Anion Binding by Electron-Deficient Arenes Based on Complementary Geometry and Charge Distribution

Abstract

Extended electron-deficient arenes are investigated as potential neutral receptors for polyanions. Anion binds via sigma interaction with extended arenes, which are composed solely of C and N ring atoms and CN substituents. As a result, the positive charge on the aromatic C is enhanced, consequently maximizing binding strength. Selectivity is achieved because different charge distributions can be obtained for target anions of a particular geometry. The halides F- and Cl- form the most stable complex with 6, while the linear N-3(-) interacts most favorably with 7. The trigonal NO3- and tetrahedral ClO4- fit the 3-fold rotational axis of 6 but do not form stable complexes with 5 and 7. The Y-shaped HCOO- forms complexes with 4, 5, and 7, with the latter being the most stable. Thus, the anion complexes exhibit strong binding and the best geometrical fit between guest and host, reminiscent of Lego blocks.