Modification of electron deficient polyester via Huisgen/Passerini sequence


Lüleburgaz S., Hızal G., Durmaz H., Tunca Ü.

POLYMER, vol.127, pp.45-51, 2017 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 127
  • Publication Date: 2017
  • Doi Number: 10.1016/j.polymer.2017.08.055
  • Journal Name: POLYMER
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.45-51
  • Keywords: Electron deficient polyester, Huisgen 1,3-dipolar cycloaddition reaction, Passerini reaction, Post-functionalization, Atom economic, Ambient temperature, PASSERINI 3-COMPONENT REACTION, MULTICOMPONENT REACTIONS, FUNCTIONALIZED POLYMERS, BLOCK-COPOLYMERS, CLICK REACTIONS, CHEMISTRY, POLYMERIZATION, TERPOLYMERS, DENDRIMERS, DIVERSITY

Abstract

In this work, we functionalized a polyester backbone via sequential Huisgen 1,3-dipolar cycloaddition and 3-component Passerini reactions. First, we directly introduced the carboxyl acid functionality onto the electron deficient polyester using Huisgen 1,3-dipolar cycloaddition protocol in N,N-dimethyl formamide at 40 degrees C for 16 h. This acid functional polyester was further modified by Passerini reaction using two types of isocyanides and a variety of aldehydes in CH2Cl2 at room temperature for 24 h. Both protocols are atom economic, highly efficient, need no additional catalyst and proceed at ambient temperature. The products were characterized using spectroscopic and chromatographic techniques such as NMR, IR and GPC, respectively. (C) 2017 Elsevier Ltd. All rights reserved.