Acetylene Dicarboxylic Acid Diallyl Ester: A Versatile Monomer for Thiol–Ene Photocured Networks

Ozgun Daglar, Emrah Çakmakçi (Corresponding author), Ufuk Saim Gunay, Gurkan Hizal, Umit Tunca, Hakan Durmaz

Research output: Contribution to journalArticleAcademicpeer-review

15 Citations (Scopus)

Abstract

Thiol–ene photopolymerization (TEP) is a highly advantageous method for the curing of unsaturated monomers, and the design of novel monomers to be used in TEP is an active area of research. The feasibility and the versatility of novel acetylene dicarboxylic acid diallyl ester (ACDAE)-based monomers are synthesized and demonstrated. The electron deficient acetylenic core in ACDAE allows to apply three different click reactions, aza-Michael, thio-Michael, and metal-free azide–alkyne cycloaddition reactions, efficiently on it. Thus, three novel allylic monomers are synthesized and are used to prepare thiol–ene photopolymerized networks. All monomers are synthesized in good yields and structurally characterized by 1H NMR and Fourier-transform infrared spectroscopy (FTIR) measurements. Thermal, thermomechanical, and mechanical properties, flame retardancy, transmittance, and the wettability of the networks are determined.

Original languageEnglish
Article number2100427
Number of pages12
JournalMacromolecular Materials and Engineering
Volume306
Issue number11
DOIs
Publication statusPublished - Nov 2021
Externally publishedYes

Keywords

  • acetylene dicarboxylic acid diallyl ester
  • aza-Michael
  • metal-free azide–alkyne cycloaddition reaction
  • thio-Michael
  • thiol–ene photopolymerization

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