新型N-酰胺基（硫）脲类中性阴离子受体
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摘要
分子识别是超分子化学领域研究的热点之一。因阴离子识别对于揭示生命过程中化学反应的本质具有重要意义,阴离子识别和传感研究备受关注。基于氢键作用的中性受体分子逐渐成为阴离子受体分子发展之主流,良好的阴离子识别性能是设计中性受体时考虑的关键因素;而评价受体性能的核心指标就是选择性和灵敏度。目前,提高中性受体阴离子结合性能的主要策略有四条:(1)增加氢键结合位点;(2)提高结合位点质子酸性;(3)借助静电引力的协同作用;(4)引入变构原理。本论文以N-酰胺基硫脲作为有效的阴离子结合位点,在传统阴离子中性受体研究的基础上,致力于探寻提高中性受体阴离子识别性能的新思路,并成功地构建了一系列具有良好阴离子识别性能的(硫)脲类中性受体,可以高效、高选择性乃至可于高竞争性水溶液中结合阴离子。论文共分为五章,分别包含以下主要内容:
第一章为前言。首先简要介绍了超分子化学的研究现状和发展趋势;然后评述分子识别研究中基于氢键作用的中性阴离子受体的发展近况,着重论述中性受体设计时面临的挑战和当前的应对策略;最后,以此为基础、并基于本实验室已有的研究积累,提出本论文的研究设想。
第二章为实验部分。详细介绍论文工作中所涉及主要试剂、仪器和受体分子的合成方法与结构鉴定。包括N-脂肪酰胺基-N'-(取代苯基)硫脲、聚-N-脂肪酰胺基-N'-苯基硫脲、N-乙酰胺基-N'-苯基脲、N-异烟酰胺基-N'-(取代苯基)硫脲和N-(2-(羟基)苄亚胺基)-N'-苯基脲等近三十种化合物。
第三章合成了一类具有良好阴离子识别性能的N-脂肪酰胺基-N'-(取代苯基)-硫脲类中性受体,运用吸收光谱法研究了其与阴离子的结合、作用模式和影响因素。发现N-酰胺基端为脂肪酰胺基时,硫脲-NH酸性降低,但受体与阴离子的结合常数却有所提高。醇效应实验和CD_3CN中的核磁滴定表明受体分子与阴离子间通过氢键作用维系。分子两端取代基对受体-阴离子的结合产生不同影响:N'-苯基端取代基的推拉电子能力影响受体与阴离子结合能力;N-酰胺基端取代基则影响受体-阴离子结合物的吸收光谱形状。玻片表面固载聚-N-酰胺基-N'-苯基硫脲受体,利用接触角研究了受体与阴离子间的相互作用。本章还提出了提高受体对阴离子结合选择性的两条新途径:一是受体具有适宜的结构时,适当降低硫脲-NH的酸性以减小受体对阴离子的结合能力,可改善受体对某种阴离子结合的选择性;二是运用分子印迹技术,提高受体与阴离子结合的选择性。
第四章合成了N-异烟酰胺基-N'-(取代苯基)硫脲类阴离子受体。受体分子以酰胺基硫脲为结合位点,吡啶环的引入可提高受体在水溶液中的溶解性。研究发现受体具有极强的阴离子结合性能,MeCN中与阴离子的结合常数大于10~7Lmol~(-1)数量级,可将阴离子识别拓展至H_2O-MeCN混合溶剂中。核磁滴定表明受体分子与阴离子间系氢键作用,无脱质子过程发生。首次实现了简单中性受体分子在纯水介质中的阴离子有效结合。基于酰胺-NH质子核磁位移的相关分析表明,分子中的吡啶环相当于含有强吸电子取代基的苯环,酰胺-NH质子足够的酸性,是受体具有良好阴离子结合性能的重要原因。但更为重要的因素在于极性溶液中分子两端的疏水芳基在疏水作用力下可相互靠近,形成一个有利于阴离子结合的疏水微环境,这是受体在水溶液仍保持较好的阴离子结合能力的关键因素。本研究为水溶液中中性阴离子受体的设计提供了一种新的策略,可望为基于硫脲基团的有机催化剂的设计提供借鉴。
第五章设计合成了一种新型的同源协同变构型荧光受体:N-(2-(羟基)苄亚胺基)-N'-苯基脲,对F~-表现出高的响应灵敏度和结合选择性:F~-导致受体MeCN溶液颜色由无色转变为黄色,荧光增强300余倍;CH_3CO_2~-和H_2PO_4~-等其它阴离子存在时溶液颜色均无此变化,荧光增强不足20倍。实验发现,分子中含有的两个阴离子结合位点,酚羟基-OH和两个脲基氮氢-NH,与F~-发生了分步反应:第一个F~-与受体酚羟基-OH结合,导致-OH脱质子,受体发生构型变化,增强了第二个F~-与受体脲基氮氢-NH的氢键结合。同时受体分子结构的柔性确保第一步反应对第二步反应产生的协同促进作用能顺利进行。而受体与CH_3CO_2~-和H_2PO_4~-等阴离子的氢键结合一步完成,脲基氮氢-NH的阴离子氢键结合能力较硫脲弱,因此受体与CH_3CO_2~-和H_2PO_4~-等的结合能力也较弱。可见分步结合和变构效应是受体对F~-具有强的结合能力和高选择性的关键。本实验为探索高灵敏和高选择性阴离子受体分子的设计作出了有益的尝试。
最后于附录部分总结了本论文的创新点,并展望后续研究工作。
Molecular recognition is one of the subjects receiving continuous interests in supramolecular chemistry. Since anions play a fundamental role in disclosing the essence of biological processes, anion recognition and sensing by synthetic receptors has received increasing recent attention. Especially, the development of neutral receptors based on hydrogen bonding has become a must for receptors of excellent anion-recognition ability. Selectivity and sensitivity are the key parameter in evaluating anion receptors, several strategies have been developed to improve anion-recognition ability of neutral receptors by incorporating more