A Strategy to Design Substituted Tetraamino-Phenazine Dyes and Access to an NIR-Absorbing Benzoquinonediimine-Fused Quinoxaline

Tatiana Munteanu (1) , Valérie Mazan (2) , Mourad Elhabiri (2) , Camil Benbouziyane (1) , Gabriel Canard (1) , Denis Jacquemin (3) , Olivier Siri (1) , Simon Pascal (1)

1 CINaM - Centre Interdisciplinaire de Nanoscience de Marseille
2 ECPM - École Européene de Chimie, Polymères et Matériaux de Strasbourg
3 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation

The straightforward access to N- or C-substituted dinitro-tetraamino-phenazines (P1–P5) is enabled in oxidative conditions via formation of two intermolecular C–N bonds from accessible 5-nitrobenzene-1,2,4-triamine precursors. The photophysical studies revealed green absorbing and orange-red emitting dyes, with enhanced fluorescence in the solid state. Further reduction of the nitro functions led to the isolation of a benzoquinonediimine-fused quinoxaline (P6), which undergoes diprotonation to form a dicationic coupled trimethine dye absorbing beyond 800 nm.

Mots clés: Dye; Phenazine; Near-infrared; Chromophore

Domaines: Chimie organique; Chimie théorique et/ou physique

Tatiana Munteanu, Valérie Mazan, Mourad Elhabiri, Camil Benbouziyane, Gabriel Canard, et al.. A Strategy to Design Substituted Tetraamino-Phenazine Dyes and Access to an NIR-Absorbing Benzoquinonediimine-Fused Quinoxaline. Organic Letters, In press, ⟨10.1021/acs.orglett.3c01251⟩. ⟨hal-04103261⟩