1,2,3,4‐Tetrafluorobiphenylene: A Prototype Janus‐Headed Scaffold for Ambipolar Materials

Nikulshin, P.V.; Makarov, A.Y.; Koskin, I.P.; Becker, C.S.; Kazantsev, M.S.; Beckmann, J.; Balmohammadi, Y.; Grabowsky, S.; Mebs, S.; Naumova, O.V.; Protasov, D.Y.; Svit, K.A.; Irtegova, I.G.; Radiush, E.A.; Bagryanskaya, I.Y.; Shundrin, L.A.; Zibarev, A.V.

Авторы: Nikulshin Pavel V., Makarov Alexander Yu, Koskin Igor P., Becker Christina S., Kazantsev Maxim S., Beckmann Jens, Balmohammadi Yaser, Grabowsky Simon, Mebs Stefan, Naumova Olga V., Protasov Dmitry Yu, Svit Kirill A., Irtegova Irina G., Radiush Ekaterina A., Bagryanskaya Irina Yu, Shundrin Leonid A., Zibarev Andrey V.
Журнал: ChemPlusChem
Год издания: 2024
Издательство: WILEY-VCH
Местоположение издательства: INC, 605 THIRD AVE, NEW YORK, USA, NY, 10158-0012
DOI: 10.1002/cplu.202300692
Аннотация: The title compound was synthesized by Ullmann cross-coupling in low yield as the first representative of [n]phenylene containing hydrocarbon and fluorocarbon rings. Stille/Suzuki-Miyaura cross-coupling reactions, as well as substitution of fluorine in suitable starting compounds, failed to give the same product. The geometric and electronic structures of the title compound were studied by X-ray diffraction, cyclic voltammetry and density functional theory calculations, together with Hirshfeld surface and reduced density gradient analyses. The crystal structure features head-to-tail π-stacking and other fluorine-related secondary bonding interactions. From the nucleus-independent chemical shifts descriptor, the four-membered ring of the title compound is antiaromatic, and the six-membered rings are aromatic. The Janus molecule is highly polarized; and the six-membered fluoro- and hydrocarbon rings are Lewis π-acidic and π-basic, respectively. The electrochemically-generated radical cation of the title compound is long-lived as characterized by electron paramagnetic resonance, whereas the radical anion is unstable in solution. The title compound reveals electrical properties of an insulator. On expanding its molecular scaffold towards partially fluorinated [n]phenylenes (n≥2), the properties presumably can be transformed into those of semiconductors. In this context, the title compound is suggested as a prototype scaffold for ambipolar materials for organic electronics and spintronics.
Добавил в систему: Никульшин Павел Викторович

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1,2,3,4‐Tetrafluorobiphenylene: A Prototype Janus‐Headed Scaffold for Ambipolar Materialsстатья

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