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Updated: Dec 30, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
[4]Cyclofluorene: Unexpected Influence of Alkyl Chain Length
Lambert Sicard1, Olivier Jeannin1, Joëlle Rault-Berthelot1
1University of Rennes, CNRS, ISCR-UMR 6226, F-35000, Rennes, France.
Abstract:
Presented here is the study of a new example of [4]cyclofluorene, with ethyl chains on the bridgeheads. Its molecular structure was established by solution NMR spectroscopy and single-crystal X-ray diffraction. Three successive oxidation processes and one reversible reduction were observed through cyclic voltammetry. The optical properties were characterized both in solution and thin film by UV/visible spectroscopy as well as stationary and time-resolved fluorescence. It was found that this [4]cyclofluorene displays different characteristics compared with the other [4]cyclofluorenes substituted by methyl or propyl chains: a simple modification of the chain length induces a non-negligible effect on the emission properties, which must be linked to the specific arrangement of the fluorene units. Furthermore, single-crystal X-ray diffraction reveals the formation of a pseudo-tubular solid-state arrangement of fully symmetrical ring structures, which was not observed for the other members of the [4]cyclofluorenes family. This finding could open the way to modulation of properties of cyclofluorenes through alkyl chain engineering.
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