Towards inherently chiral Ionic liquids: molecular design strategies and electrochemical properties
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Data di Pubblicazione:
2014
Citazione:
Towards inherently chiral Ionic liquids: molecular design strategies and electrochemical properties / P.R. Mussini, F. Sannicolò, S. Rizzo, S. Arnaboldi, V. Mihali, A. Gennaro, A.A. Isse. ((Intervento presentato al 65. convegno Annual Meeting of the International Society of Electrochemistry tenutosi a Lausanne nel 2014.
Abstract:
Chiral Ionic Liquids (CILs) constitute a class of chiral solvents of steadily increasing
importance in the last years; they are employed inter alia as chiral solvents for
asymmetric synthesis and stereoselective polymerization, as chiral phases in gas
chromatography and as chiral shift reagents in NMR spectroscopy. Although their
application to electrochemical processes is a field still requiring exploration, they
should have a huge impact for instance in asymmetric electropolymerizations and in
regioregular electrochemically activated polymerizations, as well as in preparative
electrosynthetic processes of chiral compounds.
The current general design of CILs follows rather intuitive strategies. The use of a
chiral anion (e.g. from lactic acid, -aminoacids, 10-camphorsulfonic acid, 1,1’-
binaphthylphosphoric acid) is a simple but scarcely innovative strategy. More
possibilities are afforded by the chiral cation approach; in this case a wide range of
building blocks have been so far explored to confer chirality, from the classical 1-
phenylethyl group to derivatives of tartaric acid, pinene, myrtanol, citronellol, menthol,
carvone, etc.
Our group has recently proposed electroactive thiophene-based polyconjugated films of
unprecedented chirality manifestations and enantiorecognition ability[1] based on the
concept of the whole electroactive backbone coinciding with the stereogenic element,
consisting in a tailored torsion induced by an atropisomeric bithiophene scaffold. Now
we are trying to apply the same "inherent chirality" approach to the development of
inherently chiral ionic liquids, hopefully endowed with high enantioselectivity, like the
formerly developed inherently chiral electrodes. An overview will be given of the first
structures obtained and of their electrochemical properties. The new molecules are
based on cations including different atropisomeric bis-benzimidazolium groups acting
as the stereogenic element, responsible for both the molecular chirality and the IL
properties of the material, modulated by the number, position and length of alkyl chain
substituents.
Tipologia IRIS:
14 - Intervento a convegno non pubblicato
Elenco autori:
P.R. Mussini, F. Sannicolò, S. Rizzo, S. Arnaboldi, V. Mihali, A. Gennaro, A.A. Isse
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