Tetra(peri‐naphthylene)anthracene: A Near‐IR Fluorophore with Four‐Stage Amphoteric Redox Properties

• Published in: Chemistry : a European journal 2023-01, Vol.29 (6), p.e202203101-n/a
• Main Authors: Frisch, Sabine, Neiß, Christian, Lindenthal, Sebastian, Zorn, Nicolas F., Rominger, Frank, Görling, Andreas, Zaumseil, Jana, Kivala, Milan
• Format: Article
• Language: English
• Subjects: Anthracene; Chemical compounds; Chemistry; chromophores; cyclopentannulation; Fluorophores; near-IR fluorophores; polycycles; redox amphoteric compounds; Redox properties
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202203101

A novel, benign synthetic strategy towards soluble tetra(peri‐naphthylene)anthracene (TPNA) decorated with triisopropylsilylethynyl substituents has been established. The compound is perfectly stable under ambient conditions in air and features intense and strongly bathochromically shifted UV/vis absorption and emission bands reaching to near‐IR region beyond 900 nm. Cyclic voltammetry measurements revealed four facilitated reversible redox events comprising two oxidations and two reductions. These remarkable experimental findings were corroborated by theoretical studies to identify the TPNA platform a particularly useful candidate for the development of functional near‐IR fluorophores upon appropriate functionalization. Towards the red‐light area. A reliable synthesis of a new tetra(peri‐naphthylene)anthracene derivative decorated with triisopropylsilylethynyl moieties has been established. The soluble compound features strongly bathochromically shifted absorption and emission bands reaching into the near‐IR region and is prone to four facilitated redox steps. The experimental results, corroborated by theoretical studies, identified the π‐conjugated polycyclic scaffold as a particularly promising candidate for the development of redox‐active near‐IR fluorophores.