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Triple Pancake Bonding in Neutral π-Conjugated Dimers: a Computational Study.

Li-Juan Cui1, Miklos Kertesz2, Zhong-Hua Cui1,3

  • 1Institute of Atomic and Molecular Physics, Jilin University, Changchun 130023, China.

Journal of the American Chemical Society
|July 2, 2026
PubMed
Summary
This summary is machine-generated.

Researchers created a neutral molecule that forms a rare triple pancake bond through π-orbital overlap. This discovery offers new insights into high-order π-stacking interactions in molecules.

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Area of Science:

  • Materials Science
  • Quantum Chemistry
  • Supramolecular Chemistry

Background:

  • High-order pancake bonding is rare in π-conjugated molecules.
  • Previous studies on hexaazatrinaphthylene trianions ([HAN]3-) showed triple pancake bonds but were obscured by counterions.

Purpose of the Study:

  • To design a neutral hexaazatrinaphthylene derivative for studying intrinsic triple pancake bonding.
  • To investigate the nature and stability of intermolecular interactions in the neutral system.

Main Methods:

  • Designed a neutral HAN derivative, 1,5,9-trihydro-1,4,5,8,9,12-hexaazatriphenylene (HATH3).
  • Utilized computational methods to analyze the electronic structure and bonding in HATH3 dimers.
  • Calculated intermolecular separation and interaction energies for cofacial arrangements.

Main Results:

  • HATH3 exists in a quartet ground state with three singly occupied π-orbitals.
  • HATH3 monomers form stable dimers in trans- and cis-cofacial arrangements with ultrashort intermolecular distances (2.968 and 2.971 Å).
  • Triple pancake bonds are formed via three-electron sharing π-orbitals, with significant interaction energies (-158.6 and -135.1 kJ/mol).

Conclusions:

  • Neutral HATH3 dimers exhibit genuine triple pancake bonds, clarifying high-order π-stacking interactions.
  • Orbital interactions are the primary drivers of stability, supplemented by electrostatic and dispersion forces.
  • These findings are crucial for understanding aggregate and crystal formation driven by strong intermolecular forces.