Direct synthesis of tetrazine functionalities on polymer backbones

Kara S., Ateş M. Y., Deveci G., Cetinkaya A., Kahveci M. Ü.

Journal of Polymer Science, Part A: Polymer Chemistry, vol.57, no.6, pp.673-680, 2019 (SCI-Expanded, Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 57 Issue: 6
  • Publication Date: 2019
  • Doi Number: 10.1002/pola.29308
  • Journal Name: Journal of Polymer Science, Part A: Polymer Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.673-680
  • Keywords: ATRP, Diels–Alder click, functionalization of polymers, IEDDA, modification, post-polymerization, tetrazine
  • Bilecik Şeyh Edebali University Affiliated: No

Abstract

Tetrazine mediated inverse Electron Demand Diels–Alder Reaction (IEDDA) is an important modification technique due to its high selectivity and super-fast kinetics. Incorporation of tetrazine moieties on polymer chains requires multistep synthetic pathways and a post-polymerization step leading to functional polymeric materials. Such approaches involve separate syntheses of polymer and the molecule which will be employed in modification. Herein, we introduce a straightforward synthetic approach for direct synthesis of tetrazine groups on polymers as side chains. As model systems, tetrazine functional poly(N-isopropylacrylamide)-and poly(ethylene glycol)-based polymers from corresponding precursor polymers with nitrile moieties as pendant groups are prepared and IEDDA Click Reaction is achieved with trans-cyclooctene derivatives. The click reaction is monitored by both NMR and UV–vis spectroscopies. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 673–680.