title: Influence of Helical Structure on Chiral Recognition of Poly(phenylacetylene)s Bearing Phenylcarbamate Residues of L-Phenylglycinol and Amide Linage as Pendants.
abstract: Four poly(phenylacetylene)s (PPA-1~4) bearing phenylcarbamate residues of L-phenylglycinol and amide linkage as pendants were prepared to be used as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC), and the influences of coating solvents, dimethylformamide (DMF) and tetrahydrofuran (THF), which were used for coating the polymers on silica gel, on the helical structure of the polymers and their chiral recognition abilities were investigated. The structure analysis of PPA-1~4 by (1) H nuclear magnetic resonance (NMR), size exclusion chromatography (SEC), optical rotation, and circular dichroism (CD) spectra indicated that the polymers possess the cis-transoidal structure with dynamic helical conformation. The polymers in THF seem to have shorter conjugated helical main chains along with a tighter twist conformation than those in DMF. The chiral recognition abilities of PPA-1~4 with the different helical structures induced by the coating solvents were evaluated as the CSPs in HPLC. The helical structures of PPA-1~4 induced with THF are preferable for chiral recognition for some racemates compared to those induced with DMF, and higher chiral recognition abilities of PPA-1~ were achieved using THF.
authors.affiliation: Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China.
authors.forename: Chunhong
authors.initials: C
authors.lastname: Zhang
authors.affiliation: Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China.
authors.forename: Rui
authors.initials: R
authors.lastname: Ma
authors.affiliation: Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China.
authors.forename: Hailun
authors.initials: H
authors.lastname: Wang
authors.affiliation: Department of Materials Chemistry, Asahikawa National College of Technology, Asahikawa, Japan.
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Sakai
authors.affiliation: Division of Biotechnology and Macromolecular Chemistry, Graduate School of Chemical Sciences and Engineering, Faculty of Engineering, Hokkaido University, Sapporo, Japan.
authors.forename: Toshifumi
authors.initials: T
authors.lastname: Satoh
authors.affiliation: Division of Biotechnology and Macromolecular Chemistry, Graduate School of Chemical Sciences and Engineering, Faculty of Engineering, Hokkaido University, Sapporo, Japan.
authors.forename: Toyoji
authors.initials: T
authors.lastname: Kakuchi
authors.affiliation: Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China.
authors.forename: Lijia
authors.initials: L
authors.lastname: Liu
authors.affiliation: Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China.|Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Japan.
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Okamoto
mesh_terms: D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D004983:Ethanolamines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000577:Amides; D002254:Carbonates; D004983:Ethanolamines; C519145:poly(phenylacetylene); C005332:N-phenylethanolamine; D000114:Acetylene
keywords: CSP; HPLC; chiral recognition; helical structure; poly(phenylacetylene)