Controlled synthesis of anthracene-labeled omega-amine polystyrene to be used as a probe for interfacial reaction with mutually reactive PMMA

Anthracene-labeled polystyrene (PS) end-capped by a primary amine has been synthesized by atom transfer radical copolymerization of styrene with 3-isopropenyl-alpha,alpha-dimethylbenzyl isocyanate (m-TMI). The m-TMI co-monomer (5.7 mol-%) does not perturb the control of the radical polymerization of styrene. The pendant isocyanate groups of the copolymer chains of low polydispersity (M-w/M-n = 1.25) and controlled molecular weight (up to 35 000) have been derivatized into anthracene by a reaction with 9-methyl(aminomethyl)anthracene. The anthracene-labeled PS (ca. 2 mol-% label) has been conveniently analyzed by size-exclusion chromatography with a UV detector (SEC-UV). Moreover, the omega-bromide end-group of the copolymer chains has been derivatized into a primary amine, making the labeled PS chains reactive towards non-miscible poly(methyl methacrylate) (PMMA) chains end-capped by an anhydride. The interfacial coupling of the mutually reactive PS and PMMA chains has been studied under static conditions (i.e., at the interface between thin PS and PMMA films) and successfully analyzed by SEC-UV.