Expanding the alternating propagation-chain transfer-based polymerization toolkit: the iodo-ene reaction

Timothy F. Scott, Joseph C. Furgal, Christopher J. Kloxin

Research output: Contribution to journalArticleResearchpeer-review

9 Citations (Scopus)

Abstract

Analogous to the thiol-ene and phosphane-ene polymerizations, radical-mediated iodo-ene reactions are described here that proceed via alternating propagation and chain transfer (i.e., APT) reactions between perfluoroiodide- and vinyl-bearing monomers. The thermal polymerization of a diiodo/tetraene formulation yielded a cross-linked, homogeneous polymer that was approximately seven times as radiopaque as aluminum owing to its high iodine content. Visible-light photopolymerizations of model iodo-ene monomers were monitored using mid-IR spectroscopy, revealing that the perfluoroiodide functional group consumption exceeded that of the vinyl, a discrepancy that decreased with increasing irradiation intensities and hence polymerization rates. The functional group conversions in resin formulations with a large initial perfluoroiodide excess exacerbated secondary side reactions that led to off-stoichiometric functional group consumption; nevertheless, photopolymerization of resin formulations with excess vinyl stoichiometry proceeded according to the ideal APT mechanism.

Original languageEnglish
Pages (from-to)1404-1409
Number of pages6
JournalACS Macro Letters
Volume4
Issue number12
DOIs
Publication statusPublished - 15 Dec 2015
Externally publishedYes

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