Zipping up tetraazaperylene: synthesis of tetraazacoronenes via double coupling in the bay positions

Abstract

Substituted tetraazacoronene fluorophores have been obtained selectively by double Suzuki–Miyaura cross coupling of symmetrically substituted 1,2-bis(pinacolatoboryl)alkenes with a bay-substituted octaazaperopyrenedioxide (OAPPDO). Subsequent Scholl reaction of the dimethoxyphenylated derivative allowed further π-extension of the azaperylene core, yielding a highly redox-active bis(phenanthro)tetraazacoronene.