Helitwistacenes—Combining Lateral and Longitudinal Helicity Results in Solvent-Induced Inversion of Circularly Polarized Light

Israa Shioukhi, Harikrishna Batchu, Gal Schwartz, Louis Minion, Yinon Deree, Benny Bogoslavsky, Linda J.W. Shimon, Jessica Wade, Roy Hoffman, Matthew J. Fuchter, Gil Markovich, Ori Gidron*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Helicity is expressed differently in ortho- and para-fused acenes—helicenes and twistacenes, respectively. While the extent of helicity is constant in helicenes, it can be tuned in twistacenes, and the handedness of flexible twistacenes is often determined by more rigid helicenes. Here, we combine helicenes with rigid twistacenes consisting of a tunable degree of twisting, forming helitwistacenes. While the X-ray structures reveal that the connection does not affect the helicity of each moiety, their electronic circular dichroism (ECD) and circularly polarized luminescence (CPL) spectra are strongly affected by the helicity of the twistacene unit, resulting in solvent-induced sign inversion. ROESY NMR and TD-DFT calculations support this observation, which is explained by differences in the relative orientation of the helicene and twistacene moieties.

Original languageAmerican English
JournalAngewandte Chemie - International Edition
Early online date15 Jan 2024
DOIs
StateE-pub ahead of print - 15 Jan 2024

Bibliographical note

Publisher Copyright:
© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Keywords

  • Chirality
  • Circular Dichroism
  • Circularly Polarized Luminescence
  • Helicenes
  • Twistacenes

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