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Synthesis and Functionalization of π-Extended [7]Carbohelicene.

Qing-Yue Song1, Zuping Xiong2, Guiyi Yang1

  • 1Guangdong Basic Research Center of Excellence for Aggregate Science, School of Science and Engineering, The Chinese University of Hong Kong (Shenzhen), Shenzhen, Guangdong, China.

Chemistry, an Asian Journal
|January 18, 2026
PubMed
Summary

We synthesized a new [7]helicene derivative, [7]-OTf, with reactive triflate groups. This versatile chiral molecule is suitable for creating advanced multifunctional materials.

Keywords:
chiralityfunctional materialshelicenenanographenepost modification

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Helicenes are unique chiral molecular scaffolds with promising applications in advanced materials.
  • Developing novel helicene derivatives with tunable properties is crucial for expanding their utility.

Purpose of the Study:

  • To report the efficient synthesis and characterization of a novel [7]helicene derivative, [7]-OTf.
  • To demonstrate the potential of [7]-OTf as a versatile platform for multifunctional chiral materials.

Main Methods:

  • Synthesis of the [7]helicene derivative [7]-OTf.
  • Characterization using X-ray crystallography.
  • Determination of racemization barrier and chiral separation via high-performance liquid chromatography.
  • Photophysical measurements (emission spectra, quantum yield).
  • Post-synthetic modification using Sonogashira coupling.

Main Results:

  • Efficient synthesis of [7]-OTf with reactive triflate groups was achieved.
  • X-ray crystallography confirmed the helical structure and enantiomer stacking.
  • A high racemization barrier (46.5 kcal·mol-1) allowed for chiral separation.
  • [7]-OTf displayed green emission (λem = 487 nm) with a 20% quantum yield and mirror-image chiroptical responses.
  • Successful post-synthetic modification via Sonogashira coupling demonstrated its versatility.

Conclusions:

  • [7]-OTf is a stable, enantiomerically separable chiral helicene derivative.
  • The compound exhibits promising photophysical properties for material applications.
  • [7]-OTf serves as a versatile platform for the development of advanced, modifiable chiral materials.