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<p>Anion-carbonyl interaction is a newly developed non-covalent bond, and its application as a driving force in supramolecular chemistry deserves exploration. Herein, a series of barbiturate-containing macrocycles were synthesized using macrocycle-to-macrocycle transformation or one-pot macrocyclization. Various structural conformations arising from the interplay of non-aromatic barbiturate and benzene rings through N–C rotations in solution were revealed. The macrocycles featuring carbonyl donors and acceptors resulted in unique self-assembly structures and host-guest complexes in the crystalline state. The [3+3] macrocycle <b>7a</b> was applied as a host molecule to investigate the complexation with anions by <sup>13</sup>C nuclear magnetic resonance (NMR) titrations, which showed selective binding towards malonate with an association constant of <i>K</i><sub>a(1:1)</sub> = 13.2 ± 1.57 M<sup>−1</sup>. Multiple anion-carbonyl interactions between <b>7a</b> and malonate were revealed by density functional theory (DFT) optimization of the complex.</p>

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Barbiturate-containing macrocycles: synthesis, structure and anion recognition through anion-carbonyl interactions

  • 期刊论文

  • 发表日期：

    2025年4月15日

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  • Jun Zhu,
  • Xu-Dong Wang,
  • Yu-Fei Ao,
  • Qi-Qiang Wang,
  • De-Xian Wang

摘要

Anion-carbonyl interaction is a newly developed non-covalent bond, and its application as a driving force in supramolecular chemistry deserves exploration. Herein, a series of barbiturate-containing macrocycles were synthesized using macrocycle-to-macrocycle transformation or one-pot macrocyclization. Various structural conformations arising from the interplay of non-aromatic barbiturate and benzene rings through N–C rotations in solution were revealed. The macrocycles featuring carbonyl donors and acceptors resulted in unique self-assembly structures and host-guest complexes in the crystalline state. The [3+3] macrocycle 7a was applied as a host molecule to investigate the complexation with anions by 13C nuclear magnetic resonance (NMR) titrations, which showed selective binding towards malonate with an association constant of Ka(1:1) = 13.2 ± 1.57 M−1. Multiple anion-carbonyl interactions between 7a and malonate were revealed by density functional theory (DFT) optimization of the complex.