Synthesis and Anion Binding Properties of 2,5-Diamidothiophene Polypyrrole Schiff Base Macrocycles
datasetposted on 10.11.2005 by Jonathan L. Sessler, Vladimir Roznyatovskiy, G. Dan Pantos, Natalya E. Borisova, Marina D. Reshetova, Vincent M. Lynch, Victor N. Khrustalev, Yuri A. Ustynyuk
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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.