含酚羟基缩氨基硫脲化合物的合成、表征及性能研究
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摘要
本论文共分四章:
第一章阐述了阴离子识别的最新研究进展,主要包括:(ⅰ)以羟基为识别位点的受体分子;(ⅱ)以硫脲为识别位点的受体分子;(ⅲ)水溶液中的阴离子识别研究;(ⅳ)具有专一选择性的阴离子识别研究。
第二章设计合成了4种偶氮水杨醛Schiff碱,利用紫外-可见吸收光谱和核磁共振氢谱系统考查了其在不同含水介质中与阴离子的识别作用。研究表明,在5%H2O-95%DMSO(v/v)体系中,向主体中加入F~-、Cl~-、Br~-、I~-、ClO_4~-、CH_3COO~-、H_2PO_4~-和HSO_4~-等八种阴离子,主体2~5均可以通过颜色的明显变化识别碱性较强的F~-、CH_3COO~-和H_2PO_4~-。而且对酸性较强的HSO_4~-通过质子化作用也具有独特的光谱响应。Bronst酸碱反应证明了主体化合物通过脱质子和质子化作用识别阴离子的过程。当体系的含水量提高到30%时,主体上的硫脲基团则与客体阴离子形成主-客体分子间的氢键进而通过颜色的变化高选择性的识别CH_3COO~-。
第三章设计合成了含有NH基团的杂环噻二唑硫酮类受体,并进行了初步的阴离子识别研究,结果表明:主体分子对阴离子的识别与其识别位点的位置有关。相比两个NH形成的线形受体分子3和钳形受体1来说,受体2中处于间位的两个杂环上的NH形成的钳形的结构,其空间构型更有利于以氢键的形式结合F~-、CH_3COO~-和H_2PO_4~-三种阴离子,从而达到裸眼识别阴离子的效果。
第四章本章主要分两部分,第一部分简要介绍了缩氨基硫脲类化合物的合成及应用研究进展。第二部分在室温下,以盐酸、硫酸做催化剂,通过简单的缩合反应合成了9个尚未见文献报道的偶氮芳基水杨醛缩氨基硫脲类化合物,并通过元素分析、红外光谱及核磁共振谱确证了其结构。初步的植物生长调节活性实验结果表明,该类化合物对油菜籽根的生长表现出高浓度下抑制、低浓度下促进的规律。
This paper includes four chapters:
Chapter One: This one is about the research of anion recognition in recent years. Including four parts: (ⅰ) receptors bearing phenolic hydroxy groups; (ⅱ) receptors bearing thiourea groups (ⅲ) anion recognition in water-containing system; (ⅳ) receptors recognized anions by highly selectivity from others.
Chapter Two: A series of schiffbase anion sensor bearing hodroxy and thiourea were synthesized by simple steps. It’s UV-vis spectra were taken in DMSO-H_2O binary solution. In 5%H_2O-95% DMSO (V/V) system, the receptors can recognize F~-, CH_3COO~-and H_2PO_4~- by their color change from grey to blue. As the ratio of water increases to 30%, the receptors showed color change only with CH_3COO~-, and no significant response to any of the other anions such as F~-, Cl~-, Br~-, I~-, H_2PO_4~- and ClO_4~-. The action of receptor-anion is supposed to the deprotonation acted on azophenolic OH and hydrogen bonding on thiourea worked together. Acidic anion hydrogen sulfate (HSO_4~-) can also be sensed by naked-eyes due to the protonation of receptors.
Chapter Three: Three anion sensors bearing heterocyclic NH were synthesized and the anion recognition research were taken by UV-vis spectra. The result indicated that the affinity is related to the space frame of the binding group.The receptor 2 can acted as F~-、CH_3COO~-and H_2PO_4~- anions sensor by naked eye due to its cleft structure.
Chapter Four: This one includes two parts: The first one is a brief review for the research and application values of thiosemicarbazone derivaties in recent years.The second one: Nine undocumented arylazo-salicylaldehyde thiosemicarbazone have been synthesized by simple method under catalysis of the acid. Their structures have been confirmed by IR, ~1H NMR, ~(13)C NMR and elemental analysis. The plant growth regulating activity tests showed that all compounds have good activity as plant growth regulator.
