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Molecules 2016, 21(11), 1541;

Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol)

Macromolecular Science Research Division, Institute for Catalysis and Graduate School of Chemical Sciences and Engineering, Hokkaido University, N21 W10, Kita-ku, Sapporo 001-0021, Japan
Integrated Research Consortium on Chemical Sciences (IRCCS), Institute for Catalysis, Hokkaido University, N21 W10, Kita-ku, Sapporo 001-0021, Japan
Author to whom correspondence should be addressed.
Academic Editor: Yoshio Okamoto
Received: 11 October 2016 / Revised: 7 November 2016 / Accepted: 11 November 2016 / Published: 16 November 2016
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(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. View Full-Text
Keywords: photo-polymerization; racemization; isomerization; excited states; reduction; 1,1′-bi(2-naphthol) photo-polymerization; racemization; isomerization; excited states; reduction; 1,1′-bi(2-naphthol)

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Zhang, Z.; Wang, Y.; Nakano, T. Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol). Molecules 2016, 21, 1541.

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