Helicenes grafted with 1,1,4,4-tetracyanobutadiene moieties pi-helical push-pull systems with strong electronic circular dichroism and two-photon absorption

Romain Bouvier 1 Raphael Durand 1 Ludovic Favereau 1 Monika Srebro-Hooper 2 Vincent Dorcet 1 Thierry Roisnel 1 Nicolas Vanthuyne 3 Yuly Vesga 4 Julie Donnelly 4 Florencio Hernandez 4 Jochen Autschbach 5 Yann Trolez 1 Jeanne Crassous 1
1 ISCR - Institut des Sciences Chimiques de Rennes
2 UJ - Jagiellonian University [Krakow]
3 ISM2 - Institut des Sciences Moléculaires de Marseille
4 University of Central Florida [Orlando]
5 SUNY Buffalo - State University of New York at Buffalo
Abstract : Enantiopure P- and M-carbo[6]helicenes substituted with one or two tetracyanobutadienes in positions 2 and 15 have been prepared. Grafting of these accepting groups on the pi-helical core resulted in strong charge transfer effects which highly affected UV-visible, electronic circular dichroism and two-photon absorption responses. The ECD signal was found to be reversibly switched by applying a redox stimulus.
Keywords : Charge Transfer chiroptical activity helicene tetracyanobutadiene two-photon absorption
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Submitted on : Thursday, August 30, 2018 - 3:09:51 PM
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Romain Bouvier, Raphael Durand, Ludovic Favereau, Monika Srebro-Hooper, Vincent Dorcet, et al.. Helicenes grafted with 1,1,4,4-tetracyanobutadiene moieties pi-helical push-pull systems with strong electronic circular dichroism and two-photon absorption. Chemistry - A European Journal, Wiley-VCH Verlag, 2018, ⟨10.1002/chem.201802763⟩. ⟨hal-01862495⟩

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