A Strategy to Design Substituted Tetraamino-Phenazine Dyes and Access to an NIR-Absorbing Benzoquinonediimine-Fused Quinoxaline - Archive ouverte HAL Access content directly
Journal Articles Organic Letters Year : 2023

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

Abstract

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.
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Dates and versions

hal-04103261 , version 1 (23-05-2023)

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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⟩
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