分子识别是超分子化学领域的重点研究内容，近年来受到了众多研究者的广泛关注。阴离子在人类生活中的重要性，使得阴离子识别成为当今热点，因此设计出良好的阴离子选择性受体有着重要意义。由于阴离子结构具有多样性，并且识别过程依靠比较弱的非共价键作用力，使得受体的设计过程面临着很大挑战。本文论述了吡啶脲类和三甘醇类受体的合成、表征及其阴离子识别性质和主客体作用的研究。主要工作如下：

（1）合成并表征了吡啶脲类受体。以3',5'-二(吡啶-4-基)-[1,1'-联苯]-4-胺和2-硝基苯基异氰酸酯合成了中间产物1-(3',5'-二(吡啶-4-基)-[1,1'-联苯]-4-基)-3-(2-硝基苯基)脲(C₂₉H₂₁N₅O₃, I)，又将化合物I中的-NO₂在甲醇体系中通过Pd/C和水合肼还原成-NH₂，即中间产物1-(3',5'-二(吡啶-4-基)-[1,1'-联苯]-4-基)-3-(2-氨基苯基)脲(C₂₉H₂₃N₅O, II)，化合物II在乙腈体系中和三种含有不同取代基的异氰酸酯反应分别生成了1-(3',5'-二(吡啶-4-基)-[1,1'-联苯]-4-基)-3-(2-(3-(4-硝基苯基)脲)苯基)脲(C₃₆H₂₇N₇O₄，配体L¹)、1-(3',5'-二(吡啶-4-基)-[1,1'-联苯]-4-基)-3-(2-(3-(萘-1-基)脲)苯基)脲(C₄₀H₃₀N₆O₂，配体L²) 和1-(3',5'-二(吡啶-4-基)-[1,1'-联苯]-4-基)-3-(2-(3-(4-氯苯基)脲基)苯基)脲(C₃₆H₂₇ClN₆O₂，配体L³)。通过熔点测试、元素分析、红外光谱分析和¹H NMR、¹³C NMR进行表征，结果表明，合成产物皆为预期的目标产物。

（2）研究吡啶脲类受体与阴离子的相互作用。通过紫外-可见吸收光谱和荧光光谱探究了配体L¹~L³对不同阴离子的选择性识别能力，结果表明配体L¹可以选择性识别PO₄³⁻和SO₄²⁻，配体L²可以裸眼识别PO₄³⁻和CO₃²⁻，并且从荧光光谱中可以选择性识别CO₃²⁻，配体L³可以选择性识别PO₄³⁻、SO₄²⁻和CO₃²⁻。采用紫外-可见吸收光谱和荧光光谱通过Job曲线和滴定得到了配体与阴离子的结合比和结合常数。配体L¹与PO₄³⁻的结合比为1:1，结合常数为2.58×10⁴ M^-1；与SO₄²⁻的结合比为2:1，结合常数为3.16×10⁴ M^-1。配体L²与CO₃²⁻的结合比为1:1，结合常数为5.47×10⁴ M^-1。配体L³和PO₄³⁻的结合比为3:2，结合常数为1.78×10⁴ M^-1；与SO₄²⁻的结合比为2:1，结合常数为2.68×10⁴ M^-1；与CO₃²⁻的结合比为3:2，结合常数为5.54×10⁴ M^-1。

（3）合成并表征了三甘醇类受体及其单晶结构。用三乙二醇、对甲苯磺酰氯和4-硝基苯酚合成了1,8-双(对甲苯磺酰氧基)-3,6-二氧杂辛烷(C₂₀H₂₆O₈S₂, I)和1,8-双(4-硝基苯氧基)-3,6-二氧杂辛烷(C₁₈H₂₀N₂O₈, II)并培养了其单晶，用¹H NMR、¹³C NMR、红外、熔程、元素分析等方法进行了表征，结果表明化合物I和化合物II已成功制备，X-射线单晶衍射表明，化合物I的空间群为单斜晶系P2_1/c，通过C-H在乙二醇和苯环上的分子内C-H···π相互作用下形成特殊的S形构象，并由五个分子间C-H···O氢键构成三维网络结构。化合物II的空间群为三斜晶系P ，分子间无C-H···π相互作用，通过两个C-H···O氢键连接形成二维网络结构，并探索了它们特有的固态结构和弱相互作用。研究了化合物II和β-环糊精之间的主客体相互作用。通过¹H NMR、FT-IR和UV-vis光谱证实了化合物II与β-环糊精之间形成包合物，通过UV-vis滴定实验中的Job图和Hill曲线分析，计算了化合物II与β-环糊精之间的缔合常数和表观化学计量比，结果表明它们以1:2的结合比结合，且结合常数为5.31×10⁴ M^-1。

