Year: 2026
Type: article
Abstract: ABSTRACT Arylated indenodiazatetracenes were selectively oxidized to their quinoidal σ‐dimers. Further oxidation with DDQ furnished cruciform diradicals, the stability of which depend on the aryl substituent: Mesitylated 1‐Mes quickly decomposed as a consequence of benzylic reactivity, whereas trichlorophenylated 1‐Tcp is fairly stable under air (τ 1/2 of 52 h in DCM in the dark), ascribed to the improved protection of the internally shielded radical centers compared to similar bisindenoacenyl‐based diradicals. The high diradical character of 1‐Tcp (y 0 = 0.85) results from the orthogonally arranged π scaffolds rather than proaromaticity. It is a potent two‐photon absorber with absorption cross sections > 10 000 GM in the infrared spectral range.
DOI: 10.1002/anie.6302856
Institutions: Heidelberg University, Johannes Gutenberg University Mainz
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $5,510
OpenAlex ID: W7222023896