Synthesis of Poly(crown ether)s via Cyclopolymerization and Their Host Property

Abstract

Cyclopolymerization, which does not need a cyclic derivative as monomer, is a direct method for producing rings and polymer chain at the same time.Monomers forming 5–7 membered-rings have been generally studied.We established the synthesis of polymers with macrocyclic units via cyclopolymerization of bifunctional monomers containing oxyethylene units.Poly (crown ether) s and poly (cryptande)s are synthesized through the polymerizations of divinyl ethers and diepoxides, poly (thia-crown ether) s through diepisulfides, and poly (crown lactone)s through the monomers having acrylic and allylic groups.These polymers except for poly (crown lactone)s consist essentially of cyclic constitutional repeating units, and have the cation-binding properties.Cyclopolymerization of divinyl ethers is a facile method for producing optically active poly (crown ether)s which exhibit chiral recognition towards α-amino acids.For the cyclopolymerization of divinyl ether derived from chiral 3,3ʹ-disubstituted-1, 1ʹ-bi-2-naphthol, the asymmetric induction in the polymer main chain was concluded by the analysis of 1H NMR spectra of polymers. © 1990, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.