binding sites in a suitable arrangement, increasing the acidity of the hydrogen bonding donors, cooperating with electrostatic interactions, and utilizing allosteric interaction. In this thesis, a series of neutral anion receptors were designed and synthesized, employing the N-amido(thio)urea as an efficient binding site. Interactions of the binding moiety and anions were investigated in order to explore promising new approaches for improving anion-recognition ability of the neutral receptors.
The dissertation consists of five chapters summarized as the following.
Chapter 1 presents a general introduction to supramolecular chemistry relating to the researches in the development of neutral anion receptors based on hydrogen bond. Emphases were focused on the challenges existing in the design of neutral receptors, and the strategy resolving these problems. The objectives of this dissertation were proposed.
Chapter 2 describes the syntheses and characterization of ca. 30 receptors designed in this thesis for anion recognition, including N-aliphaticamido-N'-(substituted)phenyl (thio)urea, poly-(N-amido-N'-phenyl)thiourea, N-(isonicotinamido)-N'-(substitutedphenyl)thioureas, and N-(2-(hydroxyl)benzylimino)-N'-phenylurea. The equipments, materials and methods involved in this dissertation are also described.
Chapter 3 reports the anion binding of N-aliphaticamido-N-(substituted)phenyl (thio)urea. The N-amidothiourea binding site was employed on the basis of our previous work that showed a substantially enhanced anion binding affinity compared to the traditional N-phenylthiourea binding site. It was found that when the the acidity of thioureido -NH protons in N-aliphaticamido-N-phenylthioureas was lower than that in N-benzamido-N'-phenylthioureas, yet the anion binding ability was stronger. Protic solvent competition in MeCN by MeOH and ~1H NMR titrations in CD_CN supported the hydrogen bond interaction of the receptor with anion. The substituent of the N '-phenyl ring and of the N-amido group exist different influence on anion biding, the former remarkably influencing anion binding, while the latter affecting more to the absorption spectra of the receptor upon anion binding. Polymerizable N-amidothiourea-based receptors were polymerized and were fixated on the surface of glass. Contact angle measurements were used to understand interactions of anion and poly-N-amidothiourea-based receptors. Two new approaches were attempted to increase selectivity in anion binding, to properly decrease the acidity of thioureido -NH protons in a receptor with suitable structure, and to apply the molecular imprinting technology.
