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...
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| Main Authors: | , , |
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| Format: | Article (Journal) Editorial |
| Language: | English |
| Published: |
July 15, 2025
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| In: |
Organic letters
Year: 2025, Volume: 27, Issue: 29, Pages: 7944-7949 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.5c02272 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.orglett.5c02272
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| Author Notes: | Simone F. Ebel, Frank Rominger, and Michael Mastalerz |
| Summary: | 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. |
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| Item Description: | Gesehen am 10.11.2025 |
| Physical Description: | Online Resource |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.5c02272 |