AZOLIUM-BASED SYSTEMS: APPLICATION OF AN ANION EXCHANGE RESIN (A¯ FORM) METHOD
Neus Mesquida, Immaculada Dinarès, Anna Ibáñez and Ermitas Alcalde
Pharmacology and Therapeutic Chemistry, Universitat de Barcelona, Spain
Abstract:
Azolium systems have gained a place among the anion-binding functional groups, ranging from
anion receptors and sensors to transporters, and as ionic liquids (ILs) their utility has expanded into
domains beyond chemistry. The chemical aspects of imidazolium-based ILs, including their
synthesis, counteranion exchange and purity, have been the subject of numerous studies with the aim
of obtaining pure IL salts, especially halide-free ion pairs [1-3]. We have recently examined the
preparation of an anion exchange resin (A¯form) conveniently loaded with a selected anion after
treatment with either acids or ammonium salts in water, or hydroalcoholic media, or organic solvents [4]. The present
study is focused on the application of the AER (A¯form) method for the halide-to-anion exchan ge of selected
triazolium ion pairs. Additionally, a strong basic AER (N3¯form) was used to obtain the benzyl azide compone nt from
benzyl halide under mild reaction conditions. Following a similar protocol, bis(azidomethyl) arenes were also
synthesized in excellent yields.
Acknowledgments: The authors thank to the SCT-UB for the use of their instruments and the AGAUR (Generalitat de
Catalunya), Grup de Recerca Consolidat 2009SGR562.
REFERENCES:
[1] E. Alcalde, I. Dinarès, N. Mesquida. Top. Heterocycl. Chem., 2010, 24, 267–300.
[2] A. E. Hargrove, S. Nieto, T. Zhang, J. L. Sessler, E. V. Anslyn. Chem. Rev., 2011, 111, 6603–6782.
[3] M. Wenzel, J. R. Hiscock, P. A. Gale. Chem. Soc. Rev., 2012, 41, 480–520.
[4] E. Alcalde, I. Dinarès, A. Ibáñez, N. Mesquida. Molecules 2012, 17, 4007–4027.
