Functionalized axles derived from 1,2-bis(benzimidazolium)ethane for the self assembly of [2]pseudorotaxanes with 24-crown-8 wheels

ORGN 192

Jorge Tiburcio, jtiburcio@cinvestav.mx and Surisadai I. Moreno. Departamento de Quimica, Centro de Investigacion y de Estudios Avanzados, Avenida IPN 2508, Zacatenco, Mexico, D.F, 07360, Mexico
The successful development of machines at molecular scale, based on the bottom-up approach, relies on the precise design and preparation of functional components that can be organized into more sophisticated systems. Some of the most promising systems are based on interlocked molecules, which can be obtained by the penetration of a linear molecule –axle- through the cavity of a cyclic molecule -wheel- to generate an interpenetrated complex or [2]pseudorotaxane. We have previously proved that 1,2-bis(benzimidazolium)ethane cations can penetrate the cavity of dibenzo-24-crown-8 macrocycles to produce a new family of pH-controlled [2]pseudorotaxanes. In this contribution we will present the design, synthesis, solution NMR and X- ray crystallographic studies of new N-functionalized axles derived from 1,2-bis(benzimidazolium)ethane cations and their ability to generate [2]pseudorotaxanes with 24-crown-8 ether wheels.