4H-dithieno[2,3-b:3',2'-e][1,4]thiazines--synthesis and electronic properties of a novel class of electron rich redox systems |
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Authors: | Dostert Catherine Wanstrath Claudia Frank Walter Müller Thomas J J |
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Institution: | Lehrstuhl für Organische Chemie, Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universit?t Düsseldorf, Universit?tsstra?e 1, D-40225, Düsseldorf, Germany. |
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Abstract: | Quantum chemical screening reveals that 4H-dithieno2,3-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-dithieno2,3-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. |
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