基于唑类二羧酸配体的配位聚合物的合成，结构与性质研究
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摘要
配位聚合物作为一种新型的功能材料，近年来受到各国学者的广泛关注，其独特的结构和功能可设计性等特点，使这类材料在气体储存、催化、光学、磁学、气体选择性吸附与分离等方面都有着潜在的应用价值。随着人们对该类材料的结构进行不同功能基团的修饰，其化学性质和物理性质发生相应改变，或同时兼具多种功能，使其应用范围逐渐扩大，如近些年在药物释放，生物传感方面等都展现出一定的应用价值。因此，通过研究配位聚合物的结构特点及合成规律，合理的设计不同的基团，由此导致丰富的性质，对构筑功能型金属有机配位聚合物材料具有一定的科学研究意义。
金属-有机配位聚合物主要由金属及有机配体构成，因此，选择合适的金属中心和设计不同的有机配体对配位聚合物的构筑至关重要。本文设计合成含N，O，S等元素的唑类羧酸1,2,3-三氮唑-4,5-二羧酸(H_3tzdc)和1,2,5-噻二唑-3,4-二羧酸(H_2tdc)作为有机配体，与不同族数的金属原子（主族金属In、镧系稀土金属、过渡金属）配位，在溶剂热的条件下，通过改变溶剂的极性，pH值，反应温度，以及引入不同有机胺等反应条件，构筑了19个金属-有机配位聚合物，并根据其结构特点，对部分化合物进行了气体吸附和荧光性质的研究。本论文的主要研究工作如下：
1.在溶剂热条件下，以H_3tzdc和H_2tdc作为有机配体，铟离子作为金属源，通过引入三种不同的有机胺，得到了四种配位聚合物1-4。化合物1-3均是以H_3tzdc为有机配体构筑的In-MOFs，化合物4是利用H_2tdc为有机配体构筑的In-MOFs。化合物1结构中引入了端基螯合配体1,2-环己二胺（1,2-DACH）与硝酸铟配位形成了一个具有4个金属中心，4个有机配体及4个有机胺的金属有机四边形，通过K+及氢键作用连接成了3D网状结构。该结构中每个零维的金属有机四边形通过分子间氢键作用连接成具有类分子筛rho拓扑学结构的3D超分子化合物。化合物2和3均是在有机胺分子TMDP的存在下，获得的MOFs材料。化合物2中，三个有机配体与三个甲酸分子和六个In~(3+)连接形成了一个六核铟簇，并以此作为无机结构基元，通过tzdc_(3-)作为有机连接体，组装了具有22A的纳米级孔道的3D骨架化合物，并展现出新颖的具有(4,6)-连接的拓扑学结构。化合物3中，12个有机配体与8个金属形成了一个金属有机立方体，每个零维的立方体与有机胺分子通过氢键作用形成了具有四重互穿结构的3D超分子骨架化合物，单重结构具有27.9×13.8A的孔道，并展现出pcu拓扑学结构。化合物4结构中，通过引入有机胺分子邻菲罗啉，与In~(3+)配位形成了一个由2个铟离子，2个有机配体以及4个有机胺分子构成的金属有机四边形，并通过氢键作用相互连接形成了2D层状结构。化合物1-4都具有较高的热稳定性，同时化合物1和2展现出一定的气体吸附性质，化合物2和3在可见光区域展现了一定的荧光性质。
2.在溶剂热体系下，我们以H_2tdc为有机配体，与镧系稀土金属构筑了12个化合物5-16。化合物5-16是在相似的反应条件下，通过改变反应溶剂的极性，有机配体与金属源的比例，以及引入了线型的第二有机配体反丁烯二酸的情况下，展现出三种不同的3D结构，实现了化合物由致密结构到微孔结构的转变。化合物5-12是以镧，铈，鐠，钕，钐，铕，钆，铽为金属源进行构筑的化合物，金属中心与配体连接成为1D zigzag链状结构，并通过钾离子和水分子连接成三维的具有moc拓扑学结构的化合物。13-14是以镧和铈为金属源，引入反丁烯二酸作为桥连配体，通过金属中心与tdc~(2-)形成了一个与化合物5-12相似的1D链状结构，利用反丁烯二酸连接成了具有dia拓扑学结构的3D网状结构。15和16同样是以镧和铈为金属源构筑的化合物，该结构中，有机配体与金属中心形成了左/右手螺旋链，链与链之间相互连接成为具有(3,4,5)-连接的新颖拓扑学结构的3D骨架化合物。由于有机配体具有良好的“天线效应”，基于钐，铕，铽为金属中心的Ln-MOFs具有良好的发光性质，分别展现出橙色，红色和绿色的荧光性能。
3.在溶剂热的条件下，以H_3tzdc为有机配体，过渡金属镉，铜为金属源构筑了3个新颖结构的化合物17-19。化合物17是以镉为金属源，与有机配体螯合配位形成了一个四核镉簇，并以此为次级结构基元，通过有机配体相连形成了一个具有单节点5-连接的bnn拓扑学结构的3D网络化合物。18和19是以铜为金属源构筑的MOFs材料，化合物18中，4个铜原子与4个有机配体相连形成一个类卟啉环的四边形，并以此为次级结构基元通过铜离子相连形成了具有pto拓扑学结构的3D网络化合物。化合物19中，6个配体和12个金属中心形成了一个类Kagomé层，彼此相连形成2D层状结构，通过引入有机胺4,4’-联吡啶将其柱支撑为3D新颖的(3,4)-连接的拓扑学结构。化合物17和19具有较高的热稳定性，17除了具有气体吸附性质外，还展现出荧光响应有机小分子的性质。
本论文中，利用次级结构单元法，合成了19个金属-有机配位聚合物，并对其进行了详细的表征，通过其特有的结构特点，讨论了配体与金属之间的配位模式对其结构的影响，丰富了配位聚合物材料的种类及拓扑学信息，部分化合物展现出的气体吸附和荧光性质也为这类材料的进一步应用提供了一定的实验依据。
