含氮、氧建筑块的分子组装及其荧光性质研究
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摘要
本论文合成了一系列具有不同形状(包括链状、V型和三角形)的含吡啶或咪唑类配体,同时合成了β-二酮(即2,5-二取代-1,4-环己二烯醇)系列衍生物,使其与金属盐自组装,形成功能配合物,培养了一系列单晶。应用现代谱学方法, X-射线衍射分析确定了化合物和配合物的微观结构,根据微观结构来推断宏观性质,寻找分子结构与荧光性质之间的关系。具体研究内容如下:
1.含氮配体的合成:①应用Witting反应合成了4个直链型刚性配体(L1、L2、L3、L4);②应用Ullmann反应合成了2个直链型柔性配体(L5、L8)、1个以芴为中心的V型吡啶类配体(L9)和1个以三苯胺为中心的三角形吡啶类配体(L10);③用醛酮缩合反应合成了2个直链型半柔性配体(L6、L7)和1个以三苯胺为中心的三角形吡啶类配体(L11)。通过元素分析、核磁氢谱和红外确定了它们的结构(见第二章)。
同时,培养了4个中间体[2,7-二氯芴、2,7-二溴芴、三(4-溴苯基)胺和三(4-乙酰基苯基)胺]和1个配体化合物的单晶,通过X-射线衍射仪进一步确定了晶体结构。应用Mercury和diamond软件,对培养出来的单晶进行了微观结构探讨,研究其中的原子排布和分子堆积情况。研究了它们的结构与光物理性质(包括紫外、荧光和荧光寿命)之间的关系。
2.合成了三个系列32个β-二酮(即2,5-二取代-1,4-环己二烯醇)系列衍生物,通过核磁氢谱和红外确定了它们的结构。并且培养了7个化合物的单晶,通过X-射线衍射仪进一步确定了晶体结构。应用Mercury和diamond软件,对培养出来的单晶进行了微观结构探讨,研究了其中的原子排布和分子堆积情况。同时,研究了他们的结构与光物理性质(包括紫外、荧光和荧光寿命)之间的关系。
对2,5-二取代-1,4-环己二烯醇的合成方法探讨,用了不同的溶剂、催化剂及反应温度,通过比较,总结出了反应温和、产率高而且后处理简单的很适合工业化生产的合成路线(见第三章)。
3.通过分子组装,合成了5个层状结构的配合物【Cu(dippy)(ace)_2、(H_2diPPY)(p-CH_3O-bic)_2、[Pb(dipic)]n、[Cu(dipic)(H_2O)_2]_n、[Cu(pic)_2(H_2O)_4]】,3个其他结构的配合物【Cu(H_2difpy)Cl_4、Ni(difpy)(ditbu)_2、([(CH_3)_2NH_2]_3 (Cd_3Cl_9))∞】。应用Mercury和diamond软件,对这8个单晶进行了微观结构研究,Cu(dippy)(ace)_2形成一个无限延伸的“楼梯”状结构;(H_2dippy)(p-CH_3O-bic)_2,两个超分子形成一个“V”结构,多个分子沿b轴方向延伸,形成一个无限延伸的“N或M”型链;[Pb(dipic)]_n形成了一种包含三种螺旋链结构的新颖2D网状结构,螺旋链的最大辫子根数是三根链缠绕在一起的自缠绕体系。网状2D结构通过氧桥连接在一起的形成一个3 D层状结构;[Cu(dipic)(H_2O)_2]_n形成了一种包含单螺旋链结构的新颖2D网状结构;Cu(pic)_2(H_2O)_4形成了一个新颖两根分子辫的分子互穿结构。分子辫向两边延伸形成一个带状平面;Cu(H_2difpy)Cl_4形成一个“躺椅”结构,不同的“躺椅”被平行的连接在一起;Ni(difpy)(ditbu)_2形成一个“w”结构,w型结构都非常整齐的平行排布在一起;{[(CH_3)_2NH_2]_3(Cd_3Cl_9)}∞形成了一个金属线状配合物{[(CH_3)_2NH_2]_3(Cd_3Cl_9)}∞,并对它进行了量化计算(见第四章)。
4.用L_1、L_3和L_(11)与不同的有机或无机酸自组装,合成了27个超分子化合物,通过元素分析和红外确定了它们的结构;并对它们进行了光物理性质(紫外光谱、单光子荧光和单光子荧光寿命)测定,研究了他们的结构与光物理性质之间的关系。我们对对甲氧基苯甲酸对配体L_1单光子荧光光谱的影响做了仔细研究(见第五章)。
5.用L_1、L_2、L_6、L_7、L_8、L_9和L_(10)与不同金属盐自组装,共合成了113个含氮配合物;用部分β-二酮(2,5-二取代-1,4-环己二烯醇)系列衍生物与不同金属盐自组装,共合成72个含氧配合物。并分别进行了光物理性质(紫外光谱、单光子荧光和单光子荧光寿命)测定,研究了他们的结构与光物理性质之间的关系(见第六、七章)。
6.通过量化计算,从热力学的角度证明下面两个反应在自然条件下的可行性。从而推断此类反应在自然条件下的可行性(见第八章)。
In this thesis, a series of building blocks have been obtained that have different figure including chain, V shape and triangle; and -diketone( 2,5-dihydroxycyclohexa- l,4-diene-l,4-dicarboxylate) derivatives are synthesized. We utilize the known structural compounds including N and O to coordinate to metallic ion. Moreover, the crystals of a series of compounds/complexes are obtained. The crystal structures of the compounds/complexes are determined by X-ray single crystal diffraction. The information of crystal structures from X-ray single crystal diffraction are utilized to search for the relationship between structure and function. My work is summarized as follows:
1. The synthesis of Building blocks including N: (1)four lined ligands (L1、L_2、L3、L4) are synthesized by utilizing the Witting reaction; (2) two lined, a 'V shape' and a triangle ligands have been obtained by utilizing the Ullmann reaction; (3) two lined and a triangle shape ligands have been obtained by utilizing the condensation reaction.
