Jump to main content
Jump to site search

Issue 5, 2017
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 09 Mar 2017, accepted on 31 Mar 2017 and first published on 04 Apr 2017


Article type: Research Article
DOI: 10.1039/C7QO00188F
Citation: Org. Chem. Front., 2017,4, 839-846
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements