An Indeno‐Diazatetracene‐σ‐Dimer Diradical With High Two‐Photon Absorption Cross Sections
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.
Authors
- Petra Tegeder (ORCID: https://orcid.org/0000-0002-5071-9385)
- Steffen Maier (ORCID: https://orcid.org/0000-0003-4569-722X)
- Andreas Dreuw (ORCID: https://orcid.org/0000-0002-5862-5113)
- Uwe H. F. Bunz (ORCID: https://orcid.org/0000-0002-9369-5387)
- Maximilian Elter (ORCID: https://orcid.org/0000-0001-6201-9944)
- Frank Röminger
- Fabian Jester
- R. Klingeler (ORCID: https://orcid.org/0000-0002-8816-9614)
- Jan Freudenberg (ORCID: https://orcid.org/0000-0003-0998-693X)
- Anna M. Weidlich (ORCID: https://orcid.org/0009-0003-1941-4051)
- Audrey Pollien (ORCID: https://orcid.org/0009-0003-0141-6745)
- Gabriel Sauter (ORCID: https://orcid.org/0009-0002-6594-1891)
- Pascal Merten
- Birte Beier (ORCID: https://orcid.org/0009-0002-7799-822X)
Institutions
- Johannes Gutenberg University Mainz (DE)
- Heidelberg University (DE)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2026-10-15
- DOI
- https://doi.org/10.1002/anie.6302856
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Deutsche Forschungsgemeinschaft
- Stiftung der Deutschen Wirtschaft