Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides
Kari Rissanen, Ngong Kodiah Beyeh, Hyun Hwa Jo, Eric V. Anslyn, Fangfang Pan, Igor Kolesnichenko, Robin H. A. Ras, Elina Kalenius
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00449

DOI: 10.1021/acs.joc.7b00449

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