Phase transfer catalysis for tandem alkylation of azo dyes for the synthesis of novel multifunctional molecules

Potentially photorefractive molecules, which possess both a charge transfer component and a nonlinear optical chromophore, were prepared by the direct N-monoalkylation of Disperse Orange 3 (1) with a carbazole alkyl bromide ( 2) utilizing phase transfer catalysis. Further N-alkylation of the remainin g active N-H with alkyl halides with various chain lengths allowed the ther mal properties of the Disperse Orange 3 derivatives to be fine-tuned. (C) 2 000 Elsevier Science Ltd. All rights reserved.