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

Ngong K. Beyeh, Hyun Hwa Jo, Igor Kolesnichenko, Fangfang Pan, Elina Kalenius, Eric V. Anslyn, Robin H. A. Ras, Kari Rissanen

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7 Citations (Scopus)

Abstract

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.
Original languageEnglish
Article number10
Pages (from-to)5198–5203
JournalJournal of organic chemistry
Volume82
Issue number10
DOIs
Publication statusPublished - 28 Apr 2017
MoE publication typeA1 Journal article-refereed

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    Beyeh, N. K., Jo, H. H., Kolesnichenko, I., Pan, F., Kalenius, E., Anslyn, E. V., ... Rissanen, K. (2017). Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides. Journal of organic chemistry, 82(10), 5198–5203. [10]. https://doi.org/10.1021/acs.joc.7b00449