A negatively curved π-expanded pyracylene comprising a tropylium cation
We disclose π-expanded pyracylenes and their cationic species comprising 7-membered rings. The compounds were synthesized by stepwise oxidative cyclodehydrogenation to monitor the effect of successive cyclization on the structural and optoelectronic properties. As shown by X-ray crystallography, the...
Saved in:
| Main Authors: | , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
22 September 2023
|
| In: |
Angewandte Chemie. International edition
Year: 2023, Volume: 62, Issue: 46, Pages: 1-7 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.202312740 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/anie.202312740 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202312740 
|
| Author Notes: | Jan Borstelmann, John Bergner, Frank Rominger, and Milan Kivala |
| Summary: | We disclose π-expanded pyracylenes and their cationic species comprising 7-membered rings. The compounds were synthesized by stepwise oxidative cyclodehydrogenation to monitor the effect of successive cyclization on the structural and optoelectronic properties. As shown by X-ray crystallography, the complete cyclization leads to a boat-shaped scaffold featuring negative curvature provided by the 7-membered ring. The embedded tropone unit enabled the convenient generation of a stabilized tropylium cation, showing bathochromically shifted absorption bands reaching into the near-infrared region beyond 1000 nm. The altered structural features, supported by theoretical calculations, point towards the positively charged 7-membered ring having aromatic character. |
|---|---|
| Item Description: | Gesehen am 13.11.2023 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.202312740 |