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Chiroptical Properties of Carbo[6]Helicene Derivatives Bearing Extended π‐Conjugated Cyano Substituents
Author(s) -
Moussa Mehdi El Sayed,
Srebro Monika,
Anger Emmanuel,
Vanthuyne Nicolas,
Roussel Christian,
Lescop Christophe,
Autschbach Jochen,
Crassous Jeanne
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22201
Subject(s) - helicene , enantiopure drug , chemistry , chirality (physics) , conjugated system , circular dichroism , optical rotation , molecule , spectroscopy , molar ratio , computational chemistry , stereochemistry , organic chemistry , polymer , enantioselective synthesis , chiral symmetry , quark , physics , quantum mechanics , nambu–jona lasinio model , catalysis
New carbo[6]helicene derivatives grafted with π‐conjugated cyano‐phenyl arms were synthesized in enantiopure forms and their π‐conjugation examined by UV–vis spectroscopy. The influence of the π‐conjugation on the circular dichroism spectra and molar rotations is discussed based on comparing experimental data with results from quantum‐chemical calculations. The results highlight the fact that increasing the spatial extension of the π‐system in a helicene molecule is an efficient way of increasing its molar rotation. Chirality 25:455–465, 2013 . © 2013 Wiley Periodicals, Inc.