设计合成了3种新型间苯二甲酰腙类化合物,利用UV-Vis及~1H NMR等测试技术考察了其与F~-、Cl~-、Br~-、I~-、CH_3COO~-、HSO_4~-、H_2PO_4~-、ClO_4~-等阴离子之间的相互作用. 结果表明,主体分子4a(双对硝基苯并呋喃甲醛间苯二甲酰腙)在DMSO溶液中对F~-和CH_3COO~-有显著识别效果,溶液颜色由黄色分别变为深黄色和棕红色. 通过~1H NMR表征及质子溶剂效应进一步证明,主体分子与阴离子之间是以氢键作用方式相结合. Job曲线表明,主客体间形成1:1型氢键络合物. 基于实验结果,探讨了主客体间形状和体积匹配对识别能力的影响以及主客体之间的识别模式.
Three novel 1,3-benzyldiacyl hydrazone derivatives (4a ～4c) were designed and synthesized. The binding properties of the receptor with anions such as F~- , Cl~-, Br~-, I~-, CH_3 COO~- , HSO_4~- , H_2 PO_4~- and ClO_4~- in DMSO were investigated by UV-Vis and ~1H NMR. As a result, receptor 4a(1,3-benzyldi(4-nitro-pheyl-2-furfuraldehyde) methacylhydrazone) can recognize anions through hydrogen bonding in DMSO solutions. A clear color change was observed from yellow to dark yellow and pale red upon addition of F~- and CH_3 COO_~-· ~-H NMR titration and solvation effect confirm hydrogen bonding interaction between the receptor and the anions. Job curve indicates that a 1:1 stoichiometry complex is formed between the receptor and the two kinds of anions. Based on the above results, the recognition binding mode was discussed. The molecular recognition ability was discussed in terms of the size and shape-fit as well as the recognition model between host and guest molecules.
参考文献
| [1] | Shao J,Lin H,Yu M,Lin H K.Talanta[J],2008,75:551 |
| [2] | Zhang Y H,Yin Z M,He J Q,Cheng J P.Tetrahedron Lett[J],2007,48:6 039 |
| [3] | Shang X,Lin H,Lin H K.J Flu Chem[J],2007,128:530 |
| [4] | ZHANG Y M,Cao C,Wei W,Wei T B.Chinese J Chem[J],2007,25:709 |
| [5] | XU Wei-Xia(徐维霞),ZHANG You-Ming(张有明),WEI Tai-Bao(魏太保).Chinse J Appl Chem(应用化学)[J],2008,25(12):1 460 |
| [6] | REN Hai-Xian(任海仙),TANG Jing(唐静),WEI Tai-Bao(魏太保),ZHANG You-Ming(张有明).Chinese J Inorg Chem(无机化学学报)[J],2007,23(11):1 907 |
| [7] | Zhang Y M,Qing J D,Li Q,Wei T B.J Flu Chem[J],2006,127:1 222 |
| [8] | Nie L,Li Z,Han J,Zhang X,Yang R,Liu W X,Wu F Y,Xie J W,Zhao Y F,Jiang Y B.J Org Chem[J],2004,69:6 449 |
| [9] | YU Ming(郁铭),LIN Hai(林海),LIN Hua-Kuan(林华宽).Chem J Chinese Univ(高等学校化学学报)[J],2007,28(1):83 |
| [10] | SHI Da-Qing(史达清),WANG Hai-Ying(王海营),YANG Fang(杨芳),LI Xiao-Yue(李小跃).Acta Chim Sin(化学学报)[J],2007,65(16):1 713 |
| [11] | WANG Jing-Xian(王进贤),CHEN Ji-Chou (陈继畴),LI Zhong-Jie(李众杰).Chinese Sci Bull(科学通报)[J],1966,17(9):419 |
| [12] | FAN Neng-Ting(樊能廷).Synthetic Organic Literary(有机合成事典)[M].Beijing(北京):Beijing Institute of Technology Press(北京理工大学出版社),1995:349 |
| [13] | LONG De-Qing(龙德清),CHEN Sheng-Sheng(陈胜胜),LI De-Jiang(李德江).J Jiangxi Normal Univ(江西师范大学学报)[J],2006,30(4):372 |
| [14] | WU Fang-Ying(吴芳英),HU Mei-Hua(胡美华),TAN Xiao-Fang(谭晓芳),ZHAO Yong-Qiang(赵永强),JI Zhao-Jun(纪昭君),LI Li(李丽).Chem J Chinese Univ(高等学校化学学报)[J],2005,26(8):1 415 |
| [15] | Liu Y,Kang S Z,Li L.Supramol Chem[J],2002,14(4):329 |
- 下载量()
- 访问量()
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%