A bicyclic host molecule 1  consisting of a pillar[5]arene and a 1,5-dioxynaphthalene-based crown ether has been synthesized and structurally characterized. The pillar[5]arene and the 1,5-dioxynaphthalene-based crown ether components in 1  were found to selectively recognize two guest molecules, namely 1,4-dicyanobutane G1  and paraquat G2 , respectively, of different shapes, sizes and electronic constitutions. The discriminative molecular recognition behavior possessed by the two macrocyclic receptor units in 1  toward G1  and G2  is determined by their different noncovalent modes of binding toward substrates. The binding affinity of the pillar[5]arene unit in 1  toward G1 , as well as that of the 1,5-dioxynaphthalene-based crown ether unit in 1  toward and G2 , was investigated in solution by using 1D and 2D 1H NMR spectroscopies. Additionally, the simultaneous taking up of G1  and G2  by 1  was demonstrated both in solution and in the solid state.

Pilllar[5]arene and crown ether fused bicyclic host, guest discrimination, and simultaneous binding of two different guests

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.