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

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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Publication Details

Journal
Nature Communications
Published
2025-03-22
DOI
https://doi.org/10.1038/s41467-025-58162-1
Citations
7
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
Field-Weighted Citation Impact
5.62
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article

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

Chiara Faverio, Christian Johannessen, Fabienne Pradaux, David R. Carbery et al.
7 citations
Nature Communications
Synthesis and Properties of Aromatic Compounds
5.62
article

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

Chiara Faverio, Christian Johannessen, Fabienne Pradaux, David R. Carbery, Giuliano Siligardi, G. Dan Pantoş, Lauren E. Hatcher, Henry S. Rzepa, Andrea Taddeucci, Tiberiu‐Marius Gianga, Leah White
article en
7 citations

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.

Nature CommunicationsVol. 16(1)
University of Pisa (IT), University of Antwerp (BE), Diamond Light Source (GB), Imperial College London (GB), University of Bath (GB), Cardiff University (GB), Bath Spa University (GB)
Openalex Percentile: Top 5%
Synthesis and Properties of Aromatic Compounds
5.62
DOIOpen Access PDFOpenAlex
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Enantiopure synthesis of [5]helicene based molecular lemniscates and their use in chiroptical materials — Chiara Faverio, Christian Johannessen, et al. · Nature Communications (2025) | TGRS Research Map | TGRS