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

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. Carbery; G. Dan Pantoș

doi:10.1038/s41467-025-58162-1

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

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. Carbery, G. Dan Pantoș

Research output: Contribution to journal › Article › peer-review

6 Citations (SciVal)

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.

Original language	English
Article number	2837
Journal	Nature Communications
Volume	16
Issue number	1
Early online date	22 Mar 2025
DOIs	https://doi.org/10.1038/s41467-025-58162-1
Publication status	Published - 1 Dec 2025

Data Availability Statement

The data that support the findings of this study are available in the paper and its Supplementary Information. The experimental and computational datasets generated during this study are available at Imperial College Research Data Repository (https://doi.org/10.14469/hpc/3901)43. CCDC 2328087 (6) contains the supplementary crystallographic data for this paper. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. All data are available from the corresponding author upon request.

Funding

We thank the Engineering and Physical Sciences Research Council (EPSRC) DTA for L.E.M.W, EPSRC Programme Grant (EP/K004956/1), University of Bath Major Equipment Fund (VB-FS1RCU) and Diamond Light Source for the beam time and instruments access to B23 beamline (CM33876-1).

Funders	Funder number
Engineering and Physical Sciences Research Council	EP/K004956/1

ASJC Scopus subject areas

General Chemistry
General Biochemistry,Genetics and Molecular Biology
General Physics and Astronomy

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10.1038/s41467-025-58162-1Licence: CC BY

Cite this

White, L. E. M., Gianga, T. M., Pradaux-Caggiano, F., Faverio, C., Taddeucci, A., Rzepa, H. S., Jonhannesen, C., Hatcher, L. E., Siligardi, G., Carbery, D. R., & Pantoș, G. D. (2025). Enantiopure synthesis of [5]helicene based molecular lemniscates and their use in chiroptical materials. Nature Communications, 16(1), Article 2837. https://doi.org/10.1038/s41467-025-58162-1

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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.",

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AU - Faverio, Chiara

AU - Taddeucci, Andrea

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AB - 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.

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

Abstract

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Applying Long-Lived Metastable States in Switchable Functionality via Kinetic Control of Molecular Assembly

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

Abstract

Data Availability Statement

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

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Applying Long-Lived Metastable States in Switchable Functionality via Kinetic Control of Molecular Assembly

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