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Phenanthroline Complexes Bearing Fused Dipyrrolylquinoxaline Anion Recognition Sites: Efficient Fluoride Anion Receptors.
journal contribution
posted on 2002-01-25, 00:00 authored by Toshihisa Mizuno, Wen-Hao Wei, Leah Renee Eller, Jonathan L. SesslerNovel anion recognition host molecules, tris-1,10-phenanthroline cobalt(III) and bis-2,2‘-bipyridine mono-1,10-phenanthroline ruthenium(II) complexes bearing fused dipyrrolylquinoxaline moieties have been synthesized. As determined by UV−vis spectroscopic and electrochemical studies, these metal complexes bind fluoride with high affinity in polar media both in absolute terms and relative to the metal-free phenanthroline dipyrrolylquinozaline precursor from which they are derived (fluoride is bound to the tris-1,10-phenanthroline cobalt(III) dipyrrolylquinoxaline system with a 1:1 binding constant of 54 000 M-1 in DMSO). The large observed binding constants are ascribed to two factors, (i) the presence of a phenanthroline-coordinated cationic charge that decreases the electron density on the pyrrole NH protons and (ii) pure electrostatic effects.
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phenanthrolineFusedpresenceEfficientcationic54 000 McobaltiitrisdipyrrolylquinozalinemediachargeaffinityDipyrrolylquinoxalinefactormetal complexes bind fluoridepyrrole NH protonsAnionBearingrutheniumspectroscopicComplexeelectron densityFluoridedipyrrolylquinoxaline moietiesPhenanthrolinetermprecursorUVSite54 000electrochemical studiesReceptorbinding constantsDMSONovel anion recognition host moleculesRecognition
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