Coordination Polymers (CPs), as a novel functional material, arouse extensive attentionrecently. Their permanent porosity, high surface areas, fine-tunable pore structures, andadjustable chemical functionalities make them possessing potential applications in gas storage,catalysis, gas adsorption and separation, luminescence, and magnetism. As diverse organicligands were explored, and postsynthesis or modification for MOFs materials, the chemicaland physical properties would be improved and expanded the application scope. Recently, italso possessed the applications in drug release and sensor in biology. Therefore, assemblingMOFs with unique structures and tailor-making properties by rational design have a greatsignificance in developing novel materials.
Herein, we utilize two organic ligands,1,2,3-triazole-4,5-dicarboxylic acid (H_3tzdc) and1,2,5-thiadiazole-3,4-dicarboxylic acid (H_2tdc) coordinated with different types of metalcenters (indium, lanthanide, and transition metal) to construct novel MOFs materials undersolvothermal conditions.19compounds were synthesized by changing the solvent polarity,pH value, temperature, and inducing different organic amine. The properties such as gasadsorption, luminescence for some compounds were investigated. We get the following threeaspects results:
1. Four indium-organic frameworks1-4were solvothermally synthesized based on H_3tzdcand H_2tdc ligands, respectively, by inducing three types of organic amine. In compound1,four1,2-DACH molecules serving as terminal ligands in combination with four In~(3+)ions andfour tzdc_(3-)ligands generate a metal-organic square (MOS), and MOS was linked via K+toform a3D framework. Each MOS connected each other via16hydrogen bonds to produce azeolite-like rho topology. Compounds2and3have a similar reaction conditions with H_3tzdcligand and TMDP molecules. In compound2, three tzdc_(3-)ligands and three formic acidmolecules, as well as six In~(3+)composed a hexanuclear cluster, and the ligand linked to thehexanuclear cluster to form a3D framework with a22A hexagonal-shaped nanopores. The ~framework exhibited a novel (4,6)-connected net. In compound3, twelve tzdc_(3-)ligandscoordinated with eight In~(3+)to generate a metal-organic cubic (MOC), and each MOCconnected each other by hydrogen bonds to form a3D supramolecular structure with four-foldInterpenetration. Each single fold structure possessing a pcu topology has a channel withdiameter of27.9×13.8A. Compound4based on H_2tdc ligand was obtained by inducingorganic amine Phen. In compound4, each MOS, constructed by two In~(3+), two tdc~(2-)ligandsand four Phen molecules, as the secondary building unit, connected each other via hydrogenbonds to form a2D layer structure. Compounds1-4with high thermal stability werecharacterized and formulated by elemental analysis, thermogravimetric analysis andsingle-crystal X-ray diffraction. Compounds1and2exhibited gas adsorption properties, andcompounds2and3displayed luminescent properties.
