Introducing inherent chirality in electrochemistry : new electrode surfaces with outstanding enantiorecognition properties and new-concept chiral ionic liquids
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Data di Pubblicazione:
2014
Citazione:
Introducing inherent chirality in electrochemistry : new electrode surfaces with outstanding enantiorecognition properties and new-concept chiral ionic liquids / F. Sannicolò, P.R. Mussini, S. Arnaboldi, S. Riva, E. Lo Bello, V. Marino, T. Benincori, S. Rizzo, V. Mihali, A. Gennaro, A.A. Isse. ((Intervento presentato al 10. convegno ECHEMS Meeting : Electrochemistry in molecular understanding tenutosi a Wells (Somerset, UK) nel 2014.
Abstract:
The typical design of chiral electroactive materials involves attaching chiral pendants to an
electroactive polyconjugated backbone and generally results in modest chirality manifestations. We have
designed "inherently chiral" thiophene-based electroactive monomers, where chirality is not external to
the electroactive backbone but inherent to it, and results from a torsion generated by the presence of an
atropisomeric, conjugatively active biheteroaromatic scaffold. The coincidence of the stereogenic element
with the whole electroactive backbone in the starting monomers affords by electrooligomerization
enantiopure electrode surfaces with impressive chiroptical activity, finely and reversibly tunable by the
electric potential, and with outstanding enantiorecognition ability towards specular redox probes [1].
Besides extending such exciting study, we are now 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 number,
position and length of alkyl chain substituents.
With the contribution of Fondazione Cariplo, grants no. 2011-0417 (inherently chiral electrodes) and no.
2011-1851 (inherently chiral ionic liquids)
References
[1] F. Sannicolò, S. Arnaboldi, T. Benincori, V. Bonometti, R. Cirilli, L. Dunsch, W. Kutner, G. Longhi,
P.R. Mussini, M. Panigati, M. Pierini, S. Rizzo, Angew. Chem. 2014, 53, 2623-2627.
Tipologia IRIS:
14 - Intervento a convegno non pubblicato
Keywords:
chiral electroactive materials ; enantioselective electrodes ; chiral ionic liquids ; chiral electroactive cyclic oligothiophenes
Elenco autori:
F. Sannicolò, P.R. Mussini, S. Arnaboldi, S. Riva, E. Lo Bello, V. Marino, T. Benincori, S. Rizzo, V. Mihali, A. Gennaro, A.A. Isse
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