title: Size-selective recognition by a tubular assembly of phenylene-pyrimidinylene alternated macrocycle through hydrogen-bonding interactions.
abstract: Study of artificial tubular assemblies as a useful host scaffold for size-selective recognition and release of guest molecules is an important subject in host-guest chemistry. We describe well-defined self-assembled nanotubes (NT6mer) formed from π-conjugated m-phenylene-pyrimidinylene alternated macrocycle 16mer that exhibit size-selective recognition toward a specific aromatic acid. In a series of guest molecules, a size-matched trimesic acid (G3) gives inclusion complexes (NT6mer⊃G3) in dichloromethane resulting in an enhanced and red-shifted fluorescence. (1)H nuclear magnetic resonance (NMR) titration experiments indicated that the complex was formed in a 1:1 molar ratio. Density functional theory (DFT) calculations and the binding constant value (K = 1.499 × 10(5) M(-1)) of NT6mer with G3 suggested that the complex involved triple hydrogen-bonding interactions. The encapsulated guest G3 molecules can be readily released from the tubular channel through the dissociation of hydrogen bonding by the addition of a polar solvent such as dimethylsulfoxide (DMSO). In contrast, 16mer could not form self-assembled nanotubes in CHCl3 or tetrahydrofuran (THF) solution, leading to weak or no size-selective recognizability, respectively.
authors.affiliation: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University , 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China.
authors.forename: Duoduo
authors.initials: D
authors.lastname: Xiao
authors.affiliation: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University , 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China.
authors.forename: Dengqing
authors.initials: D
authors.lastname: Zhang
authors.affiliation: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University , 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China.
authors.forename: Beihua
authors.initials: B
authors.lastname: Chen
authors.affiliation: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University , 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China.
authors.forename: Dahai
authors.initials: D
authors.lastname: Xie
authors.affiliation: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University , 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China.
authors.forename: Yunjie
authors.initials: Y
authors.lastname: Xiang
authors.affiliation: School of Environmental Science and Engineering, Donghua University , 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China.
authors.forename: Xianying
authors.initials: X
authors.lastname: Li
authors.affiliation: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University , 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China.
authors.forename: Wusong
authors.initials: W
authors.lastname: Jin
mesh_terms: D006860:Hydrogen Bonding; D047028:Macrocyclic Compounds / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy
chemical_list: D047028:Macrocyclic Compounds