Methyl 4-(1,3a,6a-triazapentalen-3-yl)benzoate () 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 with various aryl halides resulted in 3,6-diaryltriazapentalenes , although mostly in poor yields. Bromination of followed by Suzuki coupling, on the other hand, requires a more delicate procedure, but gave arylated products with the same regiochemistry () in moderate to good yields. The structure of 6-phenyltriazapentalene 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.
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| http://dx.doi.org/10.3390/molecules29102229 | DOI Listing |
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