title: Photo Racemization and Polymerization of (R)-1,1'-Bi(2-naphthol).
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.
authors.affiliation: 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. zhang@polymer.cat.hokudai.ac.jp.
authors.forename: Zhaoming
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: 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. yue.wang@cat.hokudai.ac.jp.
authors.forename: Yue
authors.initials: Y
authors.lastname: Wang
authors.affiliation: 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. tamaki.nakano@cat.hokudai.ac.jp.|Integrated Research Consortium on Chemical Sciences (IRCCS), Institute for Catalysis, Hokkaido University, N21 W10, Kita-ku, Sapporo 001-0021, Japan. tamaki.nakano@cat.hokudai.ac.jp.
authors.forename: Tamaki
authors.initials: T
authors.lastname: Nakano
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D008027:Light; D009284:Naphthols / Q000737:chemistry*; D055668:Photochemical Processes; D058105:Polymerization; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D009284:Naphthols; C028405:2-naphthol
keywords: 1,1′-bi(2-naphthol); excited states; isomerization; photo-polymerization; racemization; reduction