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 Mär 2017
Accepted
31 Mär 2017
First published
04 Apr 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements