Volume 203, 2017

Comparative study of non-covalent interactions between cationic N-phenylviologens and halides by electrochemistry and NMR: the halogen bonding effect

Abstract

Five N-phenylviologen (PV2+) derivatives have been synthesized and their electrochemical behavior in the presence of halide anions has been studied. Further investigations were carried out by 1H and 19F NMR spectroscopy at different chloride concentrations. This is the first time a systematic study combines cyclic voltammetry and NMR spectroscopy in order to analyse the contribution of halogen bonding among the various non-covalent interactions between iodinated N-phenylviologens. The results show strong evidence for a significant “halogen bonding effect” in the interaction between halides and the iodo-tetrafluoro-phenylviologen PV2+-C6F4I. A significant influence of halogen bonding on reduction potentials of the novel halogen bond donor PV2+-C6F4I has been evidenced resulting in the first example of “inverse redox switching” of an XB-donor being partially deactivated upon reduction. Furthermore the particular binding properties of the perfluorinated derivative PV2+-C6F5 towards chloride are discussed considering a possible contribution of π–anion interaction in solution.

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
26 feb 2017
Accepted
30 mar 2017
First published
30 mar 2017

Faraday Discuss., 2017,203, 301-313

Comparative study of non-covalent interactions between cationic N-phenylviologens and halides by electrochemistry and NMR: the halogen bonding effect

G. Creste, S. Groni, C. Fave, M. Branca and B. Schöllhorn, Faraday Discuss., 2017, 203, 301 DOI: 10.1039/C7FD00082K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements