Expanding sapphyrin: towards selective phosphate binding |
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Authors: | Katayev Evgeny A Boev Nikolay V Myshkovskaya Ekaterina Khrustalev Victor N Ustynyuk Yu A |
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Institution: | Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St., 28, Moscow, 119991, Russia. katayev@ineos.ac.ru |
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Abstract: | The anion-templated syntheses and binding properties of novel macrocyclic oligopyrrole receptors in which pyrrole rings are linked through amide or imine bonds are described. The efficient synthesis was accomplished by anion-templated 1+1] Schiff-base condensation and acylation macrocyclization reactions. Free receptors and their host-guest complexes with hydrochloric acid, acetic acid, tetrabutylammonium chloride, and hydrogen sulfate were analyzed by single-crystal X-ray diffraction analysis. Stability constants with different tetrabutylammonium salts of inorganic acids were determined by standard 1H NMR and UV/Vis titration techniques in D6]DMSO/0.5% water solution. According to the titration data, receptors containing three pyrrole rings (10 and 12) exhibit high affinity (log Ka=5-7) for bifluoride, acetate, and dihydrogen phosphate, and interact weakly with chloride and hydrogen sulfate. The amido-bipyrrole receptors 11 and 13 with four pyrrole rings exhibit 10(4)- and 10(2)-fold selectivity for dihydrogen phosphate, respectively, as inferred from competitive titrations in the presence of tetrabutylammonium acetate. |
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Keywords: | host–guest systems phosphates receptor pyrroles receptors template synthesis |
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