Circularly Polarized Luminescence in a Möbius Helicene Carbon Nanohoop

Angew Chem Int Ed Engl. 2022 Sep 12;61(37):e202208591. doi: 10.1002/anie.202208591. Epub 2022 Aug 4.

Abstract

We present the first helicene carbon nanoohop that integrates a [6]helicene into [7]cycloparaphenylene. The [6]helicene endows the helicene carbon nanohoop with chiroptical properties and configurational stability typical for higher helicenes, while the radially conjugated seven para-phenylenes largely determine the optoelectronic properties. The structure of the helicene carbon nanoohop was unambiguously characterized by NMR, MS and X-ray analysis that revealed that it possesses a topology of a Möbius strip in the solid state and in solution. The chirality transfers from the [6]helicene to the para-phenylenes and leads to a pronounced circular dichroism and bright circularly polarized luminescence, which is affected by the structural topology of the nanohoop.

Keywords: Chirality; Circularly Polarized Luminescence; Cycloparaphenylenes; Helicenes; Molecular Nanocarbons; Möbius Topology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon
  • Luminescence*
  • Polycyclic Compounds* / chemistry
  • Stereoisomerism

Substances

  • Polycyclic Compounds
  • helicenes
  • Carbon