Multi-redox Indenofluorene Chromophores Incorporating Dithiafulvene Donor and Ene/Enediyne Acceptor Units

Submitting author affiliation:
University of Copenhagen, Copenhagen, Denmark

Beilstein Arch. 2023, 202343.

Published 16 Oct 2023

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Large donor-acceptor scaffolds derived from polycyclic aromatic hydrocarbons (PAHs) with tunable HOMO and LUMO energies are important for several applications, such as organic photovoltaics. Here we present a large selection of PAHs based on central indenofluorene (IF) or fluorene cores and containing various dithiafulvene (DTF) donor units that gain aromaticity upon oxidation, in some cases expanded by pyrrolo annelation, and a variety of acceptor units, such as vinylic diesters, enediynes, and cross-conjugated radiaannulenes (RAs) that gain aromaticity upon reduction. The optical and redox properties of these carbon-rich compounds were studied by UV-Vis absorption spectroscopy and cyclic voltammetry. Synthetically, the work explores IF diones or fluorenone as central building blocks by subjecting the carbonyl groups to a variety of reactions; that is, phosphite- or Lawesson’s reagent mediated olefination reactions (to introduce DTF motifs), Corey-Fuchs dibromoolefinations followed by Sonogashira couplings (to introduce enediynes motifs), and Knoevenagel condensations (to introduce vinylic diester motif). By a subsequent Glaser-Hay coupling reaction, a RA acceptor unit was introduced to provide an IF-DTF-RA donor-acceptor scaffold with a low-energy charge-transfer absorption and multi-redox behavior.

Keywords: Acetylenic scaffolds; Aromaticity; Polycyclic aromatic hydrocarbons; Redox properties; Tetrathiafulvalene

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Schøttler, C.; Lund-Rasmussen, K.; Broløs, L.; Vinterberg, P.; Bazikova, E.; Pedersen, V. B. R.; Nielsen, M. B. Beilstein Arch. 2023, 202343. doi:10.3762/bxiv.2023.43.v1

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