Chapter 4 presents the design of N-(isonicotinamido)-N'-(substituted-phenyl) thioureas as simple neutral anion receptors capable of binding anion in aqueous solutions. A pyridine terminal was chosen to improve water solubility of the receptor molecules. These receptors showed substantial anion-binding ability in MeCN solution with binding constants of 10~7 L mol~(-1) order of magnitude. Significantly is that they showed sensitive response to anions such as CH_3CO_2~- in aqueous solutions with binding constants of 10~3 L mol~(-1) order of magnitude. The hydrogen bonding interaction between the receptor and anion was proved by ~1H NMR titration in CD_3CN, with no deprotonation occurring. The pyridine ring was shown to correspond to a phenyl ring bearing an electron withdrawing para-substituent of Hammett constant 0.75, which implied that the amido -NH is acidic enough to afford the capability of anion binding in aqueous solutions. Although this seems to point to the critical role of the acidity of the amido -NH proton, we showed that it was instead the less polar hydrophobic microenvironment afforded by the approaching of two aromatic rings in these receptors driven by hydrophobic interaction that promoted the anion binding in aqueous solutions. A new approach was provided for designing neutral receptors based on hydrogen bonding for anion binding in aqueous solutions by taking into account the receptor molecular conformation.
Chapter 5 reports a homotropic allosteric receptor, N-(2-(hydroxyl)benzylimino)-N'-phenylurea, highly selective and sensitive for F~-. A moderate color change from colorless to yellow and a drastic fluorescence enhancement of c.a. 300 fold were observed when F~- is added to the receptor solution in MeCN, whereas other anion led to no color change and tiny fluorescence enhancement of less than 20 fold. The receptor bears three distinct hydrogen bonding groups, one phenolic -OH and two ureido NHs, which bind stepwise to F~-. Binding of the first F~- had a consequence of that of the subsequent interaction of the second F~-. The first F~- binding to the receptor's phenolic -OH resulted in the deprotonation and a conformation change in the receptor that reinforced its next binding to F~-. Differing from the stepwise binding to F~-, the receptor bound other anions such as CH_3CO_2~- and H_2PO_4~- in a single step via -OH and ureido -NH protons in a 1:1 stoichiometry. Since the acidity of the ureido -NH protons were known lower than that of the thioureido -NH protons, the anion binding ability of urea-based receptor should have been lower than those thiourea-based. The observed opposite thus suggested that it was the stepwise allosteric interactions that afforded both high selectivity and sensitivity for F~-. The study was expected to be of help for the design and development of highly selective and sensitive anion receptors.
The main innovations of this dissertation were summarized and the prospection of the future work was discussed at the end.
