Volume 22, Issue 31 p. 10839-10847
Full Paper

Inherently Chiral Spider-Like Oligothiophenes

Prof. Francesco Sannicolò

Prof. Francesco Sannicolò

Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

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Prof. Patrizia R. Mussini

Corresponding Author

Prof. Patrizia R. Mussini

Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

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Prof. Tiziana Benincori

Corresponding Author

Prof. Tiziana Benincori

Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Via Valleggio 11, 22100 Como, Italy

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Prof. Rocco Martinazzo

Corresponding Author

Prof. Rocco Martinazzo

Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

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Dr. Serena Arnaboldi

Dr. Serena Arnaboldi

Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

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Giulio Appoloni

Giulio Appoloni

Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Via Valleggio 11, 22100 Como, Italy

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Dr. Monica Panigati

Dr. Monica Panigati

Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

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Dr. Elsa Quartapelle Procopio

Dr. Elsa Quartapelle Procopio

Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

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Valentina Marino

Valentina Marino

Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

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Dr. Roberto Cirilli

Dr. Roberto Cirilli

Dipartimento del Farmaco, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161 Roma, Italy

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Dr. Simone Casolo

Dr. Simone Casolo

Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

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Prof. Wlodzimierz Kutner

Prof. Wlodzimierz Kutner

Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

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Dr. Krzysztof Noworyta

Dr. Krzysztof Noworyta

Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

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Dr. Agnieszka Pietrzyk-Le

Dr. Agnieszka Pietrzyk-Le

Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

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Zofia Iskierko

Zofia Iskierko

Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

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Katarzyna Bartold

Katarzyna Bartold

Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

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First published: 20 June 2016
Citations: 25

Graphical Abstract

Hyperbranched oligothiophenes display outstanding physicochemical properties. Hindered rotation around some specific interannular bonds provides these systems with additional relevant attributes: inherent chirality and high framework stiffness. The former endows the molecules with chiral discrimination properties, the latter with the unfading memory of templating species.

Abstract

The racemate of an inherently chiral “spider-like” octathiophene monomer T83, in which chirality is generated by torsion in its backbone, was synthesized. The racemate was resolved into configurationally stable antipodes by HPLC on a chiral stationary phase. Electrooxidation of the enantiomers resulted in materials displaying high enantiorecognition ability towards the antipodes of some chiral probes. Moreover, the T83 racemate demonstrated great aptitude to stimulate formation of 3D rigid architectures if used as a cross-linking monomer for molecular imprinting. This feature was exploited to devise a molecularly imprinted polymer-based chemosensor selective for a thymine–adenine oligonucleotide.