Thioether-Substituted Hexa-peri-hexabenzocoronenes

Mörsel S, Kellner R, Hirsch A (2023)


Publication Type: Journal article

Publication year: 2023

Journal

Book Volume: 26

Article Number: e202300299

Journal Issue: 20

DOI: 10.1002/ejoc.202300299

Abstract

The synthesis of novel mono-, di-, tri-, tetra-, and hexafluorinated hexa-peri-hexabenzocoronenes (HBCs) and their conversion into their thioether-substituted analogs is reported. The substitution reaction with the corresponding thiolates was performed microwave-assisted to significantly reduce the reaction time. With increasing amount of fluorination or thioether-substituents, a decreasing extinction coefficient can be observed for the HBCs. Successive addition of thioether-moieties leads to a bathochromic shift of the absorption and emission bands, whereas the nature of the attached thioether does not affect the optoelectronical properties. To further tune the electronic environment of the HBC core, a successive oxidation to the corresponding sulfone as well as the formation of the sulfonium salts were performed. With that, the electron-donating thioethers were transformed into electron-withdrawing substituents, resulting in an inversed electron demand in the periphery of the core. The so obtained compounds showed decreased extinction coefficients and a broadening of the absorption and emission bands.

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How to cite

APA:

Mörsel, S., Kellner, R., & Hirsch, A. (2023). Thioether-Substituted Hexa-peri-hexabenzocoronenes. European Journal of Organic Chemistry, 26(20). https://doi.org/10.1002/ejoc.202300299

MLA:

Mörsel, Sven, René Kellner, and Andreas Hirsch. "Thioether-Substituted Hexa-peri-hexabenzocoronenes." European Journal of Organic Chemistry 26.20 (2023).

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