几种环糊精和杯芳烃衍生物的合成及其组装体的功能研究
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摘要
超分子化学是近年来的研究热点,其中环糊精和杯芳烃作为第二、三代主体化合物广泛的应用在分子识别和组装过程中。本文合成了苝酰亚胺桥联全甲基化-β-环糊精衍生物、萘酰亚胺和苯酰亚胺桥联全甲基化-β-环糊精衍生物以及杯芳烃的衍生物,研究了其在自组装、客体识别和光诱导电子转移方面的应用。其内容主要分为以下部分:
1.简要介绍了基于环糊精构筑的光诱导电子转移体系的最新进展,酰亚胺类衍生物与卟啉类构筑的电子转移体系,苝酰亚胺的自组装行为以及杯芳烃在荧光传感方面的应用。
2.合成了一系列新型的环糊精和杯芳烃衍生物,其中包括两个苝酰亚胺桥联全甲基化-β-环糊精衍生物,两个萘酰亚胺和苯酰亚胺桥联全甲基化-β-环糊精衍生物,二茂铁和氨甲基芘修饰的全甲基化-β-环糊精衍生物,以及2个杯[4]芳烃桥联全甲基化-β-环糊精衍生物和5个杯芳烃衍生物。化合物的结构经核磁、质谱、红外和元素分析鉴定。
3.通过π…π堆积作用构筑了基于苝酰亚胺桥联全甲基化-β-环糊精衍生物(CD-1)的一维纳米超分子组装体。紫外光谱、荧光光谱和~1H NMR研究了CD-1在不同溶剂中的π…π堆积行为,表明CD-1在水溶液中有较强的堆积能力。浓度相关和温度相关的紫外光谱研究了CD-1的自组装过程,浓度增加有利于组装体的形成,温度升高使之解聚。TEM和SEM研究表明组装体形成规则有序的一维纳米棒状结构,在偏光显微镜下表现了一定的光学性质,荧光显微镜下显示红色的固态荧光,X—射线粉末衍射得到了相邻苝酰亚胺之间的π…π距离为4.02(?)。进而将CD-1负载到聚偏氟乙烯膜上研究了对有机挥发性气体的固态荧光传感,在低浓度下表现了对胺类的高灵敏度的识别作用。
4.通过紫外光谱、荧光光谱和~-H NMR研究了苝酰亚胺桥联全甲基化-乙二胺-β-环糊精衍生物(CD-2)在不同溶剂中的π…π堆积行为,表明CD-2在水溶液中有较强的堆积能力。浓度相关和温度相关紫外光谱分别研究了CD-2质子化前后的堆积能力,表明质子化前CD-2具有较强的π…π堆积能力。荧光光谱研究了CD-2质子化前后的荧光性质,表明质子化后CD-2由于分子内电子转移阻断和弱的堆积能力而显示了强的荧光。进而,我们研究了CD-2对水溶性芳香类客体分子的识别作用,利用客体分子与苝酰亚胺之间的电子相互作用以及环糊精对客体分子的包结作用引起的苝酰亚胺聚集行为的改变,实现了对2-蒽酸钠和芘丁酸钠的选择性传感。
5.通过萘酰亚胺和苯酰亚胺桥联全甲基化-β-环糊精衍生物(CD-3和CD-4)与水溶性卟啉和锌卟啉构筑了超分子线状组装体。用紫外光谱研究了CD-3和CD-4与水溶性卟啉和锌卟啉的络合过程,主客体分子之间形成稳定的n:n型的络合物。AFM和TEM研究表明主客体分子间形成了规则有序的超分子纳米线状组装体,并且通过凝胶渗透色谱测定得到了超分子组装体的平均分子量。进而通过荧光光谱和荧光寿命研究了组装体中的光诱导电子转移过程,CD-3与水溶性卟啉和锌卟啉间存在明显的光诱导电子转移过程,而CD-4与水溶性卟啉和锌卟啉之间不能发生。通过电化学分析、重组能计算和圆二色光谱分析了CD-4与卟啉间不能发生电子转移的可能的原因。
6.通过紫外光谱和荧光光谱研究了CD-1与锌卟啉的络合过程。当激发卟啉时络合物中存在电子转移过程,而激发苝酰亚胺时则是能量转移过程,实现了波长依赖的电子转移和能量转移的可调控的过程,并且通过紫外光谱和圆二色光谱研究了主客体分子间不同寻常的不同荧光基团之间存在的强的激子耦合现象。
7.通过荧光光谱研究了上沿两个氨甲基芘基修饰,下沿四个乙酯基修饰的杯[4]芳烃衍生物对碱金属和碱土金属的荧光传感。主体化合物对钠离子表现了较高的选择性,荧光滴定光谱研究表明其稳定常数为2190 mol~(-1)·L。氨甲基芘作为荧光探针,四个乙酯基作为离子的键合位点,利用芘基的“excimer”峰和“monomer”峰对空间距离的敏感响应实现了钠离子诱导构型改变的荧光传感。
Supramolecular chemistry is an important research field in current chemistry. Cyclodextrin and Calixarene derivatives as the first generation and second generation host compounds have been widely applied in the molecular recognition and construction of supramolecular assembly.In this thesis,perylene bisimide-bridged bis-(permethyl-β-cyclodextrins),perylene bisimide-bridged bis-(permethyl-ethylenediamino-β-cyclodextrins), naphthalene diimide and pyromellitimide bridged permethyl-β-cyclodextrin,and a series of calixarene derivatives were synthesized. Furthermore,their assembly behaviors,molecular recognition and photoinduced electron transfer process in the supramolecular assembly were investigated.The major contents of this thesis are as follows:
1.The new progress and important achievement of photoinduced electron transfer based on cyclodextrin,the photoinduced electron transfer process between imide derivatives and porphyrin,the self-assembly behavior of perylene bisimides and the fluorescence sensor based on calixarene were described briefly.
