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Inherently Chiral Spider‐Like Oligothiophenes |
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| Authors: | Prof. Francesco Sannicolò Prof. Patrizia R. Mussini Prof. Tiziana Benincori Prof. Rocco Martinazzo Dr. Serena Arnaboldi Giulio Appoloni Dr. Monica Panigati Dr. Elsa Quartapelle Procopio Valentina Marino Dr. Roberto Cirilli Dr. Simone Casolo Prof. Wlodzimierz Kutner Dr. Krzysztof Noworyta Dr. Agnieszka Pietrzyk‐Le Zofia Iskierko Katarzyna Bartold |
| Affiliation: | 1. Dipartimento di Chimica, Università degli Studi di Milano, Milano, Italy;2. Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Como, Italy;3. Dipartimento del Farmaco, Istituto Superiore di Sanità, Roma, Italy;4. Institute of Physical Chemistry, Polish Academy of Sciences, Warsaw, Poland |
| 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. |
| Keywords: | chirality enantiorecognition hyperbranching molecularly imprinted polymers oligothiophenes |