A hydrogen-bonded polymer constructed from mechanically interlocked, suit[1]ane monomers

Abstract

A T-shaped 2,4,7-substituted benzimidazolium “axle” with two ester functionalities and a 24-membered crown ether “wheel” with appendages containing terminal olefin groups were threaded — axle through wheel — to form a [2]pseudorotaxane. Grubbs’ ring-closing metathesis (RCM) was then used to form a third loop and create a bicyclic cage that fully encapsulates the axle and permanently interlocks the two molecular components creating a suit[1]ane. There are no bulky groups on the axle to prevent unthreading, but the axle is trapped due to the cage-like nature of the newly created polyether host. After hydrolysis of the esters groups to carboxylic acids, this novel mechanically interlocked molecule (MIM) polymerizes in the solid state. The structure of the resulting supramolecular polymer was determined by single-crystal X-ray diffraction and contains linear one-dimensional tapes of suit[1]ane monomers linked by intermolecular hydrogen bonding between the carboxylic acid groups.