2.A series of cyclodextrin and calixarene derivatives were synthesized, including:two perylene bisimide-bridged bis-(permethyl-β-cyclodextrins),two naphthalene diimide and pyromellitimide bridged permethyl-β-cyclodextrin,two ferrocence and pyrene modified permethyl-β-cyclodextrins,two calix arene-briged permethyl-β-cyclodextrin and five calixarene derivatives.These structures were proved by NMR,MS,IR and elemental analysis.
3.One nanoscopic supramolecular aggregate was constructed from perylene bisimide-bridged bis-(permethyl-β-cyclodextrins) CD-1 viaπ…πstacking interactions.Its self-assembly behaviors in organic and aqueous solutions were investigated by UV-Vis,fluorescence and ~1H NMR spectroscopies.The TEM and SEM images show the one-dimensional nanorod aggregation of CD-1,which is birefringent under crossed polarizer conditions,and strongly fluorescent as depicted in the fluorescence microscopy image.X-ray powder diffraction measurement indicates that CD-1 forms a well-ordered crystalline arrangement withπ…πstacking distance of 4.02(?).Furthermore,the solid-state fluorescent sensing was explored by utilizing the poly(vinylidene fluoride) membrane-embedded CD-1,giving that CD-1, as one novel vapor detecting material,can probe several kinds of volatile organic compounds,and especially,exhibits high sensitivity to organic amines.
4.Theπ…πstacking behavior of perylene bisimide-bridged bis-(permethyl-ethylenediamino-β-cyclodextrins) (CD-2) was investigated by UV-Vis,fluorescence and ~1H NMR spectra,showing that CD-2 exhibited strongπ…πstacking interaction in water.Especially,the aggregation and optical properties were comprehensively compared between the neutral form and protonated form of CD-2 through the concentration-dependent and temperature-dependent UV-Vis experiments.The aggregation constant of CD-2 at the protonated form is almost one order of magnitude lower than that of CD-2 at the neutral form owing to the electrostatic repulsion among CD-2 themselves.On the other hand,CD-2 at the protonated form exhibits better fluorescence than the neutral form by overcoming the photoinduced electron-transfer process from imino groups to perylene backbones.Furtherfore,four water-soluble aromatic guests were used to investigated the complexing interactions with CD-2.Because of the electron interactions between the host and guests and the changes of the aggregation behavior induced by the complex of the guests,the absorbance of CD-2 was obvious red shift,which displaied sensing for 2-anthracene acid sodium and pyrene-butyl acid sodium.