第一章阐述了阴离子识别的最新研究进展,主要包括:(ⅰ)以羟基为识别位点的受体分子;(ⅱ)以硫脲为识别位点的受体分子;(ⅲ)水溶液中的阴离子识别研究;(ⅳ)具有专一选择性的阴离子识别研究。
第二章设计合成了4种偶氮水杨醛Schiff碱,利用紫外-可见吸收光谱和核磁共振氢谱系统考查了其在不同含水介质中与阴离子的识别作用。研究表明,在5%H2O-95%DMSO(v/v)体系中,向主体中加入F~-、Cl~-、Br~-、I~-、ClO_4~-、CH_3COO~-、H_2PO_4~-和HSO_4~-等八种阴离子,主体2~5均可以通过颜色的明显变化识别碱性较强的F~-、CH_3COO~-和H_2PO_4~-。而且对酸性较强的HSO_4~-通过质子化作用也具有独特的光谱响应。Bronst酸碱反应证明了主体化合物通过脱质子和质子化作用识别阴离子的过程。当体系的含水量提高到30%时,主体上的硫脲基团则与客体阴离子形成主-客体分子间的氢键进而通过颜色的变化高选择性的识别CH_3COO~-。
第三章设计合成了含有NH基团的杂环噻二唑硫酮类受体,并进行了初步的阴离子识别研究,结果表明:主体分子对阴离子的识别与其识别位点的位置有关。相比两个NH形成的线形受体分子3和钳形受体1来说,受体2中处于间位的两个杂环上的NH形成的钳形的结构,其空间构型更有利于以氢键的形式结合F~-、CH_3COO~-和H_2PO_4~-三种阴离子,从而达到裸眼识别阴离子的效果。
第四章本章主要分两部分,第一部分简要介绍了缩氨基硫脲类化合物的合成及应用研究进展。第二部分在室温下,以盐酸、硫酸做催化剂,通过简单的缩合反应合成了9个尚未见文献报道的偶氮芳基水杨醛缩氨基硫脲类化合物,并通过元素分析、红外光谱及核磁共振谱确证了其结构。初步的植物生长调节活性实验结果表明,该类化合物对油菜籽根的生长表现出高浓度下抑制、低浓度下促进的规律。
This paper includes four chapters:
Chapter One: This one is about the research of anion recognition in recent years. Including four parts: (ⅰ) receptors bearing phenolic hydroxy groups; (ⅱ) receptors bearing thiourea groups (ⅲ) anion recognition in water-containing system; (ⅳ) receptors recognized anions by highly selectivity from others.
Chapter Two: A series of schiffbase anion sensor bearing hodroxy and thiourea were synthesized by simple steps. It’s UV-vis spectra were taken in DMSO-H_2O binary solution. In 5%H_2O-95% DMSO (V/V) system, the receptors can recognize F~-, CH_3COO~-and H_2PO_4~- by their color change from grey to blue. As the ratio of water increases to 30%, the receptors showed color change only with CH_3COO~-, and no significant response to any of the other anions such as F~-, Cl~-, Br~-, I~-, H_2PO_4~- and ClO_4~-. The action of receptor-anion is supposed to the deprotonation acted on azophenolic OH and hydrogen bonding on thiourea worked together. Acidic anion hydrogen sulfate (HSO_4~-) can also be sensed by naked-eyes due to the protonation of receptors.
Chapter Three: Three anion sensors bearing heterocyclic NH were synthesized and the anion recognition research were taken by UV-vis spectra. The result indicated that the affinity is related to the space frame of the binding group.The receptor 2 can acted as F~-、CH_3COO~-and H_2PO_4~- anions sensor by naked eye due to its cleft structure.
Chapter Four: This one includes two parts: The first one is a brief review for the research and application values of thiosemicarbazone derivaties in recent years.The second one: Nine undocumented arylazo-salicylaldehyde thiosemicarbazone have been synthesized by simple method under catalysis of the acid. Their structures have been confirmed by IR, ~1H NMR, ~(13)C NMR and elemental analysis. The plant growth regulating activity tests showed that all compounds have good activity as plant growth regulator.
引文
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