Extremely rapid postfunctionalization of maleate and fumarate main chain polyesters in the presence of TBD


Daglar O., Tunca Ü. , Tunca Ü. , Hızal G. , Tunca Ü. , Durmaz H.

POLYMER, vol.182, 2019 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 182
  • Publication Date: 2019
  • Doi Number: 10.1016/j.polymer.2019.121844
  • Title of Journal : POLYMER
  • Keywords: Unsaturated polyester, Organocatalyst, Thiol-Michael, Aza-Michael, Postfunctionalization, POST-POLYMERIZATION MODIFICATION, SEQUENTIAL MICHAEL ADDITION, MACROMOLECULAR DESIGN, THIOL, FUNCTIONALIZATION, POLYMERS, POLY(BETA-THIOESTER)S

Abstract

Unsaturated polyester (UP) scaffold, poly (butylene maleate) (P1), possessing an electron-deficient double bond in the main chain was prepared and utilized as a precursor for thiol- and aza-Michael addition reactions. From a detailed catalyst search (amidine and guanidine bases), 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) proved to be the most efficient catalyst for thiol-Michael addition reactions since pendant thioether functional polyesters were achieved quantitatively within 1 min. Furthermore, P1 was allowed to react with primary and secondary amines through aza-Michael addition reactions, followed by thiol-Michael addition reaction thus affording the synthesis of pendant amine and thioether functional polyesters.