Abstract
1,3,4,6-Tetraphenylpentalene (Ph 4Pn) has been synthesised by chemical oxidation of the corresponding pentalenide complex Mg[Ph 4Pn] with iodine. Ph 4Pn is a rare example of a room-temperature stable hydrocarbon that is antiaromatic by Hückel's rule and has been fully characterised by NMR and UV-vis spectroscopy, mass spectrometry as well as single-crystal X-ray diffraction. Quantum chemical studies including nucleus-independent chemical shift (NICS) and anisotropy of the induced current density (ACID) calculations showed the existence of an 8π antiaromatic core decorated with four independent 6π aromatic substituents. The formation of Ph 4Pn is reversible and it can be reduced back to the 10π aromatic Ph 4Pn 2- with potassium.
| Original language | English |
|---|---|
| Pages (from-to) | 952-961 |
| Journal | Chemical Science |
| Volume | 16 |
| Issue number | 2 |
| Early online date | 25 Nov 2024 |
| DOIs | |
| Publication status | Published - 14 Jan 2025 |
Data Availability Statement
Crystallographic datasets are available from the CCDC deposition number 2335451, and other analytical data can be found in the ESI.†Funding
UH and HJS thank the Royal Society (award UF160458) and the University of Bath for funding this work. HH and AH thank the German Research Foundation (DFG) for funding through the Heisenberg Grant HE 6171/9-1 (468457264). Kathryn Proctor (University of Bath) is acknowledged for assistance with conducting the mass spectrometry measurements, and we thank Simon Lewis and Dan Pantos (University of Bath) for stimulating discussions about aromaticity.
| Funders | Funder number |
|---|---|
| Royal Society | UF160458 |
| Deutsche Forschungsgemeinschaft | 468457264, HE 6171/9-1 |