Inherently chiral conducting polymer electrodes 

Patrizia R. Mussini 1Francesco Sannicolò 2Valentina Bonometti 1Ester Giussani 1Wlodzimierz Kutner 3Krzysztof R. Noworyta 3Tiziana Benincori 4Simona Rizzo 5Roberto Cirilli 6Monica Panigati 7Sergio Abbate 8Giovanna Longhi 8Ettore Castiglioni 9

1. Università di Milano, Dipartimento di Chimica Fisica ed Elettrochimica, via Golgi, 19, Milano 20133, Italy
2. Università degli Studi di Milano, Dipartimento di Chimica Organica e Industriale, via Venezian 21, Milano 20133, Italy
3. Polish Academy of Sciences, Institute of Physical Chemistry, Kasprzaka 44/52, Warszawa 01-224, Poland
4. Università dell'Insubria, Dipartimento di Scienze Chimiche e Ambientali, via Valleggio 11, Como 22100, Italy
5. ISTM-CNR, Via C. Colgi 19, Milano 20133, Italy
6. Department of Therapeutic Research and Medicines Evaluation, Italian National Institute of Health, Viale Regina Elena 299, Roma 00161, Italy
7. Università degli Studi di Milano Dipartimento di Chimica Inorganica, Metallorganica e Analitica, Via Venezian 21, Milano 20133, Italy
8. Dipartimento di Scienze Biomediche e Biotecnologie, Università di Brescia, Viale Europa 11, Brescia 25123, Italy
9. Jasco Europe, Via Cadorna 1, Cremella 23894, Italy

Abstract

 The availability of materials able to couple electroactivity and enantio­re­cog­ni­tion capability is an ambitious objective of the current chemical research, aiming to both elec­tri­cally triggered enantioselective electron transfers and electri­cally moni­tored enantio­selective recognitions. Ideal candidates are organic con­duct­ing poly­mers, several of which have been functionalized with chiral pendants; this "loca­lized" approach, however, appears to lead to poor chirality manifestations. We present inherently chiral conducting films pre­pared by electropolymerization of monomers like the TBTX mole­cu­le in the figure, where chirality is owed to a tailored torsion in­­ter­nally pro­duced along the whole conjugated back­bone, and not to the presence of stereocentres external to the conjugated chain. Both enantio­mer films have been characterized together with the racemate one by CV, EIS, and circular di­chro­ism with in-situ electrochemistry. Positive charge in­jec­tion, reducing the torsion angle to achieve better π system conjugation, results in a fully rever­sible "breath­ing" process of the 3D chiral con­duct­ing net­­­work upon po­tential cy­cling. Enan­tio­re­cog­nition ca­pa­bi­lity tests on chiral probe molecules are in progress.

 

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Presentation: Short communication at SMCBS'2011 International Workshop, by Patrizia R. Mussini
See On-line Journal of SMCBS'2011 International Workshop

Submitted: 2011-09-06 10:03
Revised:   2011-09-06 10:39