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Chemphyschem. 2015 Oct 26;16(15):3325-33. doi: 10.1002/cphc.201500473. Epub 2015 Aug 25.

Triphilic Ionic-Liquid Mixtures: Fluorinated and Non-fluorinated Aprotic Ionic-Liquid Mixtures.

Author information

1
Mulliken Center for Theoretical Chemistry, Rheinische Friedrich-Wilhelms-Universität Bonn, Beringstr. 4+6, 53115, Bonn, Germany.
2
Helmholtz-Zentrum für Umweltforschung Leipzig, Department Ökologische Chemie, Permoserstrasse 15, 04318, Leipzig, Germany.
3
SMRI Sugarcane Biorefinery Research Chair, University of KwaZulu-Natal, College of Agriculture, Engineering and Science School of Engineering, Howard College Campus, Durban, South Africa.
4
Department of Chemistry, Sapienza University of Rome, 00185, Rome, Italy.
5
Laboratorio Liquidi Ionici, Istituto Struttura della Materia, Consiglio Nazionale delle Ricerche, 00133, Rome, Italy.
6
Mulliken Center for Theoretical Chemistry, Rheinische Friedrich-Wilhelms-Universität Bonn, Beringstr. 4+6, 53115, Bonn, Germany. kirchner@thch.uni-bonn.de.

Abstract

We present here the possibility of forming triphilic mixtures from alkyl- and fluoroalkylimidazolium ionic liquids, thus, macroscopically homogeneous mixtures for which instead of the often observed two domains-polar and nonpolar-three stable microphases are present: polar, lipophilic, and fluorous ones. The fluorinated side chains of the cations indeed self-associate and form domains that are segregated from those of the polar and alkyl domains. To enable miscibility, despite the generally preferred macroscopic separation between fluorous and alkyl moieties, the importance of strong hydrogen bonding is shown. As the long-range structure in the alkyl and fluoroalkyl domains is dependent on the composition of the liquid, we propose that the heterogeneous, triphilic structure can be easily tuned by the molar ratio of the components. We believe that further development may allow the design of switchable, smart liquids that change their properties in a predictable way according to their composition or even their environment.

KEYWORDS:

ionic liquids; microphases; molecular dynamics; nanosegregation fluorination; simulations microheterogen

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