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

Catherine Dostert; Claudia Wanstrath; Walter Frank; Thomas J.J. Müller

doi:10.1039/c2cc32731g

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

Catherine Dostert, Claudia Wanstrath, Walter Frank, Thomas J.J. Müller^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Research › peer-review

23 Citations (Scopus)

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.

Original language	English
Pages (from-to)	7271-7273
Number of pages	3
Journal	Chemical Communications
Volume	48
Issue number	58
DOIs	https://doi.org/10.1039/c2cc32731g
Publication status	Published - 25 Jun 2012
Externally published	Yes

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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.",

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AU - Wanstrath, Claudia

AU - Frank, Walter

AU - Müller, Thomas J.J.

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N2 - 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.

AB - 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.

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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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