Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.



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
Please wait while Download options loads

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, Advance Article
  •   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, Advance Article , DOI: 10.1039/C7QO00188F

Search articles by author