Direct synthesis of tetrazine functionalities on polymer backbones

Sinem Sipahioglu Kara, Mustafa Yasin Ateş, Gozde Deveci, Ahmet Cetinkaya, Muhammet U. Kahveci*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)673-680
Number of pages8
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume57
Issue number6
DOIs
Publication statusPublished - 15 Mar 2019

Bibliographical note

Publisher Copyright:
© 2018 Wiley Periodicals, Inc.

Funding

This work has been financially supported by Türkiye Bilimsel ve Teknolojik Aras¸tirma Kurumu and The Scientific and Technological Research Council of Turkey (TUBITAK, Project # 214M175). This work has been financially supported by T?rkiye Bilimsel ve Teknolojik Ara?tirma Kurumu and The Scientific and Technological Research Council of Turkey (TUBITAK, Project # 214M175).

FundersFunder number
TUBITAK
Türkiye Bilimsel ve Teknolojik Araştırma Kurumu214M175

    Keywords

    • ATRP
    • Diels–Alder click
    • functionalization of polymers
    • IEDDA
    • modification
    • post-polymerization
    • tetrazine

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