The Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides
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.
Main Authors
Format
Articles
Research article
Published
2017
Series
Subjects
Publication in research information system
Publisher
American Chemical Society
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-201705232461Käytä tätä linkitykseen.
Review status
Peer reviewed
ISSN
0022-3263
DOI
https://doi.org/10.1021/acs.joc.7b00449
Language
English
Published in
Journal of Organic Chemistry
Citation
- Beyeh, N. K., Jo, H. H., Kolesnichenko, I., Pan, F., Kalenius, E., Anslyn, E. V., Ras, R. H. A., & Rissanen, K. (2017). The Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides. Journal of Organic Chemistry, 82(10), 5198-5203. https://doi.org/10.1021/acs.joc.7b00449
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Funder(s)
Research Council of Finland
Research Council of Finland
Research Council of Finland
Research Council of Finland
Funding program(s)
Akatemiatutkija, SA
Akatemiaprofessorin tehtävä, SA
Akatemiatutkijan tutkimuskulut, SA
Akatemiaprofessorin tutkimuskulut, SA
Academy Research Fellow, AoF
Research post as Academy Professor, AoF
Research costs of Academy Research Fellow, AoF
Research costs of Academy Professor, AoF
Additional information about funding
The authors gratefully acknowledge financial support from the Academy of Finland (K.R.: Grant Nos. 265328, 263256, and 292746; N.K.B.: Grant No. 258653; R.H.A.R.: Grant No. 272579; E.K.: Grant Nos. 284562 and 278743), Aalto University, the University of Jyvaskyla Finland, Central China Normal University and National Science Foundation (E.V.A.: Grant CHE-1212971), and the Welch Regents Chair (E.V.A.: F-0046).
Copyright© 2017 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by ACS. Published in this repository with the kind permission of the publisher.