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RESEARCH PRODUCT
Radical cation and dication of a 4H-dithieno[2,3-b:3′,2′-e][1,4]-thiazine
Katja HeinzeGuido J. ReissWalter FrankAndreas NeidlingerThomas MüllerArno P. W. Schneeweissubject
010405 organic chemistryChemistryOrganic Chemistrychemistry.chemical_elementElectronic structureNuclear magnetic resonance spectroscopy010402 general chemistryPhotochemistry01 natural sciences0104 chemical scienceslaw.inventionDicationchemistry.chemical_compoundRadical ionAntimonyThiazinelawCyclic voltammetryElectron paramagnetic resonancedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-01-01 | Organic Chemistry Frontiers |