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"Rim-Differentiated" Pillar[6]arenes.

Yang Chao1,2, Tushar Ulhas Thikekar2, Wangjian Fang1

  • 1Institute for Molecular Design and Synthesis, School of Pharmaceutical Science & Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin, 300072, P. R. China.

Angewandte Chemie (International Ed. in English)
|April 22, 2022
PubMed
Summary

Researchers synthesized a novel rim-differentiated pillar[6]arene (RD-P[6]) using a silver trifluoroacetate template. This macrocycle exhibits conformational changes upon guest inclusion and can form adducts with C60, opening avenues for advanced materials.

Keywords:
Co-CrystalsHost-Guest ChemistryMacrocyclesPillar[n]arenesTiara[n]arenes

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Pillar[6]arenes are macrocyclic compounds with high symmetry.
  • Achieving regioselective synthesis of functionalized pillararenes remains a challenge.
  • Desymmetrization of macrocycles is key for creating complex molecular architectures.

Purpose of the Study:

  • To develop a direct and regioselective synthesis of a rim-differentiated pillar[6]arene (RD-P[6]).
  • To investigate the conformational behavior of RD-P[6] upon guest inclusion.
  • To explore the host-guest chemistry and adduct formation capabilities of RD-P[6].

Main Methods:

  • Direct synthesis of pillar[6]arene using a dimeric silver trifluoroacetate template.
  • Regioselective control among eight constitutional isomers.
  • Solid-state characterization of macrocycle conformation and guest inclusion effects.
  • Co-crystallization studies with C60 to form pillar[6]arene-C60 adducts.

Main Results:

  • Successful synthesis of a rim-differentiated pillar[6]arene (RD-P[6]) with high regioselectivity.
  • Observed switching of solid-state conformation from 1,3,5-alternate to rim-differentiated upon guest inclusion.
  • Demonstrated hosting of metal-containing molecules within the macrocycle cavity.
  • Formation of a pillar[6]arene-C60 adduct via co-crystallization driven by donor-acceptor interactions.

Conclusions:

  • The development of templated synthesis provides a route to desymmetrized pillararenes.
  • RD-P[6] exhibits tunable conformational properties and versatile host-guest capabilities.
  • This work offers new opportunities for designing complex molecular architectures and organic electronic materials.