1,4-Thiazines and their Benzo Derivatives

Diethyl pyrrole-2,5-dicarboxylate

“…It seems likely that the reaction involves the loss of elemental sulfur, most likely from an anionic form of thiazine diester 6 as shown in Scheme 2. Although extrusion of sulfur from various ringfused thiazine systems to give the corresponding pyrroles is known to occur thermally [9][10][11], the corresponding reaction of monocyclic thiazines is rather rare [12], and the only similar examples we are aware of are a series of the isomeric 1,4-thiazine-2,6-diesters 7, which are reported to give the pyrrole diesters 8 upon treatment with triethylamine [13,14]. In light of the unexpected reaction involved in going from 6 to 1, we took the opportunity to confirm the product structure unambiguously through x-ray diffraction.…”

Radical cations and dications of bis[1]benzothieno[1,4]thiazine isomers

“…[15][16][17][18][19] They possess low oxidation potentials with fully chemically reversible oneelectron oxidations, low band gaps, and luminescent properties. [20][21][22] In addition to their convenient accessibility, their intrinsic properties are easily fine tunable by synthetic functionalization. 22,23 Furthermore, the remarkable stability of their radical cations is crucial for providing efficient charge transfer as hole conductors.…”

Dithienothiazine Copolymers – Synthesis and Electronic Properties of Novel Redox-Active Fluorescent Polymers

“…7 As donor components, ensuring high lying HOMO energies and generation of stable radical cations upon oxidation triarylamines 8 and thiophene motifs 9 have received significant prominence as hole transporters. Furthermore, S,N-containing tricycles, such as 3,7-disubstituted phenothiazines, exhibit fully reversible one-electron oxidations at low potentials, 10 extraordinarily stable radical cations, 11 and pronounced luminescence. For instance, OLEDs 12 as well as redox switchable luminophores 13 have been developed based on oligomeric and polymeric phenothiazines.…”