Tetrazo[1, 2‐b]indazoles: Straightforward Access to Nitrogen‐Rich Polyaromatics from s‐Tetrazines. (15th February 2023)

• Record Type: Journal Article
• Authors: Daher, Ahmad; Bousfiha, Asmae; Tolbatov, Iogann; Mboyi, Clève D.; Cattey, Hélène; Roisnel, Thierry; Fleurat‐Lessard, Paul; Hissler, Muriel; Hierso, Jean‐Cyrille; Bouit, Pierre‐Antoine; Roger, Julien
• Is Part Of: Angewandte Chemie. Volume 135:Number 13(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-02-15
• Subjects: Chromophores -- Palladium -- Redox Properties -- Tetrazines -- Tetrazo[1, 2-b]Indazoles; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202300571
• Languages: English
• ISSNs: 0044-8249

Abstract

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. Abstract : The straightforward access to a new class of aza‐polyaromatics is reported starting from fluorinated s ‐tetrazine. 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.