Synthesis and study of a calixpyrrole-texaphyrin chimera: A new oligopyrrolic chloride anion receptor

Reported here is the synthesis and characterization of a new class of macrocycle that represents a hybrid between texaphyrin and calixpyrrole. These polypyrrolic macrocycles were prepared in one step by the acid-catalyzed condensation between diformyl dipyrromethanes and o-phenylenediamines in high yields. The X-ray crystal structure of one of these new “chimeras” was solved. It reveals that the diprotonated Schiff-base macrocycle has a V-shape in which one chloride anion is bound. Isothermal titration calorimetry (ITC) studies served to confirm the ability of the hybrid macrocycles to bind chloride anion in acetonitrile solution. These compounds may be useful as easy-to-make anion receptors.