Post-synthetic modification of a macrocyclic receptor via regioselective imidazolium ring-opening.

ABSTRACT: A facile post-synthetic modification of a tetracationic tetraimidazolium macrocycle, 1⁴⁺ (i.e., the "Texas-sized" molecular box (cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,4-dimethylenebenzene)), is described. Under mild basic conditions, ring-opening of the imidazolium moieties occurs. This results in two new isomeric dicationic macrocycles. This simple yet efficient modification serves to alter the size of the molecular cavity, the charge of the macromolecular receptor, and the manner whereby it interacts with dianionic guest molecules. The isomeric mixture of imidazolium ring opened macrocycles can be synthesized in relatively high overall yield (86-93%). The reaction shows regioselectivity and the ratio of major to minor (i.e., trans :

SUBMITTER: Shang J 

PROVIDER: S-EPMC6014093 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature