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.
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milano, Italy.
Francesco
F
Sannicolò
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milano, Italy. patrizia.mussini@unimi.it.
Patrizia R
PR
Mussini
Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Via Valleggio 11, 22100, Como, Italy. tiziana.benincori@uninsubria.it.
Tiziana
http://orcid.org/0000-0001-6903-7440
T
Benincori
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milano, Italy. rocco.martinazzo@unimi.it.
Rocco
R
Martinazzo
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milano, Italy.
Serena
S
Arnaboldi
Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Via Valleggio 11, 22100, Como, Italy.
Giulio
G
Appoloni
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milano, Italy.
Monica
M
Panigati
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milano, Italy.
Elsa
E
Quartapelle Procopio
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milano, Italy.
Valentina
V
Marino
Dipartimento del Farmaco, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161, Roma, Italy.
Roberto
R
Cirilli
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milano, Italy.
Simone
S
Casolo
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Wlodzimierz
W
Kutner
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Krzysztof
K
Noworyta
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Agnieszka
A
Pietrzyk-Le
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Zofia
Z
Iskierko
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Katarzyna
K
Bartold
D002942:Circular Dichroism; D008958:Models, Molecular; D054802:Molecular Imprinting / Q000379:methods*; D013237:Stereoisomerism; D013876:Thiophenes / Q000737:chemistry*
D013876:Thiophenes
chirality; enantiorecognition; hyperbranching; molecularly imprinted polymers; oligothiophenes