基于离子自组装和环糊精包结作用的超分子聚集体的构建和表征
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摘要
超分子化学的研究对象是各种非共价相互作用的性质,以及通过这些非共价作用设计构建所得超分子材料的结构和功能。利用各种非共价键(如静电吸引、氢键、和主客体包结等)的作用规律对超分子体系进行适当调控,可以实现化学领域的分子信息学,包括在分子水平和超分子水平上的复制、传递、构建等过程中的信息存储。对超分子体系的研究有助于了解不同非共价键的作用规律,并进一步利用这些规律构建高度有序的功能超分子材料。本论文选取静电作用和主客体包结为主要驱动力,对以下超分子体系的结构和性质进行了详细的研究。
1、利用简便的离子自组装(ionic self-assembly, ISA)方法,通过复合对氨基偶氮苯盐酸盐(4-aminoazobenzene hydrochloride, AzoHCl)和脱氧胆酸钠(1-Adamantanamine hydro-chloride, NaDC),制备得到性质稳定的有机纳米棒。并利用1H NMR、POM、TEM、SEM、LCSM、DSC/TGA、XRD、UV-vis等表征手段对产物的结构和性质进行研究。复合物中AzoHCl和NaDC的化学计量比确认为1：2,构筑单元由一分子的AzoHCl和两分子的NaDC分别以静电力和氢键相互作用,说明在ISA中除静电作用外,其它非共价键也起重要作用。该有序聚集结构具有良好的结晶性,可以激发出荧光,在荧光共聚焦显微镜下可以观察到清晰的荧光图像。在激光光源激发下,获得了稳定的荧光光谱。通过简便的ISA方法引入带有一定功能基团的构筑单元,从而得到具有所需结构和性质的功能材料,这类设计对于功能性纳米材料的构建和应用具有一定的借鉴意义。
2、采用简便的ISA方法复合脱氧胆酸钠(sodium deoxycholate, NaDC)和1-金刚烷铵盐酸盐(1-Adamantanamine hydro-chloride, AdCl),制备得到有机单晶,通过单晶解析方法得到了ISA产物精确的分子排列信息。另外,利用环糊精包结的方法得到了三元热敏超分子体系。环糊精和金刚烷及其衍生物可以形成稳定的包结物,包结常数可达104-10’M-1。这种对温度敏感的焓驱动包结平衡为构建热敏超分子体系提供了可能,此处的实验结果证明了这种可能性。三元超分子体系可以在5℃下为澄清透明溶液,并稳定三个月以上；对该热敏体系加热至25℃或者更高温度,可通过破坏包结平衡进而破坏超分子的两亲性,析出不含环糊精的二元单晶。本研究利用ISA和环糊精包结两种非共价作用为主要驱动力,协同其他非共价作用,设计组装得到热敏超分子体系,对于构建外界刺激响应性超分子体系具有一定借鉴意义。另外,将盐效应引入ISA体系的单晶培养中的尝试,对单晶培养也有一定参考价值。
Supramolecular chemistry is the study on various non-covalent interactions (such as electrostatic attraction, hydrogen bonding arrays, host-guest inclusion, etc.) and the structures or functions of supramolecular materials fabricated by these non-covalent interactions. The chemistry of molecular information, including replication, transfer, and fabrication on molecular and supramolecular level, could be achieved through appropriate manipulation of the non-covalent interactions. The research of supramolecular systems is helpful to learn about their mechanism and further to construct highly ordered functional materials. The present thesis is related to the design and assembly of supramolecular aggregates using ionic attraction and cyclodextrins inclusion as main driving forces, and the following assembly systems were studied in detail.
1. Through a facile ionic self-assembly (ISA), the organic nanosticks by complexing of 4-aminoazobenzene hydrochloride (AzoHCl) and 1-Adamantanamine hydro-chloride (NaDC) have been synthesized. The properties and structures of the nanosticks are characterized respectively by various techniques including 1H NMR, POM, TEM, SEM, LCSM, DSC/TGA, XRD, and UV-visible spectroscopy. The stoichiometry between AzoHCl and NaDC in the complexes is determined as a 1:2 molar ratio. The basic building block is composed of one AzoHCl combined with two NaDC by electrostatic interaction and hydrogen bond respectively, which proves that electrostatic interaction is not the only main driving force in ISA, and other interactions such as H-bonding may also be important driving force cooperated with electrostatic interaction. The nanosticks with well crystalline and fluorescent feature could be observed via a laser con-focal scanning microscopy (LCSM). Various functional supramolecular materials could be produced via such a facial ISA strategy using small organic molecules with functional groups.
2. The ionic self-assembled organic single-crystals are obtained through complexing two functional molecules, sodium deoxycholate (NaDC) and 1-Adamantanamine hydro-chloride (AdCl), and the exact molecular arrangement of ISA product is obtained from single-crystal analysis. Meanwhile, the amphiphilicity of the complex could be changed by a supramolecular approach using cyclodextin (CD) inclusion, and a thermo-sensitive system is therefore obtained. The high association constants between Ad derivatives andβ-CD (β-cyclodextin) have been reported on the order of 104-105 M"1. The enthalpy-driven and temperature dependent association equilibrium makes it possible for CD inclusions to be thermo-sensitive. The obtained results here have confirmed the expectation thatβ-CD could include Ad blocks and form thermo-sensitive supramolecular inclusions. This three-component superamolecular solution is stable and keeps transparency for more than three months at 5℃. When the temperature was increased from 5 to 25℃or higher, the molecular amphiphilicity is changed via inclusion equilibrium shifting, and another two-component microrods were observed appearing from this three-component solution. Thermo-sensitive supermolecular system is obtained via the cooperation of ISA, cyclodextrin inclusion and other non-covalent interactions, which indicates that various external-stimuli responsive materials could be fabricated based on these non-covalent interactions. In addition, the observed salt effect could be considered in the process of single crystal growth for other ISA systems.
