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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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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cited_by cdi_FETCH-LOGICAL-c4473-e36bd413d6669f2f7f5d09fc2f54452449ba338878f86c8d038cfc7a8b73733e3
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container_issue 54
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creator 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
description 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.
doi_str_mv 10.1002/chem.201802763
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subjects Absorption
Charge transfer
Chemical Sciences
Chemistry
chiroptical activity
Circular dichroism
Dichroism
helicenes
Photon absorption
tetracyanobutadiene
two-photon absorption
title Helicenes Grafted with 1,1,4,4‐Tetracyanobutadiene Moieties: π‐Helical Push–Pull Systems with Strong Electronic Circular Dichroism and Two‐Photon Absorption
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