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.

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 T83racemate 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.

Inherently Chiral Spider-Like Oligothiophenes

BENINCORI, TIZIANA;APPOLONI, GIULIO;
2016-01-01

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 T83racemate 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.
2016
chirality; enantiorecognition; hyperbranching; molecularly imprinted polymers; oligothiophenes;
Sannicolo, Francesco; Mussini, Patrizia R; Benincori, Tiziana; Martinazzo, Rocco; Arnaboldi, Serena; Appoloni, Giulio; Panigati, Monica; Quartapelle Procopio, Elsa; Marino, Valentina; Cirilli, Roberto; Casolo, Simone; Noworyta, Krzysztof; Pietrzyk Le, Agnieszka; Iskierko, Zofia; Bartold, Katarzyna
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2060053
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