Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles |
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| Authors: | Sessler Jonathan L Roznyatovskiy Vladimir Pantos G Dan Borisova Natalya E Reshetova Marina D Lynch Vincent M Khrustalev Victor N Ustynyuk Yuri A |
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| Institution: | Department of Chemistry and Biochemistry and Institute for Cellular and Molecular Biology, University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-0165, USA. sessler@mail.utexas.edu |
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| Abstract: | reaction: see text] 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. |
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