Inherently Chiral Spider-Like Oligothiophenes

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.