distinguishable electron push-pull abilities, have been described in this paper. The new dyes undergoing double functional group transformation (FGT) show extremely high pH stability compared to corresponding mono FGT dyes, which could be ascribed to the introduction of the second 3-methoxypropylamino group forming the new pyridine-2,6-diamine backbone. It is noted that the unusual transformation from D−π−A to A−π−D system has been verified for our multi-substituted phenyl-azo-pyridine FGT products. The adjustment of electron-donating and electron-withdrawing phenyl and pyridine substituted groups narrows the discrepancy of electron push-pull capabilities for dizao and coupling components, which makes possible the transformation for roles of donor and acceptor. It is believed that the achievement of extremely high pH stability for pyridine-2,6-diamine based heterocyclic azo dyes is regarded as a useful exploration for designing new FGT modified pyridone dyes.

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