Helicenes Grafted with 1,1,4,4‐Tetracyanobutadiene Moieties: π‐Helical Push–Pull Systems with Strong Electronic Circular Dichroism and Two‐Photon Absorption

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 circ...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-09, Vol.24 (54), p.14484-14494
Main Authors: Bouvier, Romain, Durand, Raphaël, Favereau, Ludovic, Srebro‐Hooper, Monika, Dorcet, Vincent, Roisnel, Thierry, Vanthuyne, Nicolas, Vesga, Yuly, Donnelly, Julie, Hernandez, Florencio, Autschbach, Jochen, Trolez, Yann, Crassous, Jeanne
Format: Article
Language:English
Subjects:
Absorption
Charge transfer
Chemical Sciences
Chemistry
chiroptical activity
Circular dichroism
Dichroism
helicenes
Photon absorption
tetracyanobutadiene
two-photon absorption
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Summary: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. π‐Helical push–pull systems: Examples of a new type of π‐helical push–pull molecules have been prepared, consisting of helicene grafted with tetracyanobutadiene moieties as electron‐accepting substituents.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201802763