Helix-sense-selective radical polymerization of N- (Triphenylmethyl) methacrylamides and properties of the polymers

Abstract

N-(Triphenylmethyl)methacrylamide (TrMAM) and N(4-butylphenyl)- phenylmethyl]methacrylamide (DBuTrMAM) were polymerized using a radical initiator. The obtained poly(TrMAM) was insoluble in common organic solvents, but poly(DBuTrMAM) was soluble in chloroform and THF. Both polymers were dissolved in cone. H2SO4 accompanied by cleavage of the side groups to give poly(methacrylamide) (poly(MAM)). The 1H NMR of the polymers in D2SO4 indicated that the polymers obtained at low temperature were nearly 100% isotactic. The poly(MAM) with almost 100% isotacticity showed a crystallinity. The poly(DBuTrMAM) formed a lyotropic crystalline phase in chloroform. The radical polymerization of the monomers in the presence of various chiral additives produced optically active polymers having a prevailing helicity. The optically active poly(TrMAM) exhibited a low chiral recognition. © 2006 The Society of Polymer Science, Japan.