4.6 Article

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

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 54, Pages 14484-14494

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201802763

Keywords

charge transfer; chiroptical activity; helicenes; tetracyanobutadiene; two-photon absorption

Funding

  1. Ministere de l'Education Nationale, de la Recherche et de la Technologie
  2. Centre National de la Recherche Scientifique (CNRS)
  3. University of Rennes 1
  4. Ecole Nationale Superieure de Chimie de Rennes
  5. Ministry of Science and Higher Education in Poland
  6. National Science Foundation [CHE-1560881]

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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 pi-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.

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