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5-Aryl-2,2′-bipyridines bearing fluorinated anilines residues at C6 position: synthesis and photophysical properties

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Abstract

A convenient synthetic approach to 5-aryl-2,2′-bipyridines bearing a (poly)fluorine-containing aniline residue at position C6 based on sequential ipso-substitution of the cyano group at position C5 of 3-(2-pyridyl)-1,2,4-triazines and the aza-Diels–Alder reaction has been proposed. The influence of the number and the position of the fluorine atoms on the reactivity of fluoroanilines has been estimated by means of DFT calculations. It was shown that the reaction cannot be realized if a nitro group is present in the ortho-position or two fluorine atoms occupied the ortho-positions in aniline. Photophysical properties of prospective “push–pull” fluorophores have been studied. Incorporation of fluorine atom into position 4 of aniline fragment in 5-p-tolylbipyridines causes small bathochromic shift of emission maximum, whereas the replacement of the methoxy group at the position C4 of the aniline moiety in 5-(4-methoxyphenyl)-2,2′-bipyridine with fluorine atom leads to a significant hypsochromic shift of emission maximum and to significant increase in quantum yield; the positive solvatochromism has been observed.

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Acknowledgements

This work was supported by the Russian Foundation for Basic Research (Grant 19-53-55002) and Russian Scientific Foundation (Grant 19-73-10144).

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Author notes

  1. Dmitry S. Kopchuk, Ekaterina S. Starnovskaya, Yaroslav K. Shtaitz, Albert F. Khasanov, Grigory A. Kim, Emiliya V. Nosova, Alexey P. Krinochkin, Grigory V. Zyryanov, Vladimir L. Rusinov & Oleg N. Chupakhin

    Present address: Department of Organic and Biomolecular Chemistry, Ural Federal University, 19 Mira St., Ekaterinburg, Russia, 620002

Authors and Affiliations

  1. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya St./20 Akademicheskaya St., Ekaterinburg, Russia, 620137

    Dmitry S. Kopchuk, Ekaterina S. Starnovskaya, Albert F. Khasanov, Grigory A. Kim, Emiliya V. Nosova, Alexey P. Krinochkin, Grigory V. Zyryanov, Vladimir L. Rusinov & Oleg N. Chupakhin

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  1. Dmitry S. Kopchuk
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  2. Ekaterina S. Starnovskaya
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Correspondence to Emiliya V. Nosova.

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Kopchuk, D.S., Starnovskaya, E.S., Shtaitz, Y.K. et al. 5-Aryl-2,2′-bipyridines bearing fluorinated anilines residues at C6 position: synthesis and photophysical properties. Res Chem Intermed 46, 3929–3944 (2020). https://doi.org/10.1007/s11164-020-04182-z

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