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Isomerizable N-alkylmerocyanine dyes as probes of micellar solubilization sites

The thermal cis to trans isomerization of N-alkylmerocyanine dyes is catalyzed by both cationic and anionic micelles. The catalysis by cationic micelles of hexadecyltrimethylammonium bromide (CTABr) increases markedly with substrate N-alkyl group length and is exceptionally pronounced for N-alkyl groups larger than pentyl. Rate data fit the pseudophase model of micellar catalysis for CTABr concentrations between 0.005 and 0.1 M and binding constants (K s ) and micellar rate constants (k m ) were evaluated. Both K s and k m increased dramatically as the N-alkyl group was varied from N-methyl to N-pentyl so that the increase in catalysis with substrate hydrophobicity is due not only to increased substrate binding to the micelle but also to enhanced reactivity within the micelle