Fungus Pigments. XV. On the Synthesis of Benzobisbenzofuranquinones.

Gripenberg, Jarl; Lounasmaa, Mauri; Cederberg, G.; Jensen, R. B.; Pederson, C. Th; Larsen, Erik

doi:10.3891/acta.chem.scand.19-1063

Cited by 2 publications

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“…A small peak at δ 7.89 corresponds with the minor isomer. Integration of this isomer peak as well as the small isomer peaks detected in the C NMR support a >9:1 isomeric selectivity in favor of the [1,2‐b:5,4‐b′] substituted M1 with the other isomeric form expected to be the C2 symmetric [1,2‐b:4,5‐b′] form . Direct polymerization of M1 proved unsuccessful affording only low molecular weight oligomers.…”

Section: Resultsmentioning

confidence: 83%

“…To address this challenge, our attention was drawn to studies from over 50 years ago which examined the synthesis of pentacyclic benzodibenzofuranquinones (BDBFQ) through a one‐step condensation and ring closure reaction of chloranil with phenols (Fig. ) . While largely unstudied, these polycyclic units offer the possibility to rigidify the polymer backbone, reduce energetic disorder, and improve both the optical and electronic properties of the resulting materials .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of a versatile pentacyclic building block for organic electronics

McDearmon

Lim

O’Hara

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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A new pentacyclic building block, benzodibenzofuranquinone (BDBFQ), is synthesized in a single step from the inexpensive and readily available feedstocks chloranil and 3bromophenol. This versatile repeat unit is incorporated into a series of conjugated materials as either the redox active quinone form or as an electron-rich dialkylated benzodibenzofuran (BDBF) unit. To illustrate the performance that can be obtained from these systems, optical and electrochemical properties were studied via UV-vis-NIR spectroscopy and cyclic voltammetry. Thin-film morphology was characterized via grazing incidence wide-angle X-ray scattering with thin-film fieldeffect transistor measurements further demonstrating the utility of this system.

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Section: Resultsmentioning

confidence: 83%

Section: Introductionmentioning

confidence: 99%