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Updated: Mar 12, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Photo Racemization and Polymerization of (R)-1,1'-Bi(2-naphthol)
Zhaoming Zhang1, Yue Wang2, Tamaki Nakano3,4
1Macromolecular Science Research Division, Institute for Catalysis and Graduate School of Chemical Sciences and Engineering, Hokkaido University, N21 W10, Kita-ku, Sapporo 001-0021, Japan. zhang@polymer.cat.hokudai.ac.jp.
Abstract:
(R)-1,1'-Bi(2-naphthol) ((R)-BINOL) in an acetonitrile solution lost optical activity upon irradiation with an Hg-Xe lamp. HPLC resolution of the product indicated that (R)-BINOL was racemized upon irradiation, and SEC analysis suggested that a polymeric product was formed in the course of racemization. It is proposed that polymerization of BINOL can occur before it is racemized and that a unit in a polymer derived from BINOL may lose its optical activity afterwards due to in-chain racemization and/or reduction. The polymeric products seem to consist not only of BINOL residues but also of residues derived from acetonitrile as well as those derived through reduction of BINOL.
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