5.A series of supramolecular wirelike assemblies were constructed by the naphthalene diimide and pyromellitimide bridged permethyl-β-cyclodextrins upon complexation with water-soluble(metal) porphyrins,which were comprehensively characterized by UV-Vis spectroscopy,NMR,atomic force microscopy,scanning electron microscopy,and gel permeation chromatography.Fluorescence and electrochemical measurements demonstrated that the effective electron-transfer processes were observed in the regular arrays of multiple donors and acceptors formed by naphthalene diimide bridged permethyl-β-cyclodextrin and porphyrins, while did not for the case of pyromellitimide bridged permethyl-β-cyclodextrin. Moreover,the electron-transfer efficiencies mainly rely on the distinguishable excited energies of porphyrin and metal porphyrin.And the possible reasons were investigated by electrochemistry analysis,reorganization energy analysis and circular dichroism spectrum.
6.Supramolecular complex was constructed by perylene bisimide-bridged bis-(permethyl-β-cyclodextrins) CD-1 upon complexation with water-soluble porphyrin,which were comprehensively characterized by UV-Vis spectroscopy.The photophysical hebavior of the supramolecular complex was investigated by fluorescence spectrum and fluorescence lifetime.The observed behavior sharply changes with excitation wavelength,depending on whether the porphyrin or the perylene bisimides units are excitation.After porphyrin excitation,the fluorescence typical of this unit is quenched about 80%,because of the photoinduced electron transfer from porphyrin to perylene bisimides.Upon excitation of the perylene bisimides fragment,the fluorescence was quenched due to the energy transfer process from perylene bisimides to porphyrin.And the strong exciton coupling interactions between perylene bisimides and porphyrin were studied by UV-Vis and circular dichroism spectrum.
7.The chemosensing behaviors of host compound for alkali and alkaline earth metal ions were investigated by fluorescence spectroscopy.The obtained results show that the calixarene host can selectively bind sodium ion with the complexation stability constant of 2190 mol~(-1)·L.The complexation with sodium ion can pronouncedly induce the excimer emission decreased and the monomer emission increased,whereas the addition of the other alkali and alkaline earth metal ions does not cause appreciable changes in the fluorescence spectrum of the host compound.
1.简要介绍了基于环糊精构筑的光诱导电子转移体系的最新进展,酰亚胺类衍生物与卟啉类构筑的电子转移体系,苝酰亚胺的自组装行为以及杯芳烃在荧光传感方面的应用。
2.合成了一系列新型的环糊精和杯芳烃衍生物,其中包括两个苝酰亚胺桥联全甲基化-β-环糊精衍生物,两个萘酰亚胺和苯酰亚胺桥联全甲基化-β-环糊精衍生物,二茂铁和氨甲基芘修饰的全甲基化-β-环糊精衍生物,以及2个杯[4]芳烃桥联全甲基化-β-环糊精衍生物和5个杯芳烃衍生物。化合物的结构经核磁、质谱、红外和元素分析鉴定。