Thanks for the supports from the National Natural Science Foundation of China (No.20773080 and 20973104).
1、利用简便的离子自组装(ionic self-assembly, ISA)方法,通过复合对氨基偶氮苯盐酸盐(4-aminoazobenzene hydrochloride, AzoHCl)和脱氧胆酸钠(1-Adamantanamine hydro-chloride, NaDC),制备得到性质稳定的有机纳米棒。并利用1H NMR、POM、TEM、SEM、LCSM、DSC/TGA、XRD、UV-vis等表征手段对产物的结构和性质进行研究。复合物中AzoHCl和NaDC的化学计量比确认为1：2,构筑单元由一分子的AzoHCl和两分子的NaDC分别以静电力和氢键相互作用,说明在ISA中除静电作用外,其它非共价键也起重要作用。该有序聚集结构具有良好的结晶性,可以激发出荧光,在荧光共聚焦显微镜下可以观察到清晰的荧光图像。在激光光源激发下,获得了稳定的荧光光谱。通过简便的ISA方法引入带有一定功能基团的构筑单元,从而得到具有所需结构和性质的功能材料,这类设计对于功能性纳米材料的构建和应用具有一定的借鉴意义。
2、采用简便的ISA方法复合脱氧胆酸钠(sodium deoxycholate, NaDC)和1-金刚烷铵盐酸盐(1-Adamantanamine hydro-chloride, AdCl),制备得到有机单晶,通过单晶解析方法得到了ISA产物精确的分子排列信息。另外,利用环糊精包结的方法得到了三元热敏超分子体系。环糊精和金刚烷及其衍生物可以形成稳定的包结物,包结常数可达104-10’M-1。这种对温度敏感的焓驱动包结平衡为构建热敏超分子体系提供了可能,此处的实验结果证明了这种可能性。三元超分子体系可以在5℃下为澄清透明溶液,并稳定三个月以上；对该热敏体系加热至25℃或者更高温度,可通过破坏包结平衡进而破坏超分子的两亲性,析出不含环糊精的二元单晶。本研究利用ISA和环糊精包结两种非共价作用为主要驱动力,协同其他非共价作用,设计组装得到热敏超分子体系,对于构建外界刺激响应性超分子体系具有一定借鉴意义。另外,将盐效应引入ISA体系的单晶培养中的尝试,对单晶培养也有一定参考价值。
Supramolecular chemistry is the study on various non-covalent interactions (such as electrostatic attraction, hydrogen bonding arrays, host-guest inclusion, etc.) and the structures or functions of supramolecular materials fabricated by these non-covalent interactions. The chemistry of molecular information, including replication, transfer, and fabrication on molecular and supramolecular level, could be achieved through appropriate manipulation of the non-covalent interactions. The research of supramolecular systems is helpful to learn about their mechanism and further to construct highly ordered functional materials. The present thesis is related to the design and assembly of supramolecular aggregates using ionic attraction and cyclodextrins inclusion as main driving forces, and the following assembly systems were studied in detail.
1. Through a facile ionic self-assembly (ISA), the organic nanosticks by complexing of 4-aminoazobenzene hydrochloride (AzoHCl) and 1-Adamantanamine hydro-chloride (NaDC) have been synthesized. The properties and structures of the nanosticks are characterized respectively by various techniques including 1H NMR, POM, TEM, SEM, LCSM, DSC/TGA, XRD, and UV-visible spectroscopy. The stoichiometry between AzoHCl and NaDC in the complexes is determined as a 1:2 molar ratio. The basic building block is composed of one AzoHCl combined with two NaDC by electrostatic interaction and hydrogen bond respectively, which proves that electrostatic interaction is not the only main driving force in ISA, and other interactions such as H-bonding may also be important driving force cooperated with electrostatic interaction. The nanosticks with well crystalline and fluorescent feature could be observed via a laser con-focal scanning microscopy (LCSM). Various functional supramolecular materials could be produced via such a facial ISA strategy using small organic molecules with functional groups.
2. The ionic self-assembled organic single-crystals are obtained through complexing two functional molecules, sodium deoxycholate (NaDC) and 1-Adamantanamine hydro-chloride (AdCl), and the exact molecular arrangement of ISA product is obtained from single-crystal analysis. Meanwhile, the amphiphilicity of the complex could be changed by a supramolecular approach using cyclodextin (CD) inclusion, and a thermo-sensitive system is therefore obtained. The high association constants between Ad derivatives andβ-CD (β-cyclodextin) have been reported on the order of 104-105 M"1. The enthalpy-driven and temperature dependent association equilibrium makes it possible for CD inclusions to be thermo-sensitive. The obtained results here have confirmed the expectation thatβ-CD could include Ad blocks and form thermo-sensitive supramolecular inclusions. This three-component superamolecular solution is stable and keeps transparency for more than three months at 5℃. When the temperature was increased from 5 to 25℃or higher, the molecular amphiphilicity is changed via inclusion equilibrium shifting, and another two-component microrods were observed appearing from this three-component solution. Thermo-sensitive supermolecular system is obtained via the cooperation of ISA, cyclodextrin inclusion and other non-covalent interactions, which indicates that various external-stimuli responsive materials could be fabricated based on these non-covalent interactions. In addition, the observed salt effect could be considered in the process of single crystal growth for other ISA systems.
Thanks for the supports from the National Natural Science Foundation of China (No.20773080 and 20973104).
引文
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