Design strategies and applications of novel functionalized phenazine derivatives: a review

Abstract

Phenazine derivatives have made significant achievement owing to favorable photophysical and chemical properties in recent years. Nevertheless, the overview about phenazine derivatives is few reported in optoelectronic area. Herein, we...

Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

“…The phenothiazines and the phenazines are exceptional and versatile classes of electron-rich nitrogen heterocycles with broad pharmaceutical profiles and rich materials sciences applications [ 1 , 2 , 3 ]. A seemingly small difference between these types of molecules, i.e., the presence of a six-membered ring with nitrogen and sulfur atoms for phenothiazines and two nitrogen atoms for phenazines, manifests itself profoundly through their physicochemical and structural properties.…”

Covalent Organic Frameworks: Cutting‐Edge Materials for Carbon Dioxide Capture and Water Harvesting from Air

“…[79][80][81] However, since one of the monomers is limited to 1,3,5-triformylphloroglucinol, [82] there is still scope to explore structural diversity such as imine linkages. Highly coveted for its planar fused architecture which can impart COFs with exceptional stability and redox properties, [83,84] phenazine linkage was introduced in COFs for the first time in 2023. [85] Favored with extended π-delocalization, CSÀ COF showed its efficiency when applied in solar cells.…”

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

“…Phenazines are tricyclic dibenzannulated heterocycles containing a central pyrazine core, well-known as naturally occurring substances, biologically active species, and dyestuffs (e.g., safranine, neutral red). − Beyond being popular chromophores, their unique optical and electrochemical properties allowed for their use as chemosensors , or photocatalysts for photopolymerization or cross-coupling reactions. − In organic electronics, phenazines have demonstrated their potential as low-bandgap semiconductors in solar cells , and as electroactive compounds in batteries. , They have also found a particular interest for the elaboration of organic light-emitting diodes (OLEDs), notably due to the rigidity and electron-withdrawing character of the phenazine core, which is beneficial for designing thermally activated delayed fluorescent dyes, as exemplified with the recent report of sterically hindered tetrabenzophenazine-phenoxazines that afforded efficient orange-red OLEDs . Furthermore, the straightforward synthesis of simple phenazines through polycondensation reactions enables the preparation of various π-extended planar chromophores derived from azaacenes, and this motif can be found in many polyaromatic heterocyclic nanographenes, two-dimensional conjugated macrocycles, 3D porous architectures, − as well as helicoidal derivatives. , …”

“…Interestingly, a handful of works report the formation of phenazines via the intermolecular formation of C–N bonds in the ortho position between two electron-rich aromatic amines . Such a reaction, particularly relevant for the present contribution, can occur in the presence of an oxidant such as dioxygen, potassium dioxide or 2,3-dichloro-5,6-dicyano- p -benzoquinone (DDQ) to form extended phenazines from amino derivatives of naphthalene, carbazole, or anthracene. − These protocols principally afford mono- to tetrasubstituted phenazines, the principal examples of per-substituted derivatives being the tetrabenzo­[ a , c , h , j ]­phenazines. , …”