Tetrazo[1,2‐B]indazoles: Straightforward Access to Nitrogen‐Rich Polyaromatics from s‐Tetrazines - Institut de Chimie Moléculaire de l'Université de Bourgogne Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie International Edition Année : 2023

Tetrazo[1,2‐B]indazoles: Straightforward Access to Nitrogen‐Rich Polyaromatics from s‐Tetrazines

Résumé

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.

Domaines

Chimie organique
Fichier principal
Vignette du fichier
Angew Chem Int Ed - 2023 - Daher - Tetrazo 1 2‐b indazoles Straightforward Access to Nitrogen‐Rich Polyaromatics from.pdf (3.57 Mo) Télécharger le fichier
Origine : Publication financée par une institution
licence : CC BY NC - Paternité - Pas d'utilisation commerciale

Dates et versions

hal-03962173 , version 1 (28-02-2023)

Identifiants

Citer

Ahmad Daher, Asmae Bousfiha, Iogann Tolbatov, Clève Dionel Mboyi, Hélène Cattey, et al.. Tetrazo[1,2‐B]indazoles: Straightforward Access to Nitrogen‐Rich Polyaromatics from s‐Tetrazines. Angewandte Chemie International Edition, 2023, 62, pp.e202300571. ⟨10.1002/anie.202300571⟩. ⟨hal-03962173⟩
64 Consultations
25 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More