3.通过π…π堆积作用构筑了基于苝酰亚胺桥联全甲基化-β-环糊精衍生物(CD-1)的一维纳米超分子组装体。紫外光谱、荧光光谱和~1H NMR研究了CD-1在不同溶剂中的π…π堆积行为,表明CD-1在水溶液中有较强的堆积能力。浓度相关和温度相关的紫外光谱研究了CD-1的自组装过程,浓度增加有利于组装体的形成,温度升高使之解聚。TEM和SEM研究表明组装体形成规则有序的一维纳米棒状结构,在偏光显微镜下表现了一定的光学性质,荧光显微镜下显示红色的固态荧光,X—射线粉末衍射得到了相邻苝酰亚胺之间的π…π距离为4.02(?)。进而将CD-1负载到聚偏氟乙烯膜上研究了对有机挥发性气体的固态荧光传感,在低浓度下表现了对胺类的高灵敏度的识别作用。
4.通过紫外光谱、荧光光谱和~-H NMR研究了苝酰亚胺桥联全甲基化-乙二胺-β-环糊精衍生物(CD-2)在不同溶剂中的π…π堆积行为,表明CD-2在水溶液中有较强的堆积能力。浓度相关和温度相关紫外光谱分别研究了CD-2质子化前后的堆积能力,表明质子化前CD-2具有较强的π…π堆积能力。荧光光谱研究了CD-2质子化前后的荧光性质,表明质子化后CD-2由于分子内电子转移阻断和弱的堆积能力而显示了强的荧光。进而,我们研究了CD-2对水溶性芳香类客体分子的识别作用,利用客体分子与苝酰亚胺之间的电子相互作用以及环糊精对客体分子的包结作用引起的苝酰亚胺聚集行为的改变,实现了对2-蒽酸钠和芘丁酸钠的选择性传感。
5.通过萘酰亚胺和苯酰亚胺桥联全甲基化-β-环糊精衍生物(CD-3和CD-4)与水溶性卟啉和锌卟啉构筑了超分子线状组装体。用紫外光谱研究了CD-3和CD-4与水溶性卟啉和锌卟啉的络合过程,主客体分子之间形成稳定的n:n型的络合物。AFM和TEM研究表明主客体分子间形成了规则有序的超分子纳米线状组装体,并且通过凝胶渗透色谱测定得到了超分子组装体的平均分子量。进而通过荧光光谱和荧光寿命研究了组装体中的光诱导电子转移过程,CD-3与水溶性卟啉和锌卟啉间存在明显的光诱导电子转移过程,而CD-4与水溶性卟啉和锌卟啉之间不能发生。通过电化学分析、重组能计算和圆二色光谱分析了CD-4与卟啉间不能发生电子转移的可能的原因。
6.通过紫外光谱和荧光光谱研究了CD-1与锌卟啉的络合过程。当激发卟啉时络合物中存在电子转移过程,而激发苝酰亚胺时则是能量转移过程,实现了波长依赖的电子转移和能量转移的可调控的过程,并且通过紫外光谱和圆二色光谱研究了主客体分子间不同寻常的不同荧光基团之间存在的强的激子耦合现象。
7.通过荧光光谱研究了上沿两个氨甲基芘基修饰,下沿四个乙酯基修饰的杯[4]芳烃衍生物对碱金属和碱土金属的荧光传感。主体化合物对钠离子表现了较高的选择性,荧光滴定光谱研究表明其稳定常数为2190 mol~(-1)·L。氨甲基芘作为荧光探针,四个乙酯基作为离子的键合位点,利用芘基的“excimer”峰和“monomer”峰对空间距离的敏感响应实现了钠离子诱导构型改变的荧光传感。
Supramolecular chemistry is an important research field in current chemistry. Cyclodextrin and Calixarene derivatives as the first generation and second generation host compounds have been widely applied in the molecular recognition and construction of supramolecular assembly.In this thesis,perylene bisimide-bridged bis-(permethyl-β-cyclodextrins),perylene bisimide-bridged bis-(permethyl-ethylenediamino-β-cyclodextrins), naphthalene diimide and pyromellitimide bridged permethyl-β-cyclodextrin,and a series of calixarene derivatives were synthesized. Furthermore,their assembly behaviors,molecular recognition and photoinduced electron transfer process in the supramolecular assembly were investigated.The major contents of this thesis are as follows:
1.The new progress and important achievement of photoinduced electron transfer based on cyclodextrin,the photoinduced electron transfer process between imide derivatives and porphyrin,the self-assembly behavior of perylene bisimides and the fluorescence sensor based on calixarene were described briefly.
2.A series of cyclodextrin and calixarene derivatives were synthesized, including:two perylene bisimide-bridged bis-(permethyl-β-cyclodextrins),two naphthalene diimide and pyromellitimide bridged permethyl-β-cyclodextrin,two ferrocence and pyrene modified permethyl-β-cyclodextrins,two calix arene-briged permethyl-β-cyclodextrin and five calixarene derivatives.These structures were proved by NMR,MS,IR and elemental analysis.
