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Pancake Bonding: An Unusual Pi-Stacking Interaction.

Miklos Kertesz1

  • 1Chemistry Department and Institute of Soft Matter, Georgetown University, 37th and O Streets, NW, Washington, DC, 20057-1227, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 5, 2018
PubMed
Summary

Pancake bonding, a unique π-stacking interaction in radicals, features short distances and covalent-like electron sharing. This interaction is crucial for conducting organic materials.

Keywords:
conducting organic materialsdiradicalsextremely short intermolecular contactsgraphite compoundspi-stackingradicals

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Physical Chemistry

Background:

  • Atypical intermolecular interactions, termed pancake bonding, involve radicals with delocalized π-electrons.
  • These interactions exhibit shorter contact distances than typical van der Waals forces.

Purpose of the Study:

  • To survey the characteristics of pancake bonding.
  • To review experimental and computational aspects of pancake bonding.

Main Methods:

  • Review of experimental data on pancake bonded systems.
  • Analysis of computational studies on pancake bonding.

Main Results:

  • Pancake bonding occurs between radicals with delocalized π-electrons in singly occupied molecular orbitals (SOMOs).
  • Stabilization arises from SOMO orbital overlap, leading to direct atom-to-atom contact and specific orientations.
  • These interactions possess covalent-like electron sharing characteristics.
  • Pancake bonded dimers exhibit low-lying singlet and triplet states and distinct interlayer vibrational modes.
  • Van der Waals interactions are significantly modulated by Pauli repulsions in pancake bonded systems.
  • Fluxionality between π- and σ-bonded aggregates is observed.

Conclusions:

  • Pancake bonding is a significant interaction in functional organic materials.
  • Understanding pancake bonding is key to designing novel conducting and functional materials.