Tetraazacoronenes and their dimers, trimers and tetramers

• Verfasst von: Eichelmann, Robert [VerfasserIn]
• Verfasst von: Ballmann, Joachim [VerfasserIn]
• Verfasst von: Gade, Lutz H. [VerfasserIn]
• Titel: Tetraazacoronenes and their dimers, trimers and tetramers
• Titelzusatz: dedicated to Professor Andreas Grohmann on the occasion of his 60th birthday
• Gefeierte Person: Grohmann, Andreas [GefeierteR]
• Verf.angabe: Robert Eichelmann, Joachim Ballmann, and Lutz H. Gade
• E-Jahr: 2023
• Jahr: August 28, 2023
• Umfang: 7 S.
• Illustrationen: Illustrationen
• Fussnoten: Online veröffentlicht: 6. Juli 2023 ; Gesehen am 28.02.2024
• Titel Quelle: Enthalten in: Angewandte Chemie. International edition
• Ort Quelle: Weinheim : Wiley-VCH, 1998
• Band/Heft Quelle: 62(2023), 35, Artikel-ID e202309198, Seite 1-7
• ISSN Quelle: 1521-3773
• DOI: doi:10.1002/anie.202309198
• Datenträger: Online-Ressource
• Dokumenttyp: Festschrift
• Sprache: eng
• Bibliogr. Hinweis: Forschungsdaten: Eichelmann, Robert: Tetraazacoronenes and their dimers, trimers and tetramers [data]
• Sach-SW: Azacoronenes
• Sach-SW: Fluorescence
• Sach-SW: N-Heteropolycycles
• Sach-SW: Organic Dyes
• Sach-SW: Theoretical Calculations
• K10plus-PPN: 1882080831

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 η4-cyclobutadiene-zirconium(IV) complex was isolated as an intermediate to cyclobutene-annulated derivatives. Using bis(pinacolatoboryl)vinyltrimethylsilane as a C2 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.