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Size-Selective Recognition by a Tubular Assembly of Phenylene–Pyrimidinylene Alternated Macrocycle through Hydrogen-Bonding Interactions

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journal contribution
posted on 06.10.2015 by Duoduo Xiao, Dengqing Zhang, Beihua Chen, Dahai Xie, Yunjie Xiang, Xianying Li, Wusong Jin
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 (NT6merG3) in dichloromethane resulting in an enhanced and red-shifted fluorescence. 1H 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 × 105 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.