喹吖啶酮及芳香胺化合物：自组装、发光及堆积结构的研究
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摘要
本文设计、合成了四种氟原子取代喹吖啶酮衍生物、四种三氟甲基取代喹吖啶酮衍生物、两种三氟甲基取代芳香胺化合物(三氟甲基喹吖啶酮的中间体氧化产物),研究了含氟原子喹吖啶酮化合物的自组装特性、四甲基喹吖啶酮化合物的扭曲自组装行为及芳香胺化合物的热诱导固态发光开关性质,探讨了有机固体发光材料堆积结构与自组装及固态发光性能的关系。
1、合成了不同长度烷基取代的氟代喹吖啶酮(Cn-DFQA)和三氟甲基喹吖啶酮(Cn-DTFMQA)衍生物,并通过氧化喹吖啶酮中间体的方法分别获得了双三氟甲基取代(AA-1)和四个三氟甲基取代(AA-2)的芳香胺化合物。对化合物组成与结构进行了确认,考察了化合物的溶液光物理性质,获得了九种单晶。
2、以Cn-DFQA和Cn-DTFMQA化合物为构筑基元进行自组装微米材料研究。Cn-DFQA微米材料的形貌和性质明显具有烷基链长度依赖特性。单晶结构分析表明,C4-DFQA与C8-DFQA分子均通过π…π相互作用形成一维分子柱,而C10-DFQA与C16-DFQA的分子堆积结构和弱相互作用都十分类似,分子通过弱相互作用形成分子层。以C8-DTFMQA和C12-DTFMQA制备了长度超过1mm的超长微米材料,单晶研究表明分子的一维组装优势是制备超长微米材料的主要原因之一。
3、以非手性中心对称的C6-TMQA和C10-TMQA化合物为构筑基元,通过掺杂某些特定溶剂(乙醇、正丙醇、异丙醇、乙酸和丙酸)成功制备了具有扭曲形貌的自组装纤维,扭曲纤维具有热致变色性质。运用光谱、单晶及分子模拟等手段,我们提出了该系列化合物扭曲的可能起因:在掺杂溶剂存在下,喹吖啶酮分子在组装时会发生交错式的堆积导致最终扭曲结构的形成。
4、研究了三氟甲基取代芳香胺衍生物(AA-1与AA-2)的固态发光开关行为,两种化合物均具有热诱导可逆固态相转变特性并伴随发光颜色的变化。通过控制熔融样品的冷却速度可以获得不同的发光相态,此外,还观察到了两个“单晶-单晶”转变过程。通过对比单晶结构与实验现象,我们认为分子堆积结构的相互转换是获得固态发光开关的原因。我们还发现了其中一种AA-2绿色晶体具有固体蓝移发射特性,通过分子模拟我们认为在该绿色单晶中分子几何结构的较大变形导致能级差显著升高是导致该固体发射蓝移的主要原因。
Organic semiconductor materials, possessing several notable advantages including easy design and synthesis, mechanical flexibility, and low cost, have been used as active elements in optoelectronic devices such as organic light emitting diodes (OLEDs), solar cells, sensors, field effect transistors, optical waveguides and lasers. Recently, molecular materials fabricated from organic molecules through non-covalent interactions (hydrogen bondings,π-πinteractions, metal-metal interactions, etc.), have gradually become a research hotspot. Organic molecules can be prepared into molecular materials (micro-/nano-materials, thin films, single crystals, etc.) with abundant functions such as electricity, light, sensor, energy conversion, molecular machines etc, because of intermolecular non-covalent interaction. For organic solid materials, the constituent molecules may form strong intermolecular interactions and assembly packing structures resulting in that the properties of these materials are governed by the whole collective rather than by individual molecules. The performance of organic molecule-based devices strongly depends on the molecular assembly structures. Therefore, understanding and controlling molecular arrangement in solid state are fundamental issues for obtaining the solid material with desired chemical and physical properties.
1. In chapter II, four fluorinated quinacridone compounds (Cn-DFQA, n = 4, 8, 10, 16), four quinacridone derivatives substituted with trifiuoromethyl (Cn-DTFMQA, n = 4, 8, 12, 16) and two trifluoromethyl substituted aromatic amine compounds (AA-1 and AA-2) have been synthesized. All the compounds are obtained in high yields and characterized by ~1H NMR spectroscopy, mass spectra, and element analysis. The concentration-dependent photophysics properties (absorption spectra, emission spectra and the Photoluminescence quantum efficiency) of synthesized compounds in solutions have been studied in detail.
