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March 27, 2026Organic Letters2 citations

Cyclicurilarenes: Hybridizing Bambusurils with Macrocyclic Arenes

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MWMingyue WenWLWenhao LinXSXixian Sun

Key Points

  • The aim is to create cyclicurilarene receptors with enhanced adaptability for various substrates.
  • Coupling 2,4-dimethylglycoluril with bis(bromomethyl)-substituted dimethoxybenzene through nucleophilic substitution.
  • Synthesis of four- and six-membered cyclicurilarenes with alternating units.
  • Characterization of configurations and binding interactions in solid state and solution.
  • Synthesis of novel cyclicurilarenes with conformational flexibility.
  • Distinct acetonitrile positions related to anti/syn-configurations observed.
  • Inward-oriented glycoluril establishes hydrogen bonds with alanine derivatives in chloroform.

Abstract

Our cyclicurilarene receptor family has been extended by coupling of 2,4-dimethylglycoluril with bis(bromomethyl)-substituted dimethoxybenzene through nucleophilic substitution, yielding macrocycles with conformational flexibility that can adapt to different-sized substrates, resembling bambusurils. Anti/syn-configurations of the two glycoluril units in “Ding”-shaped cyclicurilarenes induce distinct acetonitrile positions in the solid state, and inward-oriented glycoluril forms intracavity hydrogen bonds with alanine derivative in chloroform. Four- and six-membered cyclicurilarenes featuring alternating dimethoxybenzene and glycoluril units were synthesized.

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Cite This Study

Wen et al. (2026) studied this question.

synapsesocial.com/papers/69c61ff615a0a509bde185d0https://doi.org/10.1021/acs.orglett.6c00209
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