Guidelines To Select the N-Heterocyclic Carbene for the Organopolymerization of Monomers with a Polar Group

Laura Falivene, Luigi Cavallo

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

We report on the DFT stability of zwitterion and spirocycle adducts of five polar monomers with nine N-heterocyclic carbenes (NHC), covering the most typical classes of monomers and NHCs used in organopolymerization. Results indicate that the relative stability of the two adducts is dominated by the singlet-triplet energy gap of the free NHC, with low energy gaps favoring the spirocycle adduct, while high energy gaps favor the zwitterionic adduct. This basic structure/property relationship can be tuned by the hindrance of the NHC and the nature of the monomer. In addition to rationalize existing systems, the 45 NHC/monomer combinations we examined can be used as a guideline to predict the behavior of a new NHC/monomer combination.
Original languageEnglish (US)
Pages (from-to)1394-1401
Number of pages8
JournalMacromolecules
Volume50
Issue number4
DOIs
StatePublished - Feb 13 2017

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