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

Romain Bouvier; Raphaël Durand; Ludovic Favereau; Monika Srebro-Hooper; Vincent Dorcet; Thierry Roisnel; Nicolas Vanthuyne; Yuly Vesga; Julie Donnelly; Florencio Hernandez; Jochen Autschbach; Yann Trolez; Jeanne Crassous

doi:10.1002/chem.201802763

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

Romain Bouvier
, Raphaël Durand
, Ludovic Favereau
, Monika Srebro-Hooper
, Vincent Dorcet
, Thierry Roisnel
, Nicolas Vanthuyne
, Yuly Vesga
, Julie Donnelly
, Florencio Hernandez
, Jochen Autschbach
, Yann Trolez
, Jeanne Crassous

Chemistry

Université de Rennes
Jagiellonian University in Kraków
Aix Marseille University
University of Central Florida

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	14484-14494
Number of pages	11
Journal	Chemistry - A European Journal
Volume	24
Issue number	54
DOIs	https://doi.org/10.1002/chem.201802763
State	Published - Sep 25 2018

Keywords

charge transfer
chiroptical activity
helicenes
tetracyanobutadiene
two-photon absorption

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10.1002/chem.201802763

Cite this

Bouvier, R., Durand, R., Favereau, L., Srebro-Hooper, M., Dorcet, V., Roisnel, T., Vanthuyne, N., Vesga, Y., Donnelly, J., Hernandez, F., Autschbach, J., Trolez, Y., & Crassous, J. (2018). Helicenes Grafted with 1,1,4,4-Tetracyanobutadiene Moieties: π-Helical Push–Pull Systems with Strong Electronic Circular Dichroism and Two-Photon Absorption. Chemistry - A European Journal, 24(54), 14484-14494. https://doi.org/10.1002/chem.201802763

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

abstract = "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.",

keywords = "charge transfer, chiroptical activity, helicenes, tetracyanobutadiene, two-photon absorption",

author = "Romain Bouvier and Rapha{\"e}l Durand and Ludovic Favereau and Monika Srebro-Hooper and Vincent Dorcet and Thierry Roisnel and Nicolas Vanthuyne and Yuly Vesga and Julie Donnelly and Florencio Hernandez and Jochen Autschbach and Yann Trolez and Jeanne Crassous",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = sep,

day = "25",

doi = "10.1002/chem.201802763",

language = "English",

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Bouvier, R, Durand, R, Favereau, L, Srebro-Hooper, M, Dorcet, V, Roisnel, T, Vanthuyne, N, Vesga, Y, Donnelly, J, Hernandez, F, Autschbach, J, Trolez, Y & Crassous, J 2018, 'Helicenes Grafted with 1,1,4,4-Tetracyanobutadiene Moieties: π-Helical Push–Pull Systems with Strong Electronic Circular Dichroism and Two-Photon Absorption', Chemistry - A European Journal, vol. 24, no. 54, pp. 14484-14494. https://doi.org/10.1002/chem.201802763

Helicenes Grafted with 1,1,4,4-Tetracyanobutadiene Moieties: π-Helical Push–Pull Systems with Strong Electronic Circular Dichroism and Two-Photon Absorption. / Bouvier, Romain; Durand, Raphaël; Favereau, Ludovic et al.
In: Chemistry - A European Journal, Vol. 24, No. 54, 25.09.2018, p. 14484-14494.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Helicenes Grafted with 1,1,4,4-Tetracyanobutadiene Moieties

T2 - π-Helical Push–Pull Systems with Strong Electronic Circular Dichroism and Two-Photon Absorption

AU - Bouvier, Romain

AU - Durand, Raphaël

AU - Favereau, Ludovic

AU - Srebro-Hooper, Monika

AU - Dorcet, Vincent

AU - Roisnel, Thierry

AU - Vanthuyne, Nicolas

AU - Vesga, Yuly

AU - Donnelly, Julie

AU - Hernandez, Florencio

AU - Autschbach, Jochen

AU - Trolez, Yann

AU - Crassous, Jeanne

PY - 2018/9/25

Y1 - 2018/9/25

N2 - 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.

AB - 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.

KW - charge transfer

KW - chiroptical activity

KW - helicenes

KW - tetracyanobutadiene

KW - two-photon absorption

UR - https://www.scopus.com/pages/publications/85053415861

U2 - 10.1002/chem.201802763

DO - 10.1002/chem.201802763

M3 - Article

C2 - 29995309

AN - SCOPUS:85053415861

SN - 0947-6539

VL - 24

SP - 14484

EP - 14494

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 54

ER -

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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