Embedding a planar antiaromatic cyclooctatetraene into a truxene-derived polycyclic aromatic hydrocarbon
Two contorted, monkey saddle-shaped polycyclic aromatic hydrocarbons (PAHs) with tailored substitution patterns were synthesized to enhance their inversion barriers. Along the way, a chiral, truxene-based PAH featuring a planar cyclooctatetraene (COT) core was discovered and structurally confirmed b...
Gespeichert in:
| Hauptverfasser: | , , |
|---|---|
| Dokumenttyp: | Article (Journal) Editorial |
| Sprache: | Englisch |
| Veröffentlicht: |
July 15, 2025
|
| In: |
Organic letters
Year: 2025, Jahrgang: 27, Heft: 29, Pages: 7944-7949 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.5c02272 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.orglett.5c02272
|
| Verfasserangaben: | Simone F. Ebel, Frank Rominger, and Michael Mastalerz |
| Zusammenfassung: | Two contorted, monkey saddle-shaped polycyclic aromatic hydrocarbons (PAHs) with tailored substitution patterns were synthesized to enhance their inversion barriers. Along the way, a chiral, truxene-based PAH featuring a planar cyclooctatetraene (COT) core was discovered and structurally confirmed by X-ray crystallography. Its antiaromatic character and optoelectronic properties were investigated and compared to those of its negatively curved precursor. Deuterium-labeling experiments and DFT calculations provided insights into the formation of the planar COT ring. |
|---|---|
| Beschreibung: | Gesehen am 10.11.2025 |
| Beschreibung: | Online Resource |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.5c02272 |