A new series of rod-like conjugated molecules with a pyrazine or a bipyrazine core. Synthesis and light emitting properties

Nordine Hebbar (1) , Catherine Fiol-Petit (1) , Yvan Ramondenc (1) , Gérard Plé (1) , Nelly Plé (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

In this paper, we describe the synthesis of a wide range of new rod-like conjugated molecules with a pyrazine or a bipyrazine core connected to electron acceptor (A) or donor (D) groups through π-conjugated bridges as transmitters for the internal charge transfer (ICT). The key steps of the synthesis involve metallation and subsequent transmetallation of 2-chloropyrazine derivatives followed by Sonogashira or Negishi cross-coupling reactions. The bipyrazine core was obtained with a Stille cross-coupling reaction between the 2-chloro-6-tributylstannylpyrazine and the 2-chloro-6-iodopyrazine. Functionalization of the 6,6′-dichloro-2,2′-bipyrazine was performed by metallation, transmetallation and cross-coupling reactions. The light emitting properties of the so obtained molecules are then investigated in terms of absorption and emission spectra.

Domaines: Chimie organique

Nordine Hebbar, Catherine Fiol-Petit, Yvan Ramondenc, Gérard Plé, Nelly Plé. A new series of rod-like conjugated molecules with a pyrazine or a bipyrazine core. Synthesis and light emitting properties. Tetrahedron, 2011, 67 (12), pp.2287-2298. ⟨10.1016/j.tet.2011.01.068⟩. ⟨hal-01018101⟩