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<p>Achieving ultrahigh-affinity molecular recognition in aqueous media remains a key challenge in supramolecular chemistry. We report the synthesis of (+)-CA-C[4]B, a water-soluble chiral macrocycle derived from enantiopure BINOL, featuring eight carboxylate groups on its rims to enhance cavity depth and binding affinity. In aqueous media, (+)-CA-C[4]B exhibits ultrahigh 1:1 host-guest binding affinities up to 10<sup>13</sup> M<sup>−1</sup> and 1:2 binding affinities up to 10<sup>16</sup> M<sup>−2</sup>. Notably, it supports dual-mode 1:2 binding: face-to-face for planar aromatic guests and head-to-head for spherical guests like adamantane. Combined with its high recognition affinities, superior fluorescence (quantum yield 43%) and circularly polarized luminescence (|<i>g</i><sub>lum</sub>| = 2.6 × 10<sup>−3</sup>), (+)-CA-C[4]B offers transformative potential for chiral supramolecular materials.</p>

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Ultrahigh-affinity 1:1 and 1:2 molecular recognition in water by a rim-carboxylated chiral corral[4]BINOL

  • 期刊论文

  • 发表日期：

    2025年11月3日

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  • Li-Bo Jing,
  • Ruiguo Wang,
  • Rong Fu,
  • Hui-Tao Zheng,
  • Jinlei Zhou,
  • Qing-Yu Zhao,
  • Zi-Hang Song,
  • Dong-Sheng Guo,
  • Kang Cai

摘要

Achieving ultrahigh-affinity molecular recognition in aqueous media remains a key challenge in supramolecular chemistry. We report the synthesis of (+)-CA-C[4]B, a water-soluble chiral macrocycle derived from enantiopure BINOL, featuring eight carboxylate groups on its rims to enhance cavity depth and binding affinity. In aqueous media, (+)-CA-C[4]B exhibits ultrahigh 1:1 host-guest binding affinities up to 1013 M−1 and 1:2 binding affinities up to 1016 M−2. Notably, it supports dual-mode 1:2 binding: face-to-face for planar aromatic guests and head-to-head for spherical guests like adamantane. Combined with its high recognition affinities, superior fluorescence (quantum yield 43%) and circularly polarized luminescence (|glum| = 2.6 × 10−3), (+)-CA-C[4]B offers transformative potential for chiral supramolecular materials.