Controlling the helicity of π-conjugated oligomers by tuning the aromatic backbone twist

Anjan Bedi, Amit Manor Armon, Yael Diskin-Posner, Benny Bogosalvsky and Ori Gidron ()
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Anjan Bedi: The Hebrew University of Jerusalem
Amit Manor Armon: The Hebrew University of Jerusalem
Yael Diskin-Posner: Weizmann Institute of Science
Benny Bogosalvsky: The Hebrew University of Jerusalem
Ori Gidron: The Hebrew University of Jerusalem

Nature Communications, 2022, vol. 13, issue 1, 1-7

Abstract: Abstract The properties of π-conjugated oligomers and polymers are commonly controlled by side group engineering, main chain engineering, or conformational engineering. The last approach is typically limited to controlling the dihedral angle around the interring single bonds to prevent loss of π-conjugation. Here we propose a different approach to conformational engineering that involves controlling the twist of the aromatic units comprising the backbone by using a tether of varying lengths. We demonstrate this approach by synthesizing an inherently twisted building unit comprised of helically locked tethered acenes, bearing acetylene end-groups to enable backbone extension, which was applied in a series of nine helical oligomers with varying backbone length and twist. We find that the optical and electronic properties of π-conjugated systems may be determined by the additive, antagonistic, or independent effects of backbone length and twist angle. The twisted oligomers display chiral amplification, arising from the formation of secondary helical structures.

Date: 2022
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DOI: 10.1038/s41467-022-28072-7

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