间苯二甲酰腙分子钳的合成及阴离子识别研究

摘要/Abstract

摘要：

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考察了其与F^-、Cl^-、Br^-、I^-、CH₃COO^-、HSO₄^-、H₂PO4-、ClO4-阴离子的相互作用。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CH₃COO-有显著识别效果，溶液颜色由黄色变为深黄色和棕红色。通过¹H NMR滴定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大小匹配对识别能力的影响以及主客体之间的识别模式。

关键词: 分子钳，阴离子识别，紫外-可见吸收光谱，间苯二甲酰腙

Abstract:

Three novel 1,3-benzyldiacyl hydrazone derivatives(4a~4c) have been designed and synthesized in the paper.The binding properties of the receptors with anions such as F-, Cl-, Br-, I-, CH3COO-, HSO4-, H2PO4- and ClO4- in DMSO were investigated by UV-Vis and 1H NMR spectroscopy. As a result, receptor 4a(1,3-benzyldi (4-nitropheyl-2-furfuraldehyde) methacylhydrazone) can recognize anions through hydrogen binding in DMSO solutions. A clear color chang was observed from yellow to dark yellow and pale red upon addition of F- and CH3COO- . 1H NMR titrations and salvation effect confirm hydrogen bonding interaction between the receptors and anions. Job curve indicates that a 1:1 stoichiometry complex is formed between the receptors and the two anions. Based on the above results, the recognition binding mode were discussed. molecules. The molecular recognition ability is discussed in terms of the size and shape-fit as well as the recognition model between host and guest molecules.

Key words: molecular tweezer,anion recognition,UV-Vis absorption spectrum,benzyldiacyl hydrazone

中图分类号:

O611.5

张有明, 王爱霞, 冷艳丽, 王雅琳, 魏太保. 间苯二甲酰腙分子钳的合成及阴离子识别研究[J]. 应用化学, 2009, 26(11): 1253-1258.

ZHANG You-Ming, WANG Ai-Xia, LENG Yan-Li, WANG Ya-Lin, WEI Tai-Bao*. 1,3-benzyldiacyl hydrazone Tweezers Receptors: Synthesis and Anions Recognition Properties[J]. Chinese Journal of Applied Chemistry, 2009, 26(11): 1253-1258.

间苯二甲酰腙分子钳的合成及阴离子识别研究

1,3-benzyldiacyl hydrazone Tweezers Receptors: Synthesis and Anions Recognition Properties

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