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Inherently Chiral Spider‐Like Oligothiophenes
Author(s) -
Sannicolò Francesco,
Mussini Patrizia R.,
Benincori Tiziana,
Martinazzo Rocco,
Arnaboldi Serena,
Appoloni Giulio,
Panigati Monica,
Quartapelle Procopio Elsa,
Marino Valentina,
Cirilli Roberto,
Casolo Simone,
Kutner Wlodzimierz,
Noworyta Krzysztof,
PietrzykLe Agnieszka,
Iskierko Zofia,
Bartold Katarzyna
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504899
Subject(s) - spider , enantiomer , monomer , chirality (physics) , oligonucleotide , chemistry , stereochemistry , combinatorial chemistry , polymer , organic chemistry , dna , chiral symmetry , biology , zoology , biochemistry , nambu–jona lasinio model , physics , quantum mechanics , quark
The racemate of an inherently chiral “spider‐like” octathiophene monomer T8 3 , 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 T8 3 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.