Tetracyclopenta[def,jkl,pqr,vwx]tetraphenylene: A potential tetraradicaloid hydrocarbon

Shunpei Nobusue, Hirokazu Miyoshi, Akihiro Shimizu, Ichiro Hisaki, Kotaro Fukuda, Masayoshi Nakano, Yoshito Tobe*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

66 Scopus citations


A tetramesityl derivative of hitherto unknown tetracyclopenta[def,jkl,pqr,vwx]tetraphenylene (TCPTP), which is a potential tetraradicaloid hydrocarbon, was synthesized. Theoretical calculations based on spin-flip time-dependent density functional theory predict that the closed-shell D2h form of TCPTP is more stable than the open-shell D4h form with its slightly tetraradical character. The tetramesityl derivative (Mes)4-TCPTP exhibits remarkable antiaromaticity as a result of the peripheral 20-π-electron circuit, which causes an absorption maximum at a long wavelength and a small HOMO-LUMO gap. In solution, (Mes)4-TCPTP most likely adopts rapidly equilibrating D2h structures that interconvert via the D4h transition state. X-ray crystallographic analysis showed (Mes)4-TCPTP as an approximate D2h structure.

Original languageEnglish
Pages (from-to)2090-2094
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number7
StatePublished - 9 Feb 2015


  • Antiaromaticity
  • Corannulenes
  • Singlet diradical
  • Singlet tetraradical
  • Valence tautomerization

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