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Rigid tetranitroresorcinarenes.

Alexander Shivanyuk1, Adel Rafai Far, Julius Rebek

  • 1The Skaggs Institute for Chemical Biology and The Department of Chemistry, The Scripps Research Institute, MB-26, 10550 North Torrey Pines Rd., La Jolla, California 92037, USA.

Organic Letters
|April 27, 2002
PubMed
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Resorcinarene tetraesters undergo O-alkylation to form rigid octanitro resorcinarene. This compound serves as a promising scaffold for designing novel supramolecular structures.

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Resorcinarene derivatives are known for their potential in supramolecular chemistry.
  • Developing rigid molecular scaffolds is crucial for constructing ordered supramolecular architectures.

Purpose of the Study:

  • To synthesize a conformationally rigid resorcinarene derivative.
  • To explore the utility of this derivative as a scaffold for supramolecular structures.

Main Methods:

  • O-alkylation of C2v-symmetrical resorcinarene tetraesters.
  • Reaction with 1,3-difluoro-4,6-dinitrobenzene.

Main Results:

  • Successful synthesis of octanitro resorcinarene.
  • The resulting octanitro resorcinarene exhibits conformational rigidity.

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Conclusions:

  • Octanitro resorcinarene is readily accessible through O-alkylation.
  • This rigid resorcinarene scaffold holds potential for supramolecular design.