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 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 182
  • Publication Date: 2019
  • Doi Number: 10.1016/j.polymer.2019.121844
  • Journal Name: POLYMER
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Keywords: Unsaturated polyester, Organocatalyst, Thiol-Michael, Aza-Michael, Postfunctionalization, POST-POLYMERIZATION MODIFICATION, SEQUENTIAL MICHAEL ADDITION, MACROMOLECULAR DESIGN, THIOL, FUNCTIONALIZATION, POLYMERS, POLY(BETA-THIOESTER)S
  • Istanbul Technical University Affiliated: Yes

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.