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Enantiopure synthesis of [5]helicene based molecular lemniscates and their use in chiroptical materials

Author

Listed:
  • Leah E. M. White

    (University of Bath)

  • Tiberiu-M. Gianga

    (Diamond Light Source Ltd.)

  • Fabienne Pradaux-Caggiano

    (University of Bath)

  • Chiara Faverio

    (University of Bath)

  • Andrea Taddeucci

    (Diamond Light Source Ltd.
    University of Pisa)

  • Henry S. Rzepa

    (Imperial College London MSRH)

  • Christian Jonhannesen

    (University of Antwerp)

  • Lauren E. Hatcher

    (Cardiff University)

  • Giuliano Siligardi

    (Diamond Light Source Ltd.)

  • David R. Carbery

    (University of Bath)

  • G. Dan Pantoș

    (University of Bath)

Abstract

The ability to synthesise lemniscular molecules to allow for the study and application of their chiroptical properties is a notable technical challenge. Herein, we report the design and synthesis of enantiomers of a [5]helicenoid derived molecular lemniscate, in which two homochiral helicenes are linked via the formation of two azine motifs. We demonstrate that these molecules, and their helicenoid constituents, are also excellent chiral dopants that induce dissymmetry in the ground and excited states of the achiral emissive polymer F8BT, leading to high CPL activity. The ability to control the handedness of the helicenoid dopants via enantiopure synthesis affords control of the sign of CP emission. This manipulation of circularly polarised light is of great interest for optoelectronic technologies.

Suggested Citation

  • Leah E. M. White & Tiberiu-M. Gianga & Fabienne Pradaux-Caggiano & Chiara Faverio & Andrea Taddeucci & Henry S. Rzepa & Christian Jonhannesen & Lauren E. Hatcher & Giuliano Siligardi & David R. Carber, 2025. "Enantiopure synthesis of [5]helicene based molecular lemniscates and their use in chiroptical materials," Nature Communications, Nature, vol. 16(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-58162-1
    DOI: 10.1038/s41467-025-58162-1
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    References listed on IDEAS

    as
    1. Jessica Wade & James N. Hilfiker & Jochen R. Brandt & Letizia Liirò-Peluso & Li Wan & Xingyuan Shi & Francesco Salerno & Seán T. J. Ryan & Stefan Schöche & Oriol Arteaga & Tamás Jávorfi & Giuliano Sil, 2020. "Natural optical activity as the origin of the large chiroptical properties in π-conjugated polymer thin films," Nature Communications, Nature, vol. 11(1), pages 1-11, December.
    2. Inho Song & Jaeyong Ahn & Hyungju Ahn & Sang Hyuk Lee & Jianguo Mei & Nicholas A. Kotov & Joon Hak Oh, 2023. "Helical polymers for dissymmetric circularly polarized light imaging," Nature, Nature, vol. 617(7959), pages 92-99, May.
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