第一章为前言。首先简要介绍了超分子化学的研究现状和发展趋势;然后评述分子识别研究中基于氢键作用的中性阴离子受体的发展近况,着重论述中性受体设计时面临的挑战和当前的应对策略;最后,以此为基础、并基于本实验室已有的研究积累,提出本论文的研究设想。
第二章为实验部分。详细介绍论文工作中所涉及主要试剂、仪器和受体分子的合成方法与结构鉴定。包括N-脂肪酰胺基-N'-(取代苯基)硫脲、聚-N-脂肪酰胺基-N'-苯基硫脲、N-乙酰胺基-N'-苯基脲、N-异烟酰胺基-N'-(取代苯基)硫脲和N-(2-(羟基)苄亚胺基)-N'-苯基脲等近三十种化合物。
第三章合成了一类具有良好阴离子识别性能的N-脂肪酰胺基-N'-(取代苯基)-硫脲类中性受体,运用吸收光谱法研究了其与阴离子的结合、作用模式和影响因素。发现N-酰胺基端为脂肪酰胺基时,硫脲-NH酸性降低,但受体与阴离子的结合常数却有所提高。醇效应实验和CD_3CN中的核磁滴定表明受体分子与阴离子间通过氢键作用维系。分子两端取代基对受体-阴离子的结合产生不同影响:N'-苯基端取代基的推拉电子能力影响受体与阴离子结合能力;N-酰胺基端取代基则影响受体-阴离子结合物的吸收光谱形状。玻片表面固载聚-N-酰胺基-N'-苯基硫脲受体,利用接触角研究了受体与阴离子间的相互作用。本章还提出了提高受体对阴离子结合选择性的两条新途径:一是受体具有适宜的结构时,适当降低硫脲-NH的酸性以减小受体对阴离子的结合能力,可改善受体对某种阴离子结合的选择性;二是运用分子印迹技术,提高受体与阴离子结合的选择性。
第四章合成了N-异烟酰胺基-N'-(取代苯基)硫脲类阴离子受体。受体分子以酰胺基硫脲为结合位点,吡啶环的引入可提高受体在水溶液中的溶解性。研究发现受体具有极强的阴离子结合性能,MeCN中与阴离子的结合常数大于10~7Lmol~(-1)数量级,可将阴离子识别拓展至H_2O-MeCN混合溶剂中。核磁滴定表明受体分子与阴离子间系氢键作用,无脱质子过程发生。首次实现了简单中性受体分子在纯水介质中的阴离子有效结合。基于酰胺-NH质子核磁位移的相关分析表明,分子中的吡啶环相当于含有强吸电子取代基的苯环,酰胺-NH质子足够的酸性,是受体具有良好阴离子结合性能的重要原因。但更为重要的因素在于极性溶液中分子两端的疏水芳基在疏水作用力下可相互靠近,形成一个有利于阴离子结合的疏水微环境,这是受体在水溶液仍保持较好的阴离子结合能力的关键因素。本研究为水溶液中中性阴离子受体的设计提供了一种新的策略,可望为基于硫脲基团的有机催化剂的设计提供借鉴。
第五章设计合成了一种新型的同源协同变构型荧光受体:N-(2-(羟基)苄亚胺基)-N'-苯基脲,对F~-表现出高的响应灵敏度和结合选择性:F~-导致受体MeCN溶液颜色由无色转变为黄色,荧光增强300余倍;CH_3CO_2~-和H_2PO_4~-等其它阴离子存在时溶液颜色均无此变化,荧光增强不足20倍。实验发现,分子中含有的两个阴离子结合位点,酚羟基-OH和两个脲基氮氢-NH,与F~-发生了分步反应:第一个F~-与受体酚羟基-OH结合,导致-OH脱质子,受体发生构型变化,增强了第二个F~-与受体脲基氮氢-NH的氢键结合。同时受体分子结构的柔性确保第一步反应对第二步反应产生的协同促进作用能顺利进行。而受体与CH_3CO_2~-和H_2PO_4~-等阴离子的氢键结合一步完成,脲基氮氢-NH的阴离子氢键结合能力较硫脲弱,因此受体与CH_3CO_2~-和H_2PO_4~-等的结合能力也较弱。可见分步结合和变构效应是受体对F~-具有强的结合能力和高选择性的关键。本实验为探索高灵敏和高选择性阴离子受体分子的设计作出了有益的尝试。
最后于附录部分总结了本论文的创新点,并展望后续研究工作。
Molecular recognition is one of the subjects receiving continuous interests in supramolecular chemistry. Since anions play a fundamental role in disclosing the essence of biological processes, anion recognition and sensing by synthetic receptors has received increasing recent attention. Especially, the development of neutral receptors based on hydrogen bonding has become a must for receptors of excellent anion-recognition ability. Selectivity and sensitivity are the key parameter in evaluating anion receptors, several strategies have been developed to improve anion-recognition ability of neutral receptors by incorporating more binding sites in a suitable arrangement, increasing the acidity of the hydrogen bonding donors, cooperating with electrostatic interactions, and utilizing allosteric interaction. In this thesis, a series of neutral anion receptors were designed and synthesized, employing the N-amido(thio)urea as an efficient binding site. Interactions of the binding moiety and anions were investigated in order to explore promising new approaches for improving anion-recognition ability of the neutral receptors.
The dissertation consists of five chapters summarized as the following.
Chapter 1 presents a general introduction to supramolecular chemistry relating to the researches in the development of neutral anion receptors based on hydrogen bond. Emphases were focused on the challenges existing in the design of neutral receptors, and the strategy resolving these problems. The objectives of this dissertation were proposed.
