Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (6): 1330-1334.DOI: 10.6023/cjoc201411011 Previous Articles     Next Articles

Notes

对苯二甲酰氯桥联β-环糊精的合成及其对染料分子的协同键合

彭龙, 刘慧君, 胡趁, 孙允凯, 龙威   

  1. 南华大学化学化工学院 衡阳 421001
  • 收稿日期:2014-11-07 修回日期:2015-01-25 出版日期:2015-06-25 发布日期:2015-02-28
  • 通讯作者: 刘慧君 E-mail:liuhuijun@usc.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 11375084, 11305086 )资助项目.

Terephthaloyl Chloride Bridged Bis(β-cyclodextrin) and Their Synergetic Bonding Behaviors with Dyes

Peng Long, Liu Huijun, Hu Cheng, Sun Yunkai, Long Wei   

  1. College of Chemical Engineering, University of South China, Hengyang 421001
  • Received:2014-11-07 Revised:2015-01-25 Online:2015-06-25 Published:2015-02-28
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 11375084, 11305086).

A novel bridged bis(β-cyclodextrin) with rigid aromatic diamino tethers were synthesized by the reaction of terephthaloyl chloride with β-cyclodextrin. The novel bridged bis(β-cyclodextrin) was analyzed by 1H NMR, IR, UV and elemental analysis. The complex stability constants (KS) for the inclusion complexation of these bis(β-cyclodextrin) with several dyes possessing different shapes and electron intensities were determined by means of fluorescence and UV-Vis titrations at 25 ℃ in phosphate buffer solution (pH=7.2). The results show that the bridged bis(β-cyclodextrin) showed much higher binding ability. Compared with native β-cyclodextrin, the binding abilities of the bridged bis(β-cyclodextrin) upon inclusion complexation to TNS, ANS, AR, NR and RhB were increased 3.3, 15.3, 2.2, 12.5, and 5.8 times, respectively. The cooperative binding ability of the bis(β-cyclodextrin) was discussed from the viewpoints of size/shape-fit interaction and multiple recognition mechanism.

Key words: bridged bis(β-cyclodextrin), synergetic bonding, dyes, molecular recognition, supramolecular chemistry