6533b83afe1ef96bd12a6f89

RESEARCH PRODUCT

Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides

Hyun Hwa JoElina KaleniusRobin H. A. RasIgor V. KolesnichenkoNgong Kodiah BeyehEric V. AnslynKari RissanenFangfang Pan

subject

chemistry.chemical_classificationta114010405 organic chemistryOrganic ChemistryEnthalpyIsothermal titration calorimetryViologenResorcinarene010402 general chemistry01 natural sciencesviologen derivativesFluorescence spectroscopy0104 chemical scienceschemistry.chemical_compoundN-alkyl ammonium resorcinarene chlorideschemistryPyridinePolymer chemistrymedicineOrganic chemistryAmmoniumta116Alkylmedicine.drug

description

Three water-soluble N-alkyl ammonium resorcinarene chlorides decorated with terminal hydroxyl groups at the lower rims were synthesized and characterized. The receptors were decorated at the upper rim with either terminal hydroxyl, rigid cyclohexyl, or flexible benzyl groups. The binding affinities of these receptors toward three viologen derivatives, two of which possess an acetylmethyl group attached to one of the pyridine nitrogens, in water were investigated via 1H NMR spectroscopy, fluorescence spectroscopy, and isothermal titration calorimetry (ITC). ITC quantification of the binding process gave association constants of up to 103 M–1. Analyses reveal a spontaneous binding process which are all exothermic and are both enthalpy and entropy driven.

yearjournalcountryeditionlanguage
2017-01-01JOURNAL OF ORGANIC CHEMISTRY
10.1021/acs.joc.7b00449https://doi.org/10.1021/acs.joc.7b00449