4H-Dithieno[2,3-b:3′,2′-e][1,4]thiazines – synthesis and electronic properties of a novel class of electron rich redox systems

Abstract

Quantum chemical screening reveals that 4H-dithieno[2,3-b:3′,2′-e][1,4]thiazines possess the highest HOMO among four constitutional isomers, even 0.27 eV higher in energy than the well established 10H-phenothiazine. N-Substituted 4H-dithieno[2,3-b:3′,2′-e][1,4]thiazines are readily accessible by twofold Pd-catalyzed amination. According to cyclic voltammetry dithienothiazines are reversibly oxidized and can be considered as new donors for functional π-systems.