物理化学学报 >> 2006, Vol. 22 >> Issue (09): 1065-1070.doi: 10.1016/S1872-1508(06)60046-6

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修饰β-环糊精/4-(N,N-二甲氨基)-苯甲酸-2′-乙基己基酯笼型包结物研究

杜新贞;周嵘;陶小娟;王芳平;陈慧   

  1. (西北师范大学化学系, 兰州 730070)
  • 收稿日期:2006-03-03 修回日期:2006-03-29 发布日期:2006-09-04
  • 通讯作者: 杜新贞 E-mail:duxz@nwnu.edu.cn

A Study of Cage-type Inclusion Complexes of Modified β-cyclodextrins with 2′-ethylhexyl-4-(N,N-dimethylamino)-benzoate

DU Xin-Zhen;ZHOU Rong;TAO Xiao-Juan;WANG Fang-Ping;CHEN Hui   

  1. (Department of Chemistry, Northwest Normal University, Lanzhou 730070, P. R. China)
  • Received:2006-03-03 Revised:2006-03-29 Published:2006-09-04
  • Contact: DU Xin-Zhen E-mail:duxz@nwnu.edu.cn

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摘要： 用分子光谱法研究了甲基-β-环糊精(M-CD)和羟丙基-β-环糊精(HP-CD)与4-(N,N-二甲氨基)-苯甲酸-2′-乙基己基酯(EHDAB)分子间的包结作用. 结果表明, 柔性的2′-乙基己基和刚性的芳香端都包结在M-CD和HP-CD空腔中, 形成了2:1笼型主-客体包结物. 疏水性2′-乙基己基在包结物的热力学稳定性中起重要作用, 亲水性M-CD和HP-CD将EHDAB增溶在水中, 提高了EHDAB分子的紫外吸收程度, M-CD和HP-CD空腔抑制了光诱导EHDAB分子内扭转电荷转移, 显著提高了EHDAB的光化学稳定性, 增强了其抗氧化性, 降低了酸碱性水解程度, 包结物的热稳定性与所用主体环糊精相当.

关键词: 紫外吸收剂, 环糊精, 主-客体包结物, 光化学稳定性, 分子内扭转电荷转移, 抗氧化性

Abstract: The inclusion of 2′-ethylhexyl-4-(N, N-dimethylamino)-benzoate (EHDAB) into methylated β-cyclodextrin (M-CD) and 2′-hydroxypropyl-β-cyclodextrin (HP-CD) was examined using molecular spectra. Both the flexible 2′-ethylhexyl chain and the rigid aromatic moiety of EHDAB were encapsulated within the cavity of M-CD and HP-CD, respectively. EHDAB was stabilized within the 2:1 cage-type host-guest inclusion complexes. The hydrophobic 2′-ethylhexyl tail greatly contributes to the extraordinarily stable complexes. M-CD and HP-CD increased the water solubility of EHDAB. The enhanced absorbance of EHDAB was obtained, and the photo-induced twisted intramolecular charge transfer of EHDAB was greatly suppressed by the restricted shape and size of the cavity. The photodegradation of EHDAB was markedly reduced in aqueous solution. EHDAB was still stable in alkaline solutions of M-CD and HP-CD. Anti-oxidation and thermal stability were appreciably promoted at the same time.

Key words: UV absorber, Cyclodextrins, Host-guest inclusion complexes, Photostability, Twisted intramolecular charge transfer, Anti-oxidation