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Helicenes Grafted with 1,1,4,4‐Tetracyanobutadiene Moieties: π‐Helical Push–Pull Systems with Strong Electronic Circular Dichroism and Two‐Photon Absorption
Author(s) -
Bouvier Romain,
Durand Raphaël,
Favereau Ludovic,
SrebroHooper Monika,
Dorcet Vincent,
Roisnel Thierry,
Vanthuyne Nicolas,
Vesga Yuly,
Donnelly Julie,
Hernandez Florencio,
Autschbach Jochen,
Trolez Yann,
Crassous Jeanne
Publication year - 2018
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.201802763
Subject(s) - circular dichroism , enantiopure drug , two photon absorption , absorption (acoustics) , photochemistry , redox , magnetic circular dichroism , electron transfer , materials science , chemistry , crystallography , optics , physics , organic chemistry , enantioselective synthesis , spectral line , laser , composite material , catalysis , astronomy
Enantiopure P ‐ and M ‐carbo[6]helicenes substituted with one or two tetracyanobutadiene moieties at positions 2 and 15 have been prepared. Grafting of these electron‐accepting groups onto the π‐helical core resulted in strong charge‐transfer effects, which greatly affected the UV/Vis, electronic circular dichroism (ECD), and two‐photon absorption (TPA) responses. The ECD signal was found to be reversibly switched by applying a redox stimulus.