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PreprintCC BYChemRxiv

A Negatively Curved Porphyrin [10]Circulene

  • Sara Borghi1,2
  • Raymond M. van Rijn1,2
  • Ka Man Cheung1,2
  • Lene A. Gödde1,2
  • Harold W. Mackenzie1,2
  • Harry L. Anderson1,2
  1. 1Department of Chemistry
  2. 2University of Oxford
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Abstract

A curved five-porphyrin circulene has been synthesized through oxidative fusion of a cyclic precursor, prepared by Yamamoto coupling. The saddle-shaped geometry of this molecule was confirmed by single-crystal X-ray diffraction. In solution, it undergoes a rapid saddle-to-saddle inversion, even at 200 K, resulting in a simple 1 H NMR spectrum. Despite its pronounced negative curvature (Gauss curvature: –0.30 Å –2 ), it exhibits efficient electronic delocalization, with an electrochemical band gap of 0.88 eV and near-infrared absorption (λ max 1200 nm). It has a high affinity for C 60 and C 70 , in toluene at 298 K. There is no significant bond length alternation around the central 10-membered ring, and computational studies reveal a substantial diatropic current around this ring, establishing the porphyrin circulene as a globally aromatic curved nanographene.

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Cite

BibTeXRIS
BibTeX
@misc{borghi2026negatively,
  title = {{A Negatively Curved Porphyrin [10]Circulene}},
  author = {Sara Borghi and Raymond M. van Rijn and Ka Man Cheung and Lene A. Gödde and Harold W. Mackenzie and Harry L. Anderson},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15011177/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011177/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - A Negatively Curved Porphyrin [10]Circulene
AU  - Sara Borghi
AU  - Raymond M. van Rijn
AU  - Ka Man Cheung
AU  - Lene A. Gödde
AU  - Harold W. Mackenzie
AU  - Harry L. Anderson
PY  - 2026
DA  - 2026/10/28
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15011177/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011177/v1
AB  - A curved five-porphyrin circulene has been synthesized through oxidative fusion of a cyclic precursor, prepared by Yamamoto coupling. The saddle-shaped geometry of this molecule was confirmed by single-crystal X-ray diffraction. In solution, it undergoes a rapid saddle-to-saddle inversion, even at 200 K, resulting in a simple 1 H NMR spectrum. Despite its pronounced negative curvature (Gauss curvature: –0.30 Å –2 ), it exhibits efficient electronic delocalization, with an electrochemical band gap of 0.88 eV and near-infrared absorption (λ max 1200 nm). It has a high affinity for C 60 and C 70 , in toluene at 298 K. There is no significant bond length alternation around the central 10-membered ring, and computational studies reveal a substantial diatropic current around this ring, establishing the porphyrin circulene as a globally aromatic curved nanographene.
ER  -