2. Twelve novel three-dimensional (3D) lanthanide metal-organic frameworks5-16withformula [LnK(C_4N_2O_4S)2(H_2O)_2](H_2O)_(0.5)(Ln=La (5), Ce (6), Pr (7), Nd (8), Sm (9), Eu (10),Gd (11), Tb (12)),[LnK(C_4N_2O_4S)(C_4O_4)(H_2O)_2](H_2O)_(0.5)(Ln=La (13), Ce (14)), and[Ln_2(C_4N_2O_4S)_3(H_2O)](H_2O)(Ln=La (15), Ce (16)), were solvothermally synthesized by2,1,3-thiadiazole-4,5-dicarboxylate (H_2tdc) ligand with corresponding lanthanide nitrate.Three types of the structure from nonporous to microporous frameworks were exhibited withthe changing of solvent polarity, the ratio of ligand and metal center, and inducing the secondliner ligand fumaric acid. Compounds5-12with the isostructure (structure I) contain a1Dzigzag chain along the b axis, which connected by K~+and pillared water molecules to form3D frameworks with moc topology. Compounds13and14are isomorphous coordinationpolymers (structure II) possessing a similar zigzag chain, which linked via the coligandfumaric acid to construct3D frameworks with dia topology, while compounds15-16(structure III) are isomorphous coordination polymers. They possess a1D right-left helicalchains along the b axis, and the right-left helical chains alternatively linked to form a3Dframework with a new (3,4,5)-connected topology. As the antenna effect of the H_2tdc ligand,the luminescent property shows that compounds9,10,12displays intense orange, red andgreen luminescence and exhibits the typical Sm~（3+）, Eu~（3+）and Tb~（3+）ion emission, respectively.
3. Three transition metal-organic frameworks17-19were solvothermally synthesized byH_3tzdc ligand. Compound17based on Cd~(2+), contained a tetranuclear cadmium cluster, and the cluster was connected via ligand to form a3D framework with bnn topology. Bothcompounds18and19were obtained by Cu~(2+). In compound18, four Cu~(2+)and four ligandscomposed a unique metalloporphyrin-like plane, resulting in a3D framework with ptotopology. In compound19, twelve Cu~(2+)and six tzdc~(2-)ligands form a Kagomé-like plane,leading to a2D layer, thus4,4’-bpy was induced as the pillers to hold the layers to generatethe3D framework, and the structure possessed a new topology with the (3,4)-connected net.Compounds17-19were characterized and formulated by elemental analysis,thermogravimetric analysis and single-crystal X-ray diffraction. Compound17, with highhydrothermal stability and open Cd sites, has been found to exhibit luminescent responsetoward different organic solvents, and it also displayed gas adsorption property.
In summary, we utilized secondary building unit approach to synthesized19coordinationpolymers in solvothermal conditions. The results described here illustrate the influence of thevarious coordination modes to the unique structures, and the experimental data enriched thestructure and topology information of MOFs materials. The gas adsorption properties andluminescent properties provide value for the continuous development of functional MOFs.
