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Molecules 2016, 21(11), 1541; doi:10.3390/molecules21111541

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

1
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
2
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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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. 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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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