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A Halogen-Bonded Dimeric Resorcinarene Capsule.

Ngong Kodiah Beyeh1, Fangfang Pan2, Kari Rissanen3

  • 1University of Jyvaskyla, Department of Chemistry, Nanoscience Center, P.O. Box. 35, 40014 University of Jyvaskyla (Finland). ngong.k.beyeh@jyu.fi.

Angewandte Chemie (International Ed. in English)
|May 8, 2015
PubMed
Summary
This summary is machine-generated.

Iodine (I2) forms a dimeric capsule with a resorcinarene molecule, creating a cavity that encapsulates guest molecules. This supramolecular structure is held together exclusively by halogen bonds.

Keywords:
halogen bondshydrogen bondsresorcinarenesself-assemblysupramolecular chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Crystal Engineering
  • Halogen Bonding

Background:

  • Macrocyclic molecules like resorcinarenes are known for their host-guest chemistry.
  • Halogen bonding is an important non-covalent interaction in molecular recognition.

Purpose of the Study:

  • To investigate the use of iodine as a bifunctional halogen-bond donor.
  • To construct a novel dimeric capsule using halogen bonds.
  • To explore the encapsulation capabilities of the formed capsule.

Main Methods:

  • Synthesis of N-cyclohexyl ammonium resorcinarene chloride (1).
  • Co-crystallization of resorcinarene 1 with iodine (I2) and 1,4-dioxane.
  • Structural characterization using X-ray diffraction.

Main Results:

  • Formation of a dimeric capsule [(1,4-dioxane)3@1(2)(I2)2] through halogen bonds between iodine and resorcinarene.
  • The capsule possesses a single cavity with a volume of 511 ų.
  • Successfully encapsulated three 1,4-dioxane guest molecules within the cavity.

Conclusions:

  • Iodine can effectively act as a bifunctional halogen-bond donor to assemble supramolecular capsules.
  • The resorcinarene-based dimeric capsule demonstrates efficient guest encapsulation.
  • This work highlights the potential of halogen bonding in designing functional supramolecular architectures.