Palladium-Catalyzed Arylations towards 3,6-Diaryl-1,3a,6a-triazapentalenes and Evaluation of Their Fluorescence Properties

Author:

Wang Yingchun1ORCID,Opsomer Tomas1ORCID,de Jong Flip2ORCID,Verhaeghe Davy2ORCID,Mulier Maarten1ORCID,Van Meervelt Luc3ORCID,Van der Auweraer Mark2,Dehaen Wim1ORCID

Affiliation:

1. Sustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

2. Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

3. Biochemistry, Molecular and Structural Biology, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

Abstract

Methyl 4-(1,3a,6a-triazapentalen-3-yl)benzoate (TAP1) shows interesting properties as a small molecule fluorophore. In the search for post-functionalization methods, palladium-catalyzed arylation reactions were demonstrated. Direct CH arylation reactions of TAP1 with various aryl halides resulted in 3,6-diaryltriazapentalenes TAP4, although mostly in poor yields. Bromination of TAP1 followed by Suzuki coupling, on the other hand, requires a more delicate procedure, but gave arylated products with the same regiochemistry (TAP4) in moderate to good yields. The structure of 6-phenyltriazapentalene TAP4a was confirmed by crystallographic analysis. In addition, the effect of the C6 arylation on the fluorescent properties of 3-aryl-1,3a,6a-triazapentalenes was studied in dichloromethane at room temperature and in 2-methyltetrahydrofuran at 77 K, while the photophysical properties of two saponified derivatives were measured in acetonitrile.

Funder

Research Council of KU Leuven

China Scholarship Council

Research Foundation—Flanders

Hercules Foundation of the Flemish Government

Hercules

Hercules Foundation

Publisher

MDPI AG

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