金属-有机配位聚合物主要由金属及有机配体构成，因此，选择合适的金属中心和设计不同的有机配体对配位聚合物的构筑至关重要。本文设计合成含N，O，S等元素的唑类羧酸1,2,3-三氮唑-4,5-二羧酸(H_3tzdc)和1,2,5-噻二唑-3,4-二羧酸(H_2tdc)作为有机配体，与不同族数的金属原子（主族金属In、镧系稀土金属、过渡金属）配位，在溶剂热的条件下，通过改变溶剂的极性，pH值，反应温度，以及引入不同有机胺等反应条件，构筑了19个金属-有机配位聚合物，并根据其结构特点，对部分化合物进行了气体吸附和荧光性质的研究。本论文的主要研究工作如下：
1.在溶剂热条件下，以H_3tzdc和H_2tdc作为有机配体，铟离子作为金属源，通过引入三种不同的有机胺，得到了四种配位聚合物1-4。化合物1-3均是以H_3tzdc为有机配体构筑的In-MOFs，化合物4是利用H_2tdc为有机配体构筑的In-MOFs。化合物1结构中引入了端基螯合配体1,2-环己二胺（1,2-DACH）与硝酸铟配位形成了一个具有4个金属中心，4个有机配体及4个有机胺的金属有机四边形，通过K+及氢键作用连接成了3D网状结构。该结构中每个零维的金属有机四边形通过分子间氢键作用连接成具有类分子筛rho拓扑学结构的3D超分子化合物。化合物2和3均是在有机胺分子TMDP的存在下，获得的MOFs材料。化合物2中，三个有机配体与三个甲酸分子和六个In~(3+)连接形成了一个六核铟簇，并以此作为无机结构基元，通过tzdc_(3-)作为有机连接体，组装了具有22A的纳米级孔道的3D骨架化合物，并展现出新颖的具有(4,6)-连接的拓扑学结构。化合物3中，12个有机配体与8个金属形成了一个金属有机立方体，每个零维的立方体与有机胺分子通过氢键作用形成了具有四重互穿结构的3D超分子骨架化合物，单重结构具有27.9×13.8A的孔道，并展现出pcu拓扑学结构。化合物4结构中，通过引入有机胺分子邻菲罗啉，与In~(3+)配位形成了一个由2个铟离子，2个有机配体以及4个有机胺分子构成的金属有机四边形，并通过氢键作用相互连接形成了2D层状结构。化合物1-4都具有较高的热稳定性，同时化合物1和2展现出一定的气体吸附性质，化合物2和3在可见光区域展现了一定的荧光性质。
2.在溶剂热体系下，我们以H_2tdc为有机配体，与镧系稀土金属构筑了12个化合物5-16。化合物5-16是在相似的反应条件下，通过改变反应溶剂的极性，有机配体与金属源的比例，以及引入了线型的第二有机配体反丁烯二酸的情况下，展现出三种不同的3D结构，实现了化合物由致密结构到微孔结构的转变。化合物5-12是以镧，铈，鐠，钕，钐，铕，钆，铽为金属源进行构筑的化合物，金属中心与配体连接成为1D zigzag链状结构，并通过钾离子和水分子连接成三维的具有moc拓扑学结构的化合物。13-14是以镧和铈为金属源，引入反丁烯二酸作为桥连配体，通过金属中心与tdc~(2-)形成了一个与化合物5-12相似的1D链状结构，利用反丁烯二酸连接成了具有dia拓扑学结构的3D网状结构。15和16同样是以镧和铈为金属源构筑的化合物，该结构中，有机配体与金属中心形成了左/右手螺旋链，链与链之间相互连接成为具有(3,4,5)-连接的新颖拓扑学结构的3D骨架化合物。由于有机配体具有良好的“天线效应”，基于钐，铕，铽为金属中心的Ln-MOFs具有良好的发光性质，分别展现出橙色，红色和绿色的荧光性能。
3.在溶剂热的条件下，以H_3tzdc为有机配体，过渡金属镉，铜为金属源构筑了3个新颖结构的化合物17-19。化合物17是以镉为金属源，与有机配体螯合配位形成了一个四核镉簇，并以此为次级结构基元，通过有机配体相连形成了一个具有单节点5-连接的bnn拓扑学结构的3D网络化合物。18和19是以铜为金属源构筑的MOFs材料，化合物18中，4个铜原子与4个有机配体相连形成一个类卟啉环的四边形，并以此为次级结构基元通过铜离子相连形成了具有pto拓扑学结构的3D网络化合物。化合物19中，6个配体和12个金属中心形成了一个类Kagomé层，彼此相连形成2D层状结构，通过引入有机胺4,4’-联吡啶将其柱支撑为3D新颖的(3,4)-连接的拓扑学结构。化合物17和19具有较高的热稳定性，17除了具有气体吸附性质外，还展现出荧光响应有机小分子的性质。
本论文中，利用次级结构单元法，合成了19个金属-有机配位聚合物，并对其进行了详细的表征，通过其特有的结构特点，讨论了配体与金属之间的配位模式对其结构的影响，丰富了配位聚合物材料的种类及拓扑学信息，部分化合物展现出的气体吸附和荧光性质也为这类材料的进一步应用提供了一定的实验依据。
Coordination Polymers (CPs), as a novel functional material, arouse extensive attentionrecently. Their permanent porosity, high surface areas, fine-tunable pore structures, andadjustable chemical functionalities make them possessing potential applications in gas storage,catalysis, gas adsorption and separation, luminescence, and magnetism. As diverse organicligands were explored, and postsynthesis or modification for MOFs materials, the chemicaland physical properties would be improved and expanded the application scope. Recently, italso possessed the applications in drug release and sensor in biology. Therefore, assemblingMOFs with unique structures and tailor-making properties by rational design have a greatsignificance in developing novel materials.
