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1,4-Bis(p-tolylethynyl)benzene.

Alexander S Filatov1, Marina A Petrukhina

  • 1Department of Chemistry, University at Albany, SUNY, Albany, NY 12222, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|March 8, 2005
PubMed
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This study reveals a rod-like hydrocarbon molecule (C24H18) with planar benzene rings. These molecules self-assemble into stair-like networks through specific C-H...pi interactions, forming four hydrogen bonds each.

Area of Science:

  • Crystal engineering
  • Supramolecular chemistry
  • Organic solid-state chemistry

Background:

  • Understanding molecular packing is crucial for designing materials with specific properties.
  • Hydrocarbons offer a versatile platform for exploring non-covalent interactions in the solid state.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of the title hydrocarbon (C24H18).
  • To investigate the self-assembly behavior of C24H18 in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
  • Analysis of intermolecular interactions, including C-H...pi(arene) hydrogen bonds, was performed.

Main Results:

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  • The C24H18 molecule adopts a centrosymmetric, rod-like conformation with planar benzene rings.
  • Molecules aggregate into stacks along the [010] direction, forming a stair-like pseudo-two-dimensional network.
  • Each molecule participates in four hydrogen bonds, acting as both a C-H donor and a pi-arene acceptor.

Conclusions:

  • The observed C-H...pi(arene) interactions are key drivers for the self-assembly of C24H18 into extended networks.
  • The study provides insights into the formation of supramolecular architectures in hydrocarbon-based crystalline materials.