In:
Angewandte Chemie, Wiley, Vol. 135, No. 13 ( 2023-03-20)
Abstract:
The straightforward access to a new class of aza‐polyaromatics is reported. Starting from readily available fluorinated s‐tetrazine, a cyclization process with azide leads to the formation of an unprecedented tetrazo[1,2‐ b ]indazole or a bis‐tetrazo[1,2‐ b ]indazole ( cis and trans conformers). Based on the new nitrogen core, further N‐directed palladium‐catalyzed ortho ‐C−H bond functionalization allows the introduction of halides or acetates. The physicochemical properties of these compounds were studied by a joint experimental/theoretical approach. The tetrazo[1,2‐ b ]indazoles display solid‐state π‐stacking, low reduction potential, absorption in the visible range up to the near‐infrared, and intense fluorescence, depending on the molecular structure.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v135.13
DOI:
10.1002/ange.202300571
Language:
English
Publisher:
Wiley
Publication Date:
2023
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