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

作者：Xiao, Duoduo; Zhang, Dengqing; Chen, Beihua; Xie, Dahai; Xiang, Yunjie; Li, Xianying^*; Jin, Wusong

来源：Langmuir, 2015, 31(39): 10649-10655.

DOI：10.1021/acs.langmuir.5b02273

• LIGHT-EMITTING CHARACTERISTICS
• SHAPE-PERSISTENT MACROCYCLES
• CONJUGATED MACROCYCLES
• ASSOCIATION BEHAVIOR
• NANOTUBE
• NANOSTRUCTURES
• ARCHITECTURES
• MOLECULES
• ACETYLENE
• CHEMISTRY

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 pi-conjugated m-phenylene pyrimidinylene alternated macrocyde 1(6mer) 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 superset of G3) in dichloromethane resulting in an enhanced and red-shifted fluorescence. H-1 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 x 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, 1(6mer) could not form self-assembled nanotubes in CHCl3 or tetrahydrofuran (THF) solution, leading to weak or no size-selective recognizability, respectively.

• 出版日期2015-10-6
• 单位东华大学