Tetraazacoronenes and Their Dimers, Trimers and Tetramers

Abstract

Abstract Tetraazacoronenes were synthesized from bay ‐functionalized tetraazaperylenes by Zr‐mediated cyclization and four‐fold Suzuki–Miyaura cross coupling. In the Zr‐mediated approach, an η 4 ‐cyclobutadiene‐zirconium(IV) complex was isolated as an intermediate to cyclobutene‐annulated derivatives. Using bis(pinacolatoboryl)vinyltrimethylsilane as a C 2 building block gave the tetraazacoronene target compound along with the condensed azacoronene dimer as well as higher oligomers. The series of extended azacoronenes show highly resolved UV/Vis absorption bands with increased extinction coefficients for the extended aromatic cores and fluorescence quantum yields of up to 80 % at 659 nm.

Topics & Concepts