Data di Pubblicazione:
2013
Citazione:
Enantioselective electrodes based on inherently chiral molecular materials / S. Arnaboldi, T. Benincori, V. Bonometti, R. Cirilli, L. Dunsch, W. Kutner, G. Longhi, K. Noworyta, P.R. Mussini, M. Panigati, M. Pierini, S. Rizzo, F. Sannicolò. ((Intervento presentato al convegno Giornata del Gruppo Sensori della Società Chimica Italiana e della Società Italiana di Ottica e Fotonica tenutosi a Sestri Levante nel 2013.
Abstract:
The availability of materials coupling electroactivity with enantiorecognition
capability is an attractive objective in materials research. The usual strategy,
hinging on attaching chiral pendants to an electroactive polyconjugated backbone,
generally results in modest chirality manifestations. We have thus designed
electroactive chiral polyheterocycles, where chirality is not external to the
electroactive backbone, but inherent to it, resulting from a tailored torsion produced
by the periodical presence of atropisomeric, conjugatively active biheteroaromatic
scaffolds. This affords enantiopure electroactive films of impressive
chiroptical activity; moreover, since the stereogenic element coincides with
the electroactive site, chirality manifestations can be finely and reversibly tuned
by the electric potential, since progressive injection of positive charges forces
the atropisomeric scaffold angle to regularly decrease to favour delocalization.
Such deformations are elastic and reversible (CD spectroelectrochemistry).
In order to test the enantiorecognition ability of the new enantiomeric
electrodes, we have in the last months developed a protocol in ionic liquid medium
affording preparation of very reproducible electrode surfaces on screen
printed electrode supports. The resulting specular
R and S electrodes have been tested in the
presence of (R)-(+)- and S-( )-N,N-dimethyl-1-
ferrocenylethylamine specular probes. The response
is highly and reproducibly enantioselective
(with even more than 100 mV separation
between R and S probes, either with single
enantiomers and with the racemate), specular
for R vs S surfaces with respect to S and R
probes, and reversible in repeated alternating sequences
of S and R probe sensing on a single electrode.
Tipologia IRIS:
14 - Intervento a convegno non pubblicato
Elenco autori:
S. Arnaboldi, T. Benincori, V. Bonometti, R. Cirilli, L. Dunsch, W. Kutner, G. Longhi, K. Noworyta, P.R. Mussini, M. Panigati, M. Pierini, S. Rizzo, F. Sannicolò
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