Synthesis and Photophysical Properties of α-(N-Biphenyl)-Substituted 2,2'-Bipyridine-Based Push-Pull Fluorophores

Ekaterina S Starnovskaya; Dmitry S Kopchuk; Albert F Khasanov; Olga S Taniya; Igor L Nikonov; Maria I Valieva; Dmitry E Pavlyuk; Alexander S Novikov; Grigory V Zyryanov; Oleg N Chupakhin

doi:10.3390/molecules27206879

Synthesis and Photophysical Properties of α-(N-Biphenyl)-Substituted 2,2'-Bipyridine-Based Push-Pull Fluorophores

Molecules. 2022 Oct 13;27(20):6879. doi: 10.3390/molecules27206879.

Authors

Ekaterina S Starnovskaya^{1

2}, Dmitry S Kopchuk^{1

2}, Albert F Khasanov¹, Olga S Taniya¹, Igor L Nikonov^{1

2}, Maria I Valieva^{1

2}, Dmitry E Pavlyuk¹, Alexander S Novikov^{3

4}, Grigory V Zyryanov^{1

2}, Oleg N Chupakhin^{1

2}

Affiliations

¹ Chemical Engineering Institute, Ural Federal University, 19 Mira St., Yekaterinburg 620002, Russia.
² I. Ya. Postovsky Institute of Organic Synthesis of RAS, Ural Division, 22/20 S. Kovalevskoy/Akademicheskaya St., Yekaterinburg 62099, Russia.
³ Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg 199034, Russia.
⁴ Research Institute of Chemistry, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russia.

Abstract

A series of new α-(N-biphenyl)-substituted 2,2'-bipyridines were obtained through the combination of the ipso-nucleophilic aromatic substitution of the C5-cyano group, aza-Diels-Alder and Suzuki cross-coupling reactions, starting from 5-cyano-1,2,4-triazines. For the obtained compounds, photophysical and fluorosolvatochromic properties were studied. Fluorophores 3l and 3b demonstrated unexpected AIEE activity, while 3a and 3h showed promising nitroexplosive detection abilities.

Keywords: AIEE; Hammett constants; Lippert–Mataga equation; fluorescence; fluorosolvatochromic properties; nitroexplosive detection; α-(N-Biphenyl)-substituted 2,2′-bipyridines; “push–pull” fluorophores.

MeSH terms

2,2'-Dipyridyl*
Biphenyl Compounds
Fluorescent Dyes*
Ionophores
Triazines

Substances

diphenyl
2,2'-Dipyridyl
Fluorescent Dyes
Biphenyl Compounds
Ionophores
Triazines

Abstract

MeSH terms

Substances

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