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Synthesis 2021; 53(19): 3597-3607
DOI: 10.1055/a-1500-1343
paper

Novel Pentafluorophenyl- and Alkoxyphenyl-Appended 2,2′-Bipyridine Push–Pull Fluorophores: A Convenient Synthesis and Photophysical Studies

Timofey D. Moseev 
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
,
Egor A. Nikiforov
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
,
Mikhail V. Varaksin  ∗
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
,
Ekaterina S. Starnovskaya
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
,
Maria I. Savchuk
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
,
Igor L. Nikonov
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
,
Dmitry S. Kopchuk
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
,
Grigory V. Zyryanov
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
,
Oleg N. Chupakhin  ∗
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
,
Valery N. Charushin
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
› Author AffiliationsThe research was financially supported by the Russian Science Foundation (Project no. 20-73-10077).
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Abstract

A convenient method for the synthesis of new highly in non-polar solvents soluble photoactive pentafluorophenyl-substituted and extended alkoxyphenyl-substituted 2,2′-bipyridines is reported. The synthetic strategy for the preparation of such ligands involves a sequence of several structural transformations, such as O-alkylation, nucleophilic substitution of hydrogen (SN H) in 1,2,4-triazine precursors via the ‘addition–elimination’ scheme, and the subsequent conversion of the obtained 1,2,4-triazines into 2,2′-bipyridines by means of the aza-Diels–Alder reaction. The photophysical properties of the synthesized novel pentafluoroaryl-substituted 2,2′-bipyridines were comprehensively studied. The obtained photophysical data indicate the competitive advantages of the herein reported pentafluoroarylated push–pull fluorophores, bearing extended aliphatic moieties, over their analogues containing benzoxy or phenolic fragments in terms of improvement in quantum yield and well-pronounced positive solvatochromism confirmed by the mathematical analysis according to the Lippert–Mataga equation.

Key words

2,2′-bipyridines - 1,2,4-triazines - polyfluoroarenes - nucleophilic substitution of hydrogen - aza-Diels–Alder reaction - push–pull fluorophores - positive solvatochromism

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1500-1343.
  • Supporting Information


Publication History

Received: 25 March 2021

Accepted after revision: 05 May 2021

Accepted Manuscript online:
05 May 2021

Article published online:
10 June 2021

© 2021. Thieme. All rights reserved

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