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Potential‐Driven Chirality Manifestations and Impressive Enantioselectivity by Inherently Chiral Electroactive Organic Films
Author(s) -
Sannicolò Francesco,
Arnaboldi Serena,
Benincori Tiziana,
Bonometti Valentina,
Cirilli Roberto,
Dunsch Lothar,
Kutner Włodzimierz,
Longhi Giovanna,
Mussini Patrizia R.,
Panigati Monica,
Pierini Marco,
Rizzo Simona
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201309585
Subject(s) - chirality (physics) , stereocenter , delocalized electron , chemistry , chemical physics , stereochemistry , materials science , nanotechnology , organic chemistry , enantioselective synthesis , chiral symmetry , physics , catalysis , quantum mechanics , nambu–jona lasinio model , quark
The typical design of chiral electroactive materials involves attaching chiral pendants to an electroactive polyconjugated backbone and generally results in modest chirality manifestations. Discussed herein are electroactive chiral poly‐heterocycles, where chirality is not external to the electroactive backbone but inherent to it, and results from a torsion generated by the periodic presence of atropisomeric, conjugatively active biheteroaromatic scaffolds, (3,3′‐bithianaphthene). As the stereogenic element coincides with the electroactive one, films of impressive chiroptical activity and outstanding enantiodiscrimination properties are obtained. Moreover, chirality manifestations can be finely and reversibly tuned by the electric potential, as progressive injection of holes forces the two thianaphthene rings to co‐planarize to favor delocalization. Such deformations, revealed by CD spectroelectrochemistry, are elastic and reversible, thus suggesting a breathing system.