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Synthesis and Anion Binding Properties of 2,5-Diamidothiophene Polypyrrole Schiff Base Macrocycles

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posted on 10.11.2005, 00:00 authored by Jonathan L. Sessler, Vladimir Roznyatovskiy, G. Dan Pantos, Natalya E. Borisova, Marina D. Reshetova, Vincent M. Lynch, Victor N. Khrustalev, Yuri A. Ustynyuk
Two easy-to-synthesize polypyrrolic 2,5-diamidothiophene Schiff base macrocycles are reported, along with their anion binding properties as determined via UV−vis spectroscopic titrations carried out in dichloroethane. There is a striking difference between the interactions with anions of the two macrocycles, a finding ascribed to differences in their rigidity. For example, the more flexible dipyrromethane-derived macrocycle displays a 1.2:1 hydrogen sulfate versus nitrate selectivity, while its more rigid bipyrrole-derived congener shows a 7.4:1 selectivity in favor to hydrogen sulfate.