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Electron sharing and anion-π recognition in molecular triangular prisms.

Severin T Schneebeli1, Marco Frasconi, Zhichang Liu

  • 1Center for the Chemistry of Integrated Systems, Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA).

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|November 15, 2013
PubMed
Summary

Triangular molecular prisms with electron-rich naphthalenediimide centers encapsulate anions, forming supramolecular helices. Chirality from the prisms transfers to these single-handed helices in the solid state.

Keywords:
anion-π interactionshelical π-π stackingmacrocyclesmixed-valence compoundsradical anions

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Naphthalenediimide (NDI) derivatives are known for their electron-deficient properties and redox activity.
  • Molecular prisms offer unique architectures for host-guest chemistry and self-assembly.
  • Controlling chirality in self-assembled structures is a key challenge in supramolecular chemistry.

Purpose of the Study:

  • To investigate the self-assembly behavior of triangular molecular prisms with naphthalenediimide (NDI) redox centers.
  • To explore the encapsulation of linear anions within the electron-deficient cavities of these prisms.
  • To study the transfer of chirality from the molecular prisms to the resulting supramolecular assemblies.

Main Methods:

  • Synthesis of triangular molecular prisms featuring NDI units.
  • Crystallization studies to form solid-state supramolecular structures.
  • Spectroscopic and crystallographic analysis to characterize the assemblies and chirality.

Main Results:

  • Triangular molecular prisms successfully encapsulate linear triiodide anions within their electron-deficient cavities.
  • The encapsulation induces the formation of supramolecular helices in the solid state.
  • Chirality present in the six chiral centers of the molecular prisms is effectively transferred to the single-handed helices.

Conclusions:

  • Electron sharing within NDI redox centers of molecular prisms facilitates anion encapsulation.
  • Supramolecular helices with single-handed chirality can be formed through host-guest interactions.
  • This work demonstrates a strategy for chirality transfer in self-assembled systems.