The chiral recognition of optically active poly(triphenylmethyl methacrylate) derivatives as stationary phases for HPLC.

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概要

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• Four <I>meta</I>-halogen- or <I>meta</I>-methyl-substituted optically active poly(triphenylmethyl methacrylate) [poly(TrMA)] derivatives with a one-handed helical structure were coated on macroporous silica gel and their chiral-recognition abilities as stationary phases for high-pherformance liquid chromatography were investigated with methanol or hexane–2-propanol (95:5(v/v)) as the eluent. The chiral-recognition abilities of poly(<I>m</I>-fluorophenyldiphenylmethyl methacrylate) and poly(<I>m</I>-chlorophenyldiphenylmethyl methacrylate) were slightly low compared with that of poly(TrMA) when methanol was used as the eluent. Poly[tris(<I>m</I>-chlorophenyl)methyl methacrylate] [poly(<I>m</I>-Cl<SUB>3</SUB>TrMA)] showed no resolving ability, although poly[tris(<I>m</I>-tolyl)methyl methacrylate] [poly(<I>m</I>-Me<SUB>3</SUB>TrMA)] had an effective chiral recognition ability and resolved some racemates more efficiently than poly(TrMA). When hexane–2-propanol (95/5) was used as the eluent, the optical-resolution abilities of all these chiral polymers except for poly(<I>m</I>-Cl<SUB>3</SUB>TrMA) were rather similar to that of poly(TrMA) under the same eluent system. The chiral-adsorbing sites are considered to be the chiral triarylmethyl propellers in the methanol system; carbonyl groups may also be involved in the hexane–2-propanol system. The difference in the chiral-recognition abilities of the two tri-substituted chiral polymers were ascribed to their different propeller structures and/or the different conformations of their carbonyl groups. The optical-resolution abilities of poly[TrMA-<I>co</I>-(<I>m</I>-Cl<SUB>3</SUB>TrMA)] and poly[TrMA-<I>co</I>-(<I>m</I>-Me<SUB>3</SUB>TrMA)] were also investigated. From the results, the mechanism of the separation of enantiomers on poly(TrMA) was discussed.

• 公益社団法人 日本化学会の論文

著者

• Yashima Eiji

  Department Of Applied Chemistry Faculty Of Engineering Nagoya University

• Hatada Koichi

  Department Of Chemistry Faculty Of Engineering Science Osaka University

• Okamoto Yoshio

  Department Of Applied Chemistry Faculty Of Engineering Nagoya University

• Ishikura Motoshi

  Department of Chemistry, Faculty of Engineering Science, Osaka University

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