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Updated: Jun 15, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Synthesis and Photochemical Uncaging of Alkene-Protected, Polymer-Bound Vicinal Frustrated Lewis Pairs
Emily A Latif1, Jeremy D Hilgar1, Nathan A Romero1
1Department of Chemistry & Biochemistry, University of California San Diego, La Jolla, California 92093, United States.
Abstract:
Polymeric materials bearing Frustrated Lewis Pair (FLP) functionality are promising candidates for use as heterogeneous catalysts and adaptive materials, but synthetic access to FLP-functional polymers remains limited due to the incompatibility of FLPs with standard polymerization chemistries. Herein, we describe a synthetic approach that "cages" highly reactive vicinal phosphine-borane FLPs as covalent alkene adducts, which are stable to Ni-mediated vinyl addition polymerization. We discovered that the caged FLP adducts can be photochemically activated to liberate vicinal FLPs, enabling spatiotemporally controlled release of FLPs from polymeric precursors.
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