2. In chapter III, it was demonstrated that Cn-DFQA could be used as building blocks to fabricate organic luminescent micro-materials. The assembly properties of Cn-DFQA have obvious alky chain length dependent characteristic. The alky chain length has dramatic effect on the morphology of the resulted micro-materials. The molecules C4-DFQA and C8-DFQA with shorter alky chains could assemble into 1-D micro-materials, while C10-DFQA and C16-DFQA with longer alky chains aggregate into diamond and hexagonal micro-particle crystals, respectively. The emission spectra of the 1-D micro-materials formed by C4-DFQA or C8-DFQA exhibited red shift compared with that of the micro-particle crystals composed of C10-DFQA or C16-DFQA. The single crystal structure analysis revealed that in the crystals C4-DFQA and C8-DFQA there are 1-D molecular columns based on intermolecularπ…πand hydrogen bond interactions, while 2-D hydrogen bond molecular sheets are observed in the crystals C10-DFQA and C16-DFQA. The molecular packing properties of the four crystals suggest that C4-DFQA and C8-DFQA molecules have the tendency to form 1-D structure, while C10-DFQA and C16-DFQA molecules posses the characteristic to generate the sheet structures. The single crystal structures give a rational explanation for the alky chain length dependent morphology properties of the Cn-DFQA based micro materials. Therefore, it is possible to control the morphologies and emission properties of the organic micro and nano-materials through varying the molecular structures.
Self-assembled 1D nanostructures with distinct morphologies are fabricated by the deposition of Cn-DTFMQA solutions (1.0×10~(-3)M). The microstructures fabricated from C8-DTFMQA and C12-DTFMQA give ultralong 1D nanowires (more than 1 mm) with high aspect ratios. The investigation of the crystal structure suggests that DTFMQA-C8 molecules should have the tendency to aggregate into a straight liner 1-D structure in nature. The single crystal structure feature of C8-DTFMQA provided a rational explanation for the formation of the flat fibers. It is known that the energy of hydrogen bong is C=O…H-C >π…π> C-F…H-C, so the 1D aggregate tendency of C8-DTFMQA molecules is the kay factor to form ultralong micromaterials.
3. In chapter IV, we show that two achiral center-symmetrical quinacridone (QA) derivatives, N,N'-di(n-hexyl)-1,3,8,10-tetramethylquinacridone (C6TMQA) and N,N'-di(n-decyl)-1,3,8,10-tetramethylquinacridone (C10TMQA), could be employed as building blocks to fabricate well-defined twisted nanostructures by controlling the mixture solvent's composition and concentration. The bowknot-like bundles with twisted fiber arms were prepared based on C6TMQA. The uniform twisted fibers were generated from C10TMQA in ethanol/THF solution. The scanning electron microscope (SEM), UV-Vis spectra, differential scanning Calorimetry (DSC), X-ray diffraction, infrared (IR), nuclear magnetic resonance (NMR), single crystal and molecule simulations characterizations revealed that the introduction of ethanol molecules in the solution systems could induce the staggered aggregation of C6-TMQA (or C10-TMQA) molecules and the formation of twisted nanostructures. The twisted materials generated from achiral organic functional molecules may be valuable to the design and fabrication of new materials for optoelectronic applications. The twisted materials generated from achiral organic functional molecules may be valuable to the design and fabrication of new materials for optoelectronic applications.
4. In chapter V, AA-1 and AA-2 display thermo-induced and revisable solid sate phase transformation properties, which are accompanied by the switches between the different emission colors. For AA-1 or AA-2, the different phases could be obtained by controlling the solidification speed of the melted AA-1 or AA-2 sample. The red phases of AA-1 and AA-2 can undergo solid phase transfer into corresponding yellow phase of AA-1 and green AA-2 phase, respectively. The single crystal to single crystal transformation from red crystal AA-1 to yellow crystal AA-1 has been achieved. The phase dependent emission properties of AA-1 and AA-2 have been attributed to the different molecular packing properties and changeable molecular geometry for different solid phases of AA-1 and AA-2. The novel organic luminescence materials AA-1 and AA-2, which could be efficiently switched between two different luminescent phases based on the external thermal stimulation, may be employed to fabricate the display, sensing, memory devices.
