Issue 5, 2017

Radical cation and dication of a 4H-dithieno[2,3-b:3′,2′-e][1,4]-thiazine

Abstract

A p-tert-butylphenyl substituted 4H-dithieno[2,3-b:3′,2′-e][1,4]thiazine was synthesized by twofold Buchwald–Hartwig coupling. The electronic properties (UV/Vis, cyclic voltammetry and spectroelectrochemistry) and the DFT- and TD DFT-calculated electronic structure reveal that the parent system and the radical cation and dication oxidation products are highly polarizable π-systems with strong charge transfer contributions. The radical cation and the dication were prepared by oxidation with antimony(V) pentachloride, giving stable deeply colored salts. EPR spectroscopy of the radical cation furnishes hyperfine coupling constants with the nitrogen nucleus and the α-thienyl protons. The dication is EPR silent and was structurally characterized by recording an NMR spectrum.

Graphical abstract: Radical cation and dication of a 4H-dithieno[2,3-b:3′,2′-e][1,4]-thiazine

Supplementary files

Article information

Article type
Research Article
Submitted
09 Meur. 2017
Accepted
31 Meur. 2017
First published
04 Ebr. 2017

Org. Chem. Front., 2017,4, 839-846

Radical cation and dication of a 4H-dithieno[2,3-b:3′,2′-e][1,4]-thiazine

A. Schneeweis, A. Neidlinger, G. J. Reiss, W. Frank, K. Heinze and T. J. J. Müller, Org. Chem. Front., 2017, 4, 839 DOI: 10.1039/C7QO00188F

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