Herein, we utilize two organic ligands,1,2,3-triazole-4,5-dicarboxylic acid (H_3tzdc) and1,2,5-thiadiazole-3,4-dicarboxylic acid (H_2tdc) coordinated with different types of metalcenters (indium, lanthanide, and transition metal) to construct novel MOFs materials undersolvothermal conditions.19compounds were synthesized by changing the solvent polarity,pH value, temperature, and inducing different organic amine. The properties such as gasadsorption, luminescence for some compounds were investigated. We get the following threeaspects results:
1. Four indium-organic frameworks1-4were solvothermally synthesized based on H_3tzdcand H_2tdc ligands, respectively, by inducing three types of organic amine. In compound1,four1,2-DACH molecules serving as terminal ligands in combination with four In~(3+)ions andfour tzdc_(3-)ligands generate a metal-organic square (MOS), and MOS was linked via K+toform a3D framework. Each MOS connected each other via16hydrogen bonds to produce azeolite-like rho topology. Compounds2and3have a similar reaction conditions with H_3tzdcligand and TMDP molecules. In compound2, three tzdc_(3-)ligands and three formic acidmolecules, as well as six In~(3+)composed a hexanuclear cluster, and the ligand linked to thehexanuclear cluster to form a3D framework with a22A hexagonal-shaped nanopores. The ~framework exhibited a novel (4,6)-connected net. In compound3, twelve tzdc_(3-)ligandscoordinated with eight In~(3+)to generate a metal-organic cubic (MOC), and each MOCconnected each other by hydrogen bonds to form a3D supramolecular structure with four-foldInterpenetration. Each single fold structure possessing a pcu topology has a channel withdiameter of27.9×13.8A. Compound4based on H_2tdc ligand was obtained by inducingorganic amine Phen. In compound4, each MOS, constructed by two In~(3+), two tdc~(2-)ligandsand four Phen molecules, as the secondary building unit, connected each other via hydrogenbonds to form a2D layer structure. Compounds1-4with high thermal stability werecharacterized and formulated by elemental analysis, thermogravimetric analysis andsingle-crystal X-ray diffraction. Compounds1and2exhibited gas adsorption properties, andcompounds2and3displayed luminescent properties.
2. Twelve novel three-dimensional (3D) lanthanide metal-organic frameworks5-16withformula [LnK(C_4N_2O_4S)2(H_2O)_2](H_2O)_(0.5)(Ln=La (5), Ce (6), Pr (7), Nd (8), Sm (9), Eu (10),Gd (11), Tb (12)),[LnK(C_4N_2O_4S)(C_4O_4)(H_2O)_2](H_2O)_(0.5)(Ln=La (13), Ce (14)), and[Ln_2(C_4N_2O_4S)_3(H_2O)](H_2O)(Ln=La (15), Ce (16)), were solvothermally synthesized by2,1,3-thiadiazole-4,5-dicarboxylate (H_2tdc) ligand with corresponding lanthanide nitrate.Three types of the structure from nonporous to microporous frameworks were exhibited withthe changing of solvent polarity, the ratio of ligand and metal center, and inducing the secondliner ligand fumaric acid. Compounds5-12with the isostructure (structure I) contain a1Dzigzag chain along the b axis, which connected by K~+and pillared water molecules to form3D frameworks with moc topology. Compounds13and14are isomorphous coordinationpolymers (structure II) possessing a similar zigzag chain, which linked via the coligandfumaric acid to construct3D frameworks with dia topology, while compounds15-16(structure III) are isomorphous coordination polymers. They possess a1D right-left helicalchains along the b axis, and the right-left helical chains alternatively linked to form a3Dframework with a new (3,4,5)-connected topology. As the antenna effect of the H_2tdc ligand,the luminescent property shows that compounds9,10,12displays intense orange, red andgreen luminescence and exhibits the typical Sm~（3+）, Eu~（3+）and Tb~（3+）ion emission, respectively.
3. Three transition metal-organic frameworks17-19were solvothermally synthesized byH_3tzdc ligand. Compound17based on Cd~(2+), contained a tetranuclear cadmium cluster, and the cluster was connected via ligand to form a3D framework with bnn topology. Bothcompounds18and19were obtained by Cu~(2+). In compound18, four Cu~(2+)and four ligandscomposed a unique metalloporphyrin-like plane, resulting in a3D framework with ptotopology. In compound19, twelve Cu~(2+)and six tzdc~(2-)ligands form a Kagomé-like plane,leading to a2D layer, thus4,4’-bpy was induced as the pillers to hold the layers to generatethe3D framework, and the structure possessed a new topology with the (3,4)-connected net.Compounds17-19were characterized and formulated by elemental analysis,thermogravimetric analysis and single-crystal X-ray diffraction. Compound17, with highhydrothermal stability and open Cd sites, has been found to exhibit luminescent responsetoward different organic solvents, and it also displayed gas adsorption property.
In summary, we utilized secondary building unit approach to synthesized19coordinationpolymers in solvothermal conditions. The results described here illustrate the influence of thevarious coordination modes to the unique structures, and the experimental data enriched thestructure and topology information of MOFs materials. The gas adsorption properties andluminescent properties provide value for the continuous development of functional MOFs.
引文
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