Efficient Post-Polymerization modification of pendant aldehyde functional polymer via reductive etherification reaction

Emre Akar, Dilhan Kandemir, Serter Luleburgaz, Volkan Kumbaraci*, Hakan Durmaz

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The aldehydes have always been a privilege in polymer science since the aldehyde carbonyl readily undergoes several reactions efficiently under mild conditions, ranging from non-aldol reactions to multicomponent reactions, mostly without any additive. In the current study, the versatility of the aldehyde group has been further exploited using the reductive etherification reaction (RER), which has proven to be a useful synthetic strategy to convert aldehyde or ketone carbonyls to ethers in the presence of organosilane compounds. For this purpose, a polymer platform containing pendant aldehyde units was synthesized via free radical polymerization (FRP) and modified with a variety of alcohols using chlorodimethylsilane (CDMS) as the reducing agent. The spectroscopic analyses indicated that pendant aldehydes successfully turned to corresponding ethers with quantitative or near quantitative RER efficiencies. The proposed strategy was also extended to thiols and the resultant polymers were found to be in thioacetal and/or thioether pendant forms. Given the growing demand for the development of new synthetic methodologies that can be adapted to the macromolecular level, a new insight into the modification of aldehyde-functionalized polymers has been introduced in this study.

Original languageEnglish
Article number111440
JournalEuropean Polymer Journal
Volume177
DOIs
Publication statusPublished - 15 Aug 2022

Bibliographical note

Publisher Copyright:
© 2022 Elsevier Ltd

Funding

This work was supported by the Scientific Research Projects Department of Istanbul Technical University (ITU BAP Project Number: TYL-2021-43461) and The Scientific and Technological Research Council of Turkey (TUBITAK, Project Number: 119Z516).

FundersFunder number
Türkiye Bilimsel ve Teknolojik Araştırma Kurumu119Z516
Istanbul Teknik Üniversitesi
Bilimsel Araştırma Projeleri Birimi, İstanbul Teknik ÜniversitesiTYL-2021-43461

    Keywords

    • Aldehyde
    • Chlorodimethylsilane
    • Post-polymerization modification
    • Reductive etherification reaction

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