title: Evaluation of "click" binaphthyl chiral stationary phases by liquid chromatography.
abstract: Two "click" binaphthyl chiral stationary phases were synthesized and evaluated by liquid chromatography. Their structures incorporate S-(-)-1,1'-binaphthyl moiety as the chiral selector and 1,2,3-triazole ring as the spacer. These chiral stationary phases (CSPs) allowed the efficient resolution for a wide range of racemic BINOL derivatives, particularly for nonpolar diether derivatives and 3-phenyl indolin-2-one analogs. The chromatographic data showed that the π-π interaction was crucial for enantiorecognition of these CSPs. Loss of enantioselectivity observed on CSP3, which are lacking the triazole ring linkage, indicated that the triazole ring linkage took part in the enantioseparation process, although it was remote from the chiral selector of the CSP. The substitution of the phenyl group at 6 and 6' positions can significantly improve the separation ability of the CSP. The chiral recognition mechanism was also investigated by tracking the elution orders and studying the thermodynamic parameters.
authors.affiliation: Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
authors.forename: Hui
authors.initials: H
authors.lastname: Yu
authors.forename: Chenghua
authors.initials: C
authors.lastname: Yin
authors.forename: Cunyu
authors.initials: C
authors.lastname: Jia
authors.forename: Yu
authors.initials: Y
authors.lastname: Jin
authors.forename: Yanxiong
authors.initials: Y
authors.lastname: Ke
authors.forename: Xinmiao
authors.initials: X
authors.lastname: Liang
mesh_terms: D002853:Chromatography, Liquid / Q000379:methods*; D057930:Click Chemistry / Q000379:methods*; D007211:Indoles / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013696:Temperature; D013816:Thermodynamics; D014230:Triazoles / Q000737:chemistry
chemical_list: D007211:Indoles; D009281:Naphthalenes; C475744:S(-)2,2'-dihydroxy-1,1'-binaphthyl; D014230:Triazoles; C456900:indolin-2-one; C412330:1,1'-binaphthyl