Tetraazacoronenes and Their Dimers, Trimers and Tetramers Article Swipe

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Cyclobutene Chemistry Dimer Zirconium Cyclobutadiene Photochemistry Fluorescence Crystallography Absorption (acoustics) Molecule Materials science Inorganic chemistry Organic chemistry Ring (chemistry) Quantum mechanics Composite material Physics

Robert Eichelmann , Joachim Ballmann , Lutz H. Gade ·

YOU? · · 2023 · Open Access · · DOI: https://doi.org/10.1002/anie.202309198 · OA: W4383302270

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.