Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 14, Pages 3582-3590Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201805085
Keywords
absorption; antiaromaticity; C-N cross-coupling; density functional calculations; polymorphism
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Funding
- Fonds der Chemischen Industrie
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Twofold Buchwald-Hartwig aminations selectively furnish three regioisomers of bis[1]benzothieno[1,4]thiazines; X-ray structure analyses and DFT calculations were corroborated for correlation of their electronic properties. All regioisomers outscore the parent compound phenothiazine with respect to a low-lying oxidation potential and reversible redox activity. The anti-anti bis[1]benzothieno[3,2-b:2 ',3 '-e][1,4]thiazines possess the lowest oxidation potentials in this series and displayed pronounced green luminescence in solution (phi(F)approximate to 20 %) and in the solid state. Syn-anti regioisomers were only weakly luminescent in solution, but showed aggregation-induced emission enhancement and solid-state luminescence. Most interestingly, X-ray structure analyses revealed that anti-anti derivatives have an amazingly coplanar structure of the pentacyclic anellated 1,4-thiazine system, emphasizing a structural similarity to heteroacenes. The calculated theoretical nucleus-independent chemical shifts additionally suggested that these 8 pi-electron core systems can be considered as the first electronically unbiased anellated 1,4-thiazines with antiaromatic character.
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