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Triply Bonded Pancake π-Dimers Stabilized by Tetravalent Actinides. | LitMetric

AI Article Synopsis

  • Aromatic π-stacking is a weak, noncovalent interaction that can complicate material design but can lead to stronger "pancake" bonds when involving unpaired electrons.
  • Researchers synthesized six-electron triple pancake bonds using the reduction of hexaazatrinaphthylene (HAN) and found a structure consisting of multicenter covalent bonds.
  • The study confirms these interactions through experimental absorption spectra and highlights the potential for new molecular conductors and spin-based materials.

Article Abstract

Aromatic π-stacking is a weakly attractive, noncovalent interaction often found in biological macromolecules and synthetic supramolecular chemistry. The weak nondirectional nature of π-stacking can present challenges in the design of materials owing to their weak, nondirectional nature. However, when aromatic π-systems contain an unpaired electron, stronger attraction involving face-to-face π-orbital overlap is possible, resulting in covalent so-called "pancake" bonds. Two-electron, multicenter single pancake bonds are well known, whereas four-electron double pancake bonds are rare. Higher-order pancake bonds have been predicted, but experimental systems are unknown. Here, we show that six-electron triple pancake bonds can be synthesized by a 3-fold reduction of hexaazatrinaphthylene (HAN) and subsequent stacking of the [HAN] triradicals. Our analysis reveals a multicenter covalent triple pancake bond consisting of a σ-orbital and two equivalent π-orbitals. An electrostatic stabilizing role is established for the tetravalent thorium and uranium ions in these systems. We also show that the electronic absorption spectrum of the triple pancake bonds closely matches computational predictions, providing experimental verification of these unique interactions. The discovery of conductivity in thin films of triply bonded π-dimers presents new opportunities for the discovery of single-component molecular conductors and other spin-based molecular materials.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10870716PMC
http://dx.doi.org/10.1021/jacs.3c13914DOI Listing

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