Three novel calix[4]benzocrowns with π-conjugate azo groups on sidechains were designed and synthesized in ideal yields. Their structures and conformations were characterized by IR, 1H NMR, ESI–MS, elemental analysis. Their complexation abilities for dyes were investigated by liquid–liquid extraction experiments, complexation UV–Vis spectra and complexation ESI–MS spectra. The complexation experimental results suggested that they possessed excellent extraction abilities towards dyes. The highest extraction percentage of compound 3a for neutral red was 89.5 %. The complexation UV–Vis spectra of compounds 3a–c with four dyes indicated the 1:1 complexes between host and guest in DMSO solution. The association constant of compound 3b with OI was as high as 3.93 × 106 M−1. The complexation ESI–MS spectrum of compound 3c for Neutral red also supported the 1:1 complexes of host and guest. The complexation experiments showed these novel calix[4]arene receptors possess excellent complexation capabilities for dyes.
本研究设计并合成了侧链上带有π-共轭偶氮基团的三种新型
钙并[4]苯并[4]酰胺,产量理想。通过红外光谱、1H NMR、ESI-MS 和元素分析对它们的结构和构象进行了表征。通过液液萃取实验、络合紫外可见光谱和络合 ESI-MS 图谱研究了它们与
染料的络合能力。络合实验结果表明,它们对
染料具有极佳的萃取能力。化合物 3a 对
中性红的萃取率最高,达到 89.5%。化合物 3a-c 与四种
染料的络合紫外可见光谱显示,在
DMSO 溶液中,主客体之间的络合比例为 1:1。化合物 3b 与 OI 的结合常数高达 3.93 × 106 M-1。化合物 3c 与
中性红的络合 ESI-MS 图谱也支持主客体形成 1:1 的络合物。络合实验表明,这些新型
钙[4]炔受体对
染料具有出色的络合能力。