[4]Cyclofluorene: Unexpected Influence of Alkyl Chain Length

Lambert Sicard, Olivier Jeannin, Joëlle Rault-Berthelot, Cassandre Quinton, Cyril Poriel

Chempluschem. 2018 Sep;83(9):874-880.

PMID: 31950686

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AS26413	Propyl 4-hydroxybenzoate-ring-13C6 solution			Price