A high ortho regioselectivity in nucleophilic aromatic substitution in low polar solvents is reported in the reaction of polyfluorinated azobenzenes with anilines. o-Anilino substituted derivatives could be easily transformed into non-symmetric phenazines by acid catalyzed electrocyclization. Phenazines are interesting compounds for their important properties as bioactive molecules. In addition, these fluorinated phenazines manifest interesting spectroscopic and electronic properties that make them candidates for n-type organic semiconductor. Furthermore, the prepared phenazines show reversible reduction with the LUMO and HOMO energy level controlled by the electronic nature of the substituent on the non-fluorinated ring of the system.

Vaghi, L., Coletta, M., Coghi, P., Andreosso, I., Beverina, L., Ruffo, R., et al. (2019). Fluorine substituted non-symmetric phenazines: A new synthetic protocol from polyfluorinated azobenzenes. ARKIVOC, 2019(5), 340-351 [10.24820/ark.5550190.p010.940].

Fluorine substituted non-symmetric phenazines: A new synthetic protocol from polyfluorinated azobenzenes

Vaghi, Luca
;
Coghi, Paolo;Andreosso, Ivan;Beverina, Luca;Ruffo, Riccardo;Papagni, Antonio
2019

Abstract

A high ortho regioselectivity in nucleophilic aromatic substitution in low polar solvents is reported in the reaction of polyfluorinated azobenzenes with anilines. o-Anilino substituted derivatives could be easily transformed into non-symmetric phenazines by acid catalyzed electrocyclization. Phenazines are interesting compounds for their important properties as bioactive molecules. In addition, these fluorinated phenazines manifest interesting spectroscopic and electronic properties that make them candidates for n-type organic semiconductor. Furthermore, the prepared phenazines show reversible reduction with the LUMO and HOMO energy level controlled by the electronic nature of the substituent on the non-fluorinated ring of the system.
Articolo in rivista - Articolo scientifico
Aromatic nucleophilic substitution; Azobenzenes; Nitrogen-containing heterocycles; Phenazines; Polyfluorinated compounds;
Polyfluorinated compounds, azobenzenes, phenazines, aromatic nucleophilic substitution, nitrogen-containing heterocycles
English
340
351
12
Vaghi, L., Coletta, M., Coghi, P., Andreosso, I., Beverina, L., Ruffo, R., et al. (2019). Fluorine substituted non-symmetric phenazines: A new synthetic protocol from polyfluorinated azobenzenes. ARKIVOC, 2019(5), 340-351 [10.24820/ark.5550190.p010.940].
Vaghi, L; Coletta, M; Coghi, P; Andreosso, I; Beverina, L; Ruffo, R; Papagni, A
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/241510
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