Scholarlink

<p>The development of macrocyclic hosts with high-affinity 1:2 recognition capabilities is crucial for advancing supramolecular chemistry and its applications. While cucurbit[8]uril (CB[8]) has long been recognized for its unparallel 1:2 binding affinity, its limitations—including poor solubility, difficulty to modify and lack of optical activity—have hindered broader utilization. Here, we introduce a class of enantiopure chiral macrocycles, <i>RRRR</i>- or <i>SSSS</i>-corral[4]BINOL (C[4]Bs), which exhibit remarkable 1:2 recognition properties in water that are comparable or even surpass CB[8]. Using UV-Vis, fluorometric, and isothermal titration calorimetry (ITC), we demonstrate that C[4]Bs form stable homoternary complexes with 11 singly positively charged planar aromatic guests, with binding affinities up to 10<sup>17 </sup>M<sup>−2</sup>. These ultrahigh affinities make C[4]Bs versatile alternatives to CB[8], offering advantages such as superior water-solubility, ease of structural modification, and strong fluorescence. Furthermore, the unique chiral nature of C[4]Bs enables efficient fluorescent discrimination of chiral substrates and chirality transfer to non-chiral dyes, resulting in strong circularly polarized luminescence (CPL) with |<i>g</i><sub>lum</sub> | values up to 1.1 ×10<sup>−2</sup>. This study establishes C[4]Bs not only as powerful hosts for aqueous-phase supramolecular complexation but also as a promising platform for developing chiral functional materials.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Chiral macrocycles forming high-affinity host-guest homoternary complexes for chiral discrimination and amplified circularly polarized luminescence

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2025年11月4日

查看全文
  • Rong Fu,
  • Fang-Yuan Chen,
  • Le Dai,
  • Dai-Yuan Li,
  • Qing-Yu Zhao,
  • Si-Dan Guo,
  • Zi-Hang Song,
  • Li-Bo Jing,
  • Heng Wang,
  • Xiaopeng Li,
  • Dong-Sheng Guo,
  • Kang Cai

摘要

The development of macrocyclic hosts with high-affinity 1:2 recognition capabilities is crucial for advancing supramolecular chemistry and its applications. While cucurbit[8]uril (CB[8]) has long been recognized for its unparallel 1:2 binding affinity, its limitations—including poor solubility, difficulty to modify and lack of optical activity—have hindered broader utilization. Here, we introduce a class of enantiopure chiral macrocycles, RRRR- or SSSS-corral[4]BINOL (C[4]Bs), which exhibit remarkable 1:2 recognition properties in water that are comparable or even surpass CB[8]. Using UV-Vis, fluorometric, and isothermal titration calorimetry (ITC), we demonstrate that C[4]Bs form stable homoternary complexes with 11 singly positively charged planar aromatic guests, with binding affinities up to 1017 M−2. These ultrahigh affinities make C[4]Bs versatile alternatives to CB[8], offering advantages such as superior water-solubility, ease of structural modification, and strong fluorescence. Furthermore, the unique chiral nature of C[4]Bs enables efficient fluorescent discrimination of chiral substrates and chirality transfer to non-chiral dyes, resulting in strong circularly polarized luminescence (CPL) with |glum | values up to 1.1 ×10−2. This study establishes C[4]Bs not only as powerful hosts for aqueous-phase supramolecular complexation but also as a promising platform for developing chiral functional materials.