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
收稿日期: 2014-11-07
修回日期: 2015-01-25
网络出版日期: 2015-02-28
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
Received date: 2014-11-07
Revised date: 2015-01-25
Online published: 2015-02-28
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 11375084, 11305086).
实验以β-环糊精和对苯二甲酰氯为原料, 合成了一种新型刚性结构的桥联环糊精——1,4-二甲酰胺基苯桥联β-环糊精, 并通过1H NMR、红外和紫外以及元素分析等对其结构进行了表征. 采用荧光光谱滴定法分别测定了该桥联环糊精与几种具有不同形状和电子密度的染料分子在25 ℃磷酸缓冲溶液(pH=7.20)中的包结配位稳定常数KS. 结果表明, 桥联环糊精的键合能力远远增强, 桥联环糊精与天然β-环糊精相比, 对TNS, ANS, AR, NR和RhB的包结稳定常数分别提高了3.3, 15.3, 2.2, 12.5和5.8倍. 从主-客体间的尺寸匹配关系和多重识别机理等方面探讨了桥联环糊精对客体分子的协同键合作用.
彭龙 , 刘慧君 , 胡趁 , 孙允凯 , 龙威 . 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[J]. 有机化学, 2015 , 35(6) : 1330 -1334 . DOI: 10.6023/cjoc201411011
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.
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