Molecular recognition is an important research area in supramolecular chemistry, which has attracted extensive attention of many researchers in recent years. The importance of anions in human life makes anion recognition a hot topic nowadays. Therefore, it is of great significance to design a good anion selective receptor. Due to the anion structure is diverse and the recognition process depends on the force of relatively weak non covalent bonds, which makes the design of receptors is facing great challenges. This paper discusses the synthesis, characterization, anion recognition and host guest interaction of pyridine urea and triethylene glycol receptors. The main work is as follows:

(1) Pyridine urea receptor was synthesized and characterized. Intermediate 1- (3',5'-bis(pyridin-4-yl)-[1,1'-biphenyl]-4-yl)-3-(2-nitrophenyl)urea (C₂₉H₂₁N₅O₃, I) was synthesized from 3',5'-bis(pyridin-4-yl)-[1,1'-biphenyl]-4-amine and 2-nitrophenyl isocyanate. Then -NO₂ in compound I was reduced to -NH₂ in methanol system through Pd/C and hydrazine hydrate, which is the intermediate 1-(3',5'-bis(pyridin-4-yl)-[1,1'-biphenyl]-4- yl)-3-(2-aminophenyl)urea(C₂₉H₂₃N₅O, II). Compound II reacted with three isocyanates containing different substituents in an acetonitrile system to generate 1-(3',5'-bis (pyridin-4-yl)-[1,1'-biphenyl]-4-yl)-3-(2-(3-(4-nitrophenyl)urea)urea(C₃₆H₂₇N₇O₄, ligand L¹), 1-(3',5'-bis(pyridin-4-yl)-[1,1'-biphenyl]-4-yl)-3-(2-(3-(naphthyl-1-yl)urea)urea (C₄₀H₃₀ N₆O₂, ligand L²) and 1-(3',5'-bis(pyridine-4-yl)-[1,1'-biphenyl]-4-yl)-3-(2-(3-(4-chlorophenyl) urea)urea(C₃₆H₂₇ClN₆O₂, ligand L³). Through melting range test, elemental analysis, FT-IR and ¹H NMR, ¹³C NMR, the results show that the synthetic products are the expected target products.

(2) The interaction between pyridine urea receptors and anions was studied. The selective recognition ability of ligands L¹~L³ to different anions was explored by UV-vis absorption spectrum and fluorescence spectrum. Ligand L³ can selectively recognize PO₄³⁻, SO₄²⁻ and CO₃²⁻. The binding ratio and binding constant of ligands and anion were obtained by Job plot curve and titration. The binding ratio of ligand L¹ to PO₄³⁻ is 1:1 and the binding constant is 2.58×10⁴ M^-1, the binding ratio with SO₄²⁻ is 2:1, and the binding constant is 3.16×10⁴ M^-1. The binding ratio of ligand L² to CO₃²⁻ is 1:1 and the binding constant is 5.47×10⁴ M^-1. The binding ratio of ligand L³ to PO₄³⁻ is 3:2 and the binding constant is 1.78×10⁴ M^-1; The binding ratio with SO₄²⁻ was 2:1 and the binding constant was 2.68×10⁴ M^-1; The binding ratio with CO₃²⁻ is 3:2 and the binding constant is K_a = 5.54×10⁴ M^-1。

(3) Triethylene glycol receptors and their single crystal structures were synthesized and characterized. 1,8-bis(p-toluenesulfonyloxy)-3,6-dioxaoctane(C₂₀H₂₆O₈S₂, I) and 1,8-bis(4- nitrophenoxy)-3,6-dioxaoctane (C₁₈H₂₀N₂O₈, II) were synthesized from triethylene glycol, p-toluenesulfonyl chloride and 4-nitrophenol and their single crystals were obtained. It was characterized by ¹H NMR, ¹³C NMR, FT-IR, melting point and elemental analysis. Result showed that compound I and compound II were successfully prepared. X-ray single crystal diffraction showed that the space group of compound I is monoclinic P2_1/c and formed a special sigmoid conformation through the intramolecular C-H···π interaction of C-H on ethylene glycol and benzene ring. The three-dimensional network structure is composed of five intermolecular C-H···O hydrogen bonds. The space group of compound II is triclinic system P . There is no C-H···π interaction between molecules. Two-dimensional network structures are formed through the connection of two C-H···O hydrogen bonds. Their unique solid structure and weak interaction are also explored. The host-guest chemistry between compounds II and β-cyclodextrin was studied. The inclusion complex between compounds II and β-cyclodextrin was confirmed by ¹H NMR, FT-IR and UV-vis spectra. Through the analysis of Job plot and Hill curve in UV-vis titration experiment, the association constant and apparent stoichiometric ratio of compound II and β-cyclodextrin were explored. The results showed that they were combined with a binding ratio of 1:2, and the binding constant is 5.31×10⁴ M^-1.

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