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

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 (S_N ^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

Publikationsverlauf

Eingereicht: 25. März 2021

Angenommen nach Revision: 05. Mai 2021

Accepted Manuscript online:
05. Mai 2021

Artikel online veröffentlicht:
10. Juni 2021

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