Abstract: A triple hydrogen bonding interaction effectively controlled the stereochemistry during radical polymerization of acylamide derivatives. An acrylamide monomer, in which amide (proton donor site, D) and pyridine (proton acceptor site, A) moieties were arrayed in the DAD sequence, was polymerized in the presence of a cyclic imide as the ADA-type receptor in CHCl3 to give syndiotactic polymers (r = 72%) even at 60 C while atactic polymers (r = 43%) were obtained without the mediator. Furthermore, the simultaneous control of the tacticity and the molecular weights of the polymers were attained by RAFT polymerization in the presence of the mediator.

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