In summary, we have synthesized and characterized ten novel organic light-emitting materials. Their concentration-dependent photophysical properties in solution were investigated, and nine single crystals were grown and their structures were analyzed. Through investigating the self-assembly behaviors of Cn-DFQA, Cn-DTFMQA and Cn-TMQA and the thermal induced solid-state luminescent switch behaviors of AA-1 and AA-2, the relationship between the morphologies and luminescent properties of solid materials and molecular packing structures was elucidated.
1、合成了不同长度烷基取代的氟代喹吖啶酮(Cn-DFQA)和三氟甲基喹吖啶酮(Cn-DTFMQA)衍生物,并通过氧化喹吖啶酮中间体的方法分别获得了双三氟甲基取代(AA-1)和四个三氟甲基取代(AA-2)的芳香胺化合物。对化合物组成与结构进行了确认,考察了化合物的溶液光物理性质,获得了九种单晶。
2、以Cn-DFQA和Cn-DTFMQA化合物为构筑基元进行自组装微米材料研究。Cn-DFQA微米材料的形貌和性质明显具有烷基链长度依赖特性。单晶结构分析表明,C4-DFQA与C8-DFQA分子均通过π…π相互作用形成一维分子柱,而C10-DFQA与C16-DFQA的分子堆积结构和弱相互作用都十分类似,分子通过弱相互作用形成分子层。以C8-DTFMQA和C12-DTFMQA制备了长度超过1mm的超长微米材料,单晶研究表明分子的一维组装优势是制备超长微米材料的主要原因之一。
3、以非手性中心对称的C6-TMQA和C10-TMQA化合物为构筑基元,通过掺杂某些特定溶剂(乙醇、正丙醇、异丙醇、乙酸和丙酸)成功制备了具有扭曲形貌的自组装纤维,扭曲纤维具有热致变色性质。运用光谱、单晶及分子模拟等手段,我们提出了该系列化合物扭曲的可能起因:在掺杂溶剂存在下,喹吖啶酮分子在组装时会发生交错式的堆积导致最终扭曲结构的形成。
4、研究了三氟甲基取代芳香胺衍生物(AA-1与AA-2)的固态发光开关行为,两种化合物均具有热诱导可逆固态相转变特性并伴随发光颜色的变化。通过控制熔融样品的冷却速度可以获得不同的发光相态,此外,还观察到了两个“单晶-单晶”转变过程。通过对比单晶结构与实验现象,我们认为分子堆积结构的相互转换是获得固态发光开关的原因。我们还发现了其中一种AA-2绿色晶体具有固体蓝移发射特性,通过分子模拟我们认为在该绿色单晶中分子几何结构的较大变形导致能级差显著升高是导致该固体发射蓝移的主要原因。
Organic semiconductor materials, possessing several notable advantages including easy design and synthesis, mechanical flexibility, and low cost, have been used as active elements in optoelectronic devices such as organic light emitting diodes (OLEDs), solar cells, sensors, field effect transistors, optical waveguides and lasers. Recently, molecular materials fabricated from organic molecules through non-covalent interactions (hydrogen bondings,π-πinteractions, metal-metal interactions, etc.), have gradually become a research hotspot. Organic molecules can be prepared into molecular materials (micro-/nano-materials, thin films, single crystals, etc.) with abundant functions such as electricity, light, sensor, energy conversion, molecular machines etc, because of intermolecular non-covalent interaction. For organic solid materials, the constituent molecules may form strong intermolecular interactions and assembly packing structures resulting in that the properties of these materials are governed by the whole collective rather than by individual molecules. The performance of organic molecule-based devices strongly depends on the molecular assembly structures. Therefore, understanding and controlling molecular arrangement in solid state are fundamental issues for obtaining the solid material with desired chemical and physical properties.
1. In chapter II, four fluorinated quinacridone compounds (Cn-DFQA, n = 4, 8, 10, 16), four quinacridone derivatives substituted with trifiuoromethyl (Cn-DTFMQA, n = 4, 8, 12, 16) and two trifluoromethyl substituted aromatic amine compounds (AA-1 and AA-2) have been synthesized. All the compounds are obtained in high yields and characterized by ~1H NMR spectroscopy, mass spectra, and element analysis. The concentration-dependent photophysics properties (absorption spectra, emission spectra and the Photoluminescence quantum efficiency) of synthesized compounds in solutions have been studied in detail.