Chapter 2 describes the syntheses and characterization of ca. 30 receptors designed in this thesis for anion recognition, including N-aliphaticamido-N'-(substituted)phenyl (thio)urea, poly-(N-amido-N'-phenyl)thiourea, N-(isonicotinamido)-N'-(substitutedphenyl)thioureas, and N-(2-(hydroxyl)benzylimino)-N'-phenylurea. The equipments, materials and methods involved in this dissertation are also described.
Chapter 3 reports the anion binding of N-aliphaticamido-N-(substituted)phenyl (thio)urea. The N-amidothiourea binding site was employed on the basis of our previous work that showed a substantially enhanced anion binding affinity compared to the traditional N-phenylthiourea binding site. It was found that when the the acidity of thioureido -NH protons in N-aliphaticamido-N-phenylthioureas was lower than that in N-benzamido-N'-phenylthioureas, yet the anion binding ability was stronger. Protic solvent competition in MeCN by MeOH and ~1H NMR titrations in CD_CN supported the hydrogen bond interaction of the receptor with anion. The substituent of the N '-phenyl ring and of the N-amido group exist different influence on anion biding, the former remarkably influencing anion binding, while the latter affecting more to the absorption spectra of the receptor upon anion binding. Polymerizable N-amidothiourea-based receptors were polymerized and were fixated on the surface of glass. Contact angle measurements were used to understand interactions of anion and poly-N-amidothiourea-based receptors. Two new approaches were attempted to increase selectivity in anion binding, to properly decrease the acidity of thioureido -NH protons in a receptor with suitable structure, and to apply the molecular imprinting technology.
Chapter 4 presents the design of N-(isonicotinamido)-N'-(substituted-phenyl) thioureas as simple neutral anion receptors capable of binding anion in aqueous solutions. A pyridine terminal was chosen to improve water solubility of the receptor molecules. These receptors showed substantial anion-binding ability in MeCN solution with binding constants of 10~7 L mol~(-1) order of magnitude. Significantly is that they showed sensitive response to anions such as CH_3CO_2~- in aqueous solutions with binding constants of 10~3 L mol~(-1) order of magnitude. The hydrogen bonding interaction between the receptor and anion was proved by ~1H NMR titration in CD_3CN, with no deprotonation occurring. The pyridine ring was shown to correspond to a phenyl ring bearing an electron withdrawing para-substituent of Hammett constant 0.75, which implied that the amido -NH is acidic enough to afford the capability of anion binding in aqueous solutions. Although this seems to point to the critical role of the acidity of the amido -NH proton, we showed that it was instead the less polar hydrophobic microenvironment afforded by the approaching of two aromatic rings in these receptors driven by hydrophobic interaction that promoted the anion binding in aqueous solutions. A new approach was provided for designing neutral receptors based on hydrogen bonding for anion binding in aqueous solutions by taking into account the receptor molecular conformation.
Chapter 5 reports a homotropic allosteric receptor, N-(2-(hydroxyl)benzylimino)-N'-phenylurea, highly selective and sensitive for F~-. A moderate color change from colorless to yellow and a drastic fluorescence enhancement of c.a. 300 fold were observed when F~- is added to the receptor solution in MeCN, whereas other anion led to no color change and tiny fluorescence enhancement of less than 20 fold. The receptor bears three distinct hydrogen bonding groups, one phenolic -OH and two ureido NHs, which bind stepwise to F~-. Binding of the first F~- had a consequence of that of the subsequent interaction of the second F~-. The first F~- binding to the receptor's phenolic -OH resulted in the deprotonation and a conformation change in the receptor that reinforced its next binding to F~-. Differing from the stepwise binding to F~-, the receptor bound other anions such as CH_3CO_2~- and H_2PO_4~- in a single step via -OH and ureido -NH protons in a 1:1 stoichiometry. Since the acidity of the ureido -NH protons were known lower than that of the thioureido -NH protons, the anion binding ability of urea-based receptor should have been lower than those thiourea-based. The observed opposite thus suggested that it was the stepwise allosteric interactions that afforded both high selectivity and sensitivity for F~-. The study was expected to be of help for the design and development of highly selective and sensitive anion receptors.
The main innovations of this dissertation were summarized and the prospection of the future work was discussed at the end.
引文
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