Aromatic plane effect study in pseudorotaxane construction between 'Texas-sized' molecular box and carboxylate anions

作者：Tang, Feng; Cao, Rui^*; Gong, Han-Yuan

来源：Tetrahedron Letters, 2015, 56(6): 820-823.

DOI：10.1016/j.tetlet.2014.12.111

• Supramolecular chemistry
• Self assembly
• Pseudorotaxane
• Aromatic plane
• Carboxylate anion binding

This study focused on the aromatic plane effect of the binding modes between 'Texas-sized' molecular box and carboxylate anion species. The molecular box, namely cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)-[2](1,4-dimethylenebenzene) (1(4+); studied as the PF6- salt), easily constructs interpenetrated structures (i.e., pseudorotaxanes) with carboxylate anions via the introduction of aromatic rings. As revealed by H-1 NMR titration, two-dimensional nuclear Overhauser effect spectroscopy (NOESY), UV-Vis spectroscopic study, and electrospray ionization mass spectrometry (ESI-MS), the determination effect of aromatic plane in the binding modes between 1(4+) and carboxylate anions was studied in detail. This research reveals the important role of aromatic plane substitute groups on anions for building anion-induced interpenetrated self-assembly structures.

• 出版日期2015-2-4
• 单位北京师范大学; 中国人民大学