2. In chapter III, it was demonstrated that Cn-DFQA could be used as building blocks to fabricate organic luminescent micro-materials. The assembly properties of Cn-DFQA have obvious alky chain length dependent characteristic. The alky chain length has dramatic effect on the morphology of the resulted micro-materials. The molecules C4-DFQA and C8-DFQA with shorter alky chains could assemble into 1-D micro-materials, while C10-DFQA and C16-DFQA with longer alky chains aggregate into diamond and hexagonal micro-particle crystals, respectively. The emission spectra of the 1-D micro-materials formed by C4-DFQA or C8-DFQA exhibited red shift compared with that of the micro-particle crystals composed of C10-DFQA or C16-DFQA. The single crystal structure analysis revealed that in the crystals C4-DFQA and C8-DFQA there are 1-D molecular columns based on intermolecularπ…πand hydrogen bond interactions, while 2-D hydrogen bond molecular sheets are observed in the crystals C10-DFQA and C16-DFQA. The molecular packing properties of the four crystals suggest that C4-DFQA and C8-DFQA molecules have the tendency to form 1-D structure, while C10-DFQA and C16-DFQA molecules posses the characteristic to generate the sheet structures. The single crystal structures give a rational explanation for the alky chain length dependent morphology properties of the Cn-DFQA based micro materials. Therefore, it is possible to control the morphologies and emission properties of the organic micro and nano-materials through varying the molecular structures.
Self-assembled 1D nanostructures with distinct morphologies are fabricated by the deposition of Cn-DTFMQA solutions (1.0×10~(-3)M). The microstructures fabricated from C8-DTFMQA and C12-DTFMQA give ultralong 1D nanowires (more than 1 mm) with high aspect ratios. The investigation of the crystal structure suggests that DTFMQA-C8 molecules should have the tendency to aggregate into a straight liner 1-D structure in nature. The single crystal structure feature of C8-DTFMQA provided a rational explanation for the formation of the flat fibers. It is known that the energy of hydrogen bong is C=O…H-C >π…π> C-F…H-C, so the 1D aggregate tendency of C8-DTFMQA molecules is the kay factor to form ultralong micromaterials.
3. In chapter IV, we show that two achiral center-symmetrical quinacridone (QA) derivatives, N,N'-di(n-hexyl)-1,3,8,10-tetramethylquinacridone (C6TMQA) and N,N'-di(n-decyl)-1,3,8,10-tetramethylquinacridone (C10TMQA), could be employed as building blocks to fabricate well-defined twisted nanostructures by controlling the mixture solvent's composition and concentration. The bowknot-like bundles with twisted fiber arms were prepared based on C6TMQA. The uniform twisted fibers were generated from C10TMQA in ethanol/THF solution. The scanning electron microscope (SEM), UV-Vis spectra, differential scanning Calorimetry (DSC), X-ray diffraction, infrared (IR), nuclear magnetic resonance (NMR), single crystal and molecule simulations characterizations revealed that the introduction of ethanol molecules in the solution systems could induce the staggered aggregation of C6-TMQA (or C10-TMQA) molecules and the formation of twisted nanostructures. The twisted materials generated from achiral organic functional molecules may be valuable to the design and fabrication of new materials for optoelectronic applications. The twisted materials generated from achiral organic functional molecules may be valuable to the design and fabrication of new materials for optoelectronic applications.
4. In chapter V, AA-1 and AA-2 display thermo-induced and revisable solid sate phase transformation properties, which are accompanied by the switches between the different emission colors. For AA-1 or AA-2, the different phases could be obtained by controlling the solidification speed of the melted AA-1 or AA-2 sample. The red phases of AA-1 and AA-2 can undergo solid phase transfer into corresponding yellow phase of AA-1 and green AA-2 phase, respectively. The single crystal to single crystal transformation from red crystal AA-1 to yellow crystal AA-1 has been achieved. The phase dependent emission properties of AA-1 and AA-2 have been attributed to the different molecular packing properties and changeable molecular geometry for different solid phases of AA-1 and AA-2. The novel organic luminescence materials AA-1 and AA-2, which could be efficiently switched between two different luminescent phases based on the external thermal stimulation, may be employed to fabricate the display, sensing, memory devices.
In summary, we have synthesized and characterized ten novel organic light-emitting materials. Their concentration-dependent photophysical properties in solution were investigated, and nine single crystals were grown and their structures were analyzed. Through investigating the self-assembly behaviors of Cn-DFQA, Cn-DTFMQA and Cn-TMQA and the thermal induced solid-state luminescent switch behaviors of AA-1 and AA-2, the relationship between the morphologies and luminescent properties of solid materials and molecular packing structures was elucidated.
引文
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