Chiroptical Properties of Twisted Acenes: Experimental and Computational Study

Anjan Bedi, Ori Gidron

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

Acenes that are twisted out of planarity are expected to display chiroptical properties. However, the effect of twisting on the chiroptical properties of acenes has not been investigated computationally or experimentally. Herein, we present a computational investigation of the chiroptical properties of anthracenes to pentacenes, combined with an experimental study using a series of helically locked acenes, twisted to different torsional angles in their enantiopure form. The lowest energy transition, which is relatively weak in acenes, becomes dominant in their circular dichroism spectra upon twisting. We find that the rotational strength of acenes consistently increases with increasing twist. The experimental data obtained from enantiopure tethered twistacenes show the same trend as the calculated result, with a strong Cotton effect and anisotropy factor, rendering twisted acenes as excellent chiroptical materials.

Original languageAmerican English
Pages (from-to)3279-3285
Number of pages7
JournalChemistry - A European Journal
Volume25
Issue number13
DOIs
StatePublished - 1 Mar 2019

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

  • acenes
  • chiroptical properties
  • circular dichroism
  • cyclophanes
  • twistacenes

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