title: Self-assembly behavior of tail-to-tail superstructure formed by mono-6-O-(4-carbamoylmethoxy-benzoyl)-β-cyclodextrin in solution and the solid state.
abstract: A novel mono-modified β-cyclodextrin (β-CD) consisting of 4-carbamoylmethoxy-benzoyl unit at the primary side was synthesized and its self-assembly behavior was determined by X-ray crystallography and NMR spectroscopy. The crystal structure shows a 'Yin-Yang'-like packing mode, in which the modified β-CD exhibits a channel superstructure formed by a tail-to-tail dimer as the repeating motif with the substituted group embedded within the hydrophobic cavity of the facing β-CD. The geometry of the substituted group is determined by the inclusion of the cavity and is further stabilized by two intermolecular hydrogen bonds between the carbonyl O atom and phenyl group. Furthermore, NMR ROESY investigation indicates that the self-assembly behavior of the substituted group within the β-CD cavity is retained in aqueous solution, and the effective binding constant Ka was calculated to be 1330 M(-1) by means of (1)H NMR titration according to iterative determination.
authors.affiliation: College of Sciences, Tianjin University of Science and Technology, Tianjin 300222, PR China.
authors.forename: Zhe
authors.initials: Z
authors.lastname: Xu
authors.affiliation: College of Sciences, Tianjin University of Science and Technology, Tianjin 300222, PR China.
authors.forename: Xin
authors.initials: X
authors.lastname: Chen
authors.affiliation: College of Sciences, Tianjin University of Science and Technology, Tianjin 300222, PR China.
authors.forename: Jing
authors.initials: J
authors.lastname: Liu
authors.affiliation: College of Sciences, Tianjin University of Science and Technology, Tianjin 300222, PR China.
authors.forename: Dong-Qing
authors.initials: DQ
authors.lastname: Yan
authors.affiliation: College of Sciences, Tianjin University of Science and Technology, Tianjin 300222, PR China.
authors.forename: Chun-Hua
authors.initials: CH
authors.lastname: Diao
authors.affiliation: College of Sciences, Tianjin University of Science and Technology, Tianjin 300222, PR China. Electronic address: guomj@tust.edu.cn.
authors.forename: Min-Jie
authors.initials: MJ
authors.lastname: Guo
authors.affiliation: College of Sciences, Tianjin University of Science and Technology, Tianjin 300222, PR China. Electronic address: zhifan@tust.edu.cn.
authors.forename: Zhi
authors.initials: Z
authors.lastname: Fan
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008969:Molecular Sequence Data; D012996:Solutions; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000081:Acetamides; D012996:Solutions; D047392:beta-Cyclodextrins; C031215:betadex
keywords: Crystal structure; Self-assembly behavior; Supramolecular chemistry; β-Cyclodextrin