title: A novel chiral mesoporous binaphthyl-silicas: preparation, characterization, and application in HPLC.
abstract: Mesoporous organosilicas with both R-(+)-1,1'-binaphthyl-2,2'-diamine and ethane moieties bridging in the framework were synthesized. This mesoporous material was prepared via the one-step co-condensation of N,N'-bis-[(triethoxysilyl)propyl]-(R)-bis-(ureido)-binaphthyl (Si-DABN) with 1,2-bis(triethoxysilyl)ethane (BTSE) using octadecyltrimethylammonium chloride (C(18) TMACl) as a structural directing agent with the aid of a co-solvent (ethanol) in basic medium. The morphology of these bifunctionalized mesoporous organosilicas is sensitive to the Si-DABN mole fraction and the base concentration. And the mesostructure becomes less ordered as the mole fraction of Si-DABN in the initial mixture increases from 10 to 40%. Elemental analysis and Fourier transform infrared (FT-IR) spectrometer indicate that the binaphthyl diamine was successfully introduced to the mesoporous organosilicas. Acidic conditions are more suitable than basic ones for the hydrolysis and condensation of (R)-2,2'-dicyanomethoxy-6,6'-di[(2-triethoxysilyl)ethenyl]-1,1'-binaphthyl, a chiral silane precursors with a short silane side chain on the binaphthyl group. A column packed with these bifunctionalized mesoporous organosilica spheres exhibits greater selectivity for R/S-1,1'-bi-2,2'-naphthol than one packed with commercial SiO(2)  grafted with N,N'-bis-[(triethoxysilyl)propyl]-(R)-bis-(ureido)-binaphthyl. Binaphthol and bromosubstituted binaphthol were fully resolved, but two ether derivatives were only partially enantioseparated and the other three ester derivatives were no fully resolved on the column via co-condensation method.
authors.affiliation: Department of Pharmaceutical Analysis, China Pharmaceutical University, Nanjing, China.
authors.forename: Ruixue
authors.initials: R
authors.lastname: Ran
authors.forename: Linjun
authors.initials: L
authors.lastname: You
authors.forename: Bin
authors.initials: B
authors.lastname: Di
authors.forename: Weiqiang
authors.initials: W
authors.lastname: Hao
authors.forename: Mengxiang
authors.initials: M
authors.lastname: Su
authors.forename: Fang
authors.initials: F
authors.lastname: Yan
authors.forename: Lili
authors.initials: L
authors.lastname: Huang
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation* / Q000379:methods; D009281:Naphthalenes / Q000737:chemistry; D010316:Particle Size; D004364:Pharmaceutical Preparations / Q000032:analysis*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry; D016062:Porosity; D058428:Silica Gel / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D009281:Naphthalenes; D004364:Pharmaceutical Preparations; D011108:Polymers; D058428:Silica Gel; C412330:1,1'-binaphthyl