Issue 8, 2010
From the journal:

Physical Chemistry Chemical Physics

Solid and liquid charge-transfer complex formation between 1-methylnaphthalene and 1-alkyl-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide ionic liquids†

Christopher Hardacre,a   John D. Holbrey,a   Claire L. Mullan,a   Mark Nieuwenhuyzen,a   Tristan G. A. Youngs,a   Daniel T. Bowronb  and  Simon J. Teatc  

a School of Chemistry and Chemical Engineering/School of Mathematics and Physics, The QUILL Centre, Queen’s University Belfast, Belfast, UK
E-mail: c.hardacre@qub.ac.uk
Fax: +44 28 9097 4687
Tel: +44 28 9097 4592

b Rutherford Appleton Laboratory, Chilton, Didcot, Oxon, UK

c Advanced Light Source, Lawrence Berkeley National Lab, 1 Cyclotron Rd, Berkeley, USA

Abstract

Liquid charge-transfer (CT) complexes were observed to form on contacting electron-rich aromatics with electron withdrawing group appended 1-alkyl-4-cyanopyridinium ionic liquids (ILs). Cooling below the melting point of the ionic liquid resulted in crystallisation of ionic liquid from the complex for 2-cyano and 3-cyano pyridinium isomers and in the formation of a 1 : 1 IL : aromatic crystalline CT-complex with the 4-cyanopyridinium isomer. The liquid structure of a 1 : 1 mixture of 1-methyl-4-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide with 1-methylnaphthalene has been probed by neutron diffraction experiments and molecular dynamics simulations. A high degree of correlation between the experimental data and the simulations was found with a significant displacement of the anions from around the cation by the aromatic species and the resulting structure having π–π stacks between the cations and the aromatic.

Graphical abstract: Solid and liquid charge-transfer complex formation between 1-methylnaphthalene and 1-alkyl-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide ionic liquids

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Article information

DOI
https://doi.org/10.1039/B921160H
Article type
Paper
Submitted
12 Oct 2009
Accepted
14 Dec 2009
First published
18 Jan 2010

Phys. Chem. Chem. Phys., 2010,12, 1842-1853

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Solid and liquid charge-transfer complex formation between 1-methylnaphthalene and 1-alkyl-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide ionic liquids

C. Hardacre, J. D. Holbrey, C. L. Mullan, M. Nieuwenhuyzen, T. G. A. Youngs, D. T. Bowron and S. J. Teat, Phys. Chem. Chem. Phys., 2010, 12, 1842 DOI: 10.1039/B921160H

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