3.One nanoscopic supramolecular aggregate was constructed from perylene bisimide-bridged bis-(permethyl-β-cyclodextrins) CD-1 viaπ…πstacking interactions.Its self-assembly behaviors in organic and aqueous solutions were investigated by UV-Vis,fluorescence and ~1H NMR spectroscopies.The TEM and SEM images show the one-dimensional nanorod aggregation of CD-1,which is birefringent under crossed polarizer conditions,and strongly fluorescent as depicted in the fluorescence microscopy image.X-ray powder diffraction measurement indicates that CD-1 forms a well-ordered crystalline arrangement withπ…πstacking distance of 4.02(?).Furthermore,the solid-state fluorescent sensing was explored by utilizing the poly(vinylidene fluoride) membrane-embedded CD-1,giving that CD-1, as one novel vapor detecting material,can probe several kinds of volatile organic compounds,and especially,exhibits high sensitivity to organic amines.
4.Theπ…πstacking behavior of perylene bisimide-bridged bis-(permethyl-ethylenediamino-β-cyclodextrins) (CD-2) was investigated by UV-Vis,fluorescence and ~1H NMR spectra,showing that CD-2 exhibited strongπ…πstacking interaction in water.Especially,the aggregation and optical properties were comprehensively compared between the neutral form and protonated form of CD-2 through the concentration-dependent and temperature-dependent UV-Vis experiments.The aggregation constant of CD-2 at the protonated form is almost one order of magnitude lower than that of CD-2 at the neutral form owing to the electrostatic repulsion among CD-2 themselves.On the other hand,CD-2 at the protonated form exhibits better fluorescence than the neutral form by overcoming the photoinduced electron-transfer process from imino groups to perylene backbones.Furtherfore,four water-soluble aromatic guests were used to investigated the complexing interactions with CD-2.Because of the electron interactions between the host and guests and the changes of the aggregation behavior induced by the complex of the guests,the absorbance of CD-2 was obvious red shift,which displaied sensing for 2-anthracene acid sodium and pyrene-butyl acid sodium.
5.A series of supramolecular wirelike assemblies were constructed by the naphthalene diimide and pyromellitimide bridged permethyl-β-cyclodextrins upon complexation with water-soluble(metal) porphyrins,which were comprehensively characterized by UV-Vis spectroscopy,NMR,atomic force microscopy,scanning electron microscopy,and gel permeation chromatography.Fluorescence and electrochemical measurements demonstrated that the effective electron-transfer processes were observed in the regular arrays of multiple donors and acceptors formed by naphthalene diimide bridged permethyl-β-cyclodextrin and porphyrins, while did not for the case of pyromellitimide bridged permethyl-β-cyclodextrin. Moreover,the electron-transfer efficiencies mainly rely on the distinguishable excited energies of porphyrin and metal porphyrin.And the possible reasons were investigated by electrochemistry analysis,reorganization energy analysis and circular dichroism spectrum.
6.Supramolecular complex was constructed by perylene bisimide-bridged bis-(permethyl-β-cyclodextrins) CD-1 upon complexation with water-soluble porphyrin,which were comprehensively characterized by UV-Vis spectroscopy.The photophysical hebavior of the supramolecular complex was investigated by fluorescence spectrum and fluorescence lifetime.The observed behavior sharply changes with excitation wavelength,depending on whether the porphyrin or the perylene bisimides units are excitation.After porphyrin excitation,the fluorescence typical of this unit is quenched about 80%,because of the photoinduced electron transfer from porphyrin to perylene bisimides.Upon excitation of the perylene bisimides fragment,the fluorescence was quenched due to the energy transfer process from perylene bisimides to porphyrin.And the strong exciton coupling interactions between perylene bisimides and porphyrin were studied by UV-Vis and circular dichroism spectrum.
7.The chemosensing behaviors of host compound for alkali and alkaline earth metal ions were investigated by fluorescence spectroscopy.The obtained results show that the calixarene host can selectively bind sodium ion with the complexation stability constant of 2190 mol~(-1)·L.The complexation with sodium ion can pronouncedly induce the excimer emission decreased and the monomer emission increased,whereas the addition of the other alkali and alkaline earth metal ions does not cause appreciable changes in the fluorescence spectrum of the host compound.
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