Their structures were confirmed with IR, 1H NMR and EA. And the crystal structures of eight building blocks and four intermediates are determined by X-ray single crystal diffraction. The crystal structures are studied at micro structure. And the environment of atomic arrangement and molecular accumulation were analysed through Mercury and Diamond software. At the same time, Optical physical properties of them were mensurated and analyzed.
2. Three series of thirty-two p-diketone derivatives are synthesized. Their structures were confirmed with IR and 1H NMR. And the crystal structures of eight building blocks and four intermediates are determined by X-ray single crystal diffraction. The crystal structures are studied at micro structure. And the environment of atomic arrangement and molecular accumulation were analyzed through Mercury and Diamond softwares. At the same time, Optical physical properties of them were mensurated and analyzed.
The synthesis method of 2,5-dihydroxycyclohexa- l,4-diene-l,4-dicarboxylate are studied. Through comparison, we conclude a synthetic route of easier disposal, higher yield and milder reaction by utilizing different solvent, catalyzer and temperature of the reaction.
3. By self-assembly, five layer coordination complexes are synthesized [Cu(dippy)(ace)_2、(H_2dippy)(p-CH_3O-bic)_2、[Pb(dipic)]_n、Cu(dipic)(H_2O)_2]_n、[Cu(pic)_2(H_2O)_4]] and the other three complexes [Cu(H_2difpy)Cl_4、Ni(difpy) (ditbu)_2、{[(CH_3)_2NH_2]_3(Cd_3Cl_9)}∞]。
The eight crystal structures are studied at microstructure. And the environment of atomic arrangement and molecular accumulation were analyzed through Mercury and Diamond software5. Cu(dippy)(ace)_2 forms a 'stairway' structure. Cu(H_2difpy)Cl_4 forms a 'reclining chair' structure; The parallel 'reclining chair' structures are connected. Ni(difpy)(ditbu)2 forms a 'W structure. The parallel 'W structures are connected. (H2dippy)(p-CH3O-bic)2, two supermolecules form a 'V structure and the limitless 'M or Z' chain is connected through 'V' structure. [Pb(dipic)]n exhibits a novel 2D framework which contains three-type of helical chains with the highest-stranded number of three in the entangled system and the reticular 2D framework through oxo-bridges forms a 3D layer structure. [Cu(dipic)(H_2O)_2]_n exhibits a novel 2D framework which contains single-helix chains in the entangled system through oxo-bridges. [Cu(pic)_2(H_2O)_4] exhibits a novel 2D framework which contains double-helix in the entangled system. {[(CH_3)_2NH_2]_3(Cd_3Cl_9)}∞exhibits a ID frame- work containing metal string complexes and quantum chemical calculations were performed with GAUSSIAN 03 program.
4. Twenty-seven supermolecular complexes have been obtained by self- assembly utilizing the compounds (L_1、L_3 and L_(11)) with organic or inorganic acid. Optical physical properties of them were mensurated and analyzed. The fluorescence property of ligand L1 is influenced by 4-methoxybenzoic acid that is studied.
5. One hundred and thirteen complexes have been obtained by utilizing the ligands( L1、L_2、L6、L7、L8、L9 and L10) and seventy-two complexes have been synthesized by utilizing the ligands including 0 to coordinate to metallic ion. Optical physical properties of them were mensurated and analyzed, respectively. Through comparison, we have searched for the relationship between structure and function.
6. From thermodynamics, quantum chemical calculations were performed with GAUSSIAN 03 program. We determine the below reaction possible at room condition. Therefore, we conclude a kind of reaction feasible.
1.含氮配体的合成:①应用Witting反应合成了4个直链型刚性配体(L1、L2、L3、L4);②应用Ullmann反应合成了2个直链型柔性配体(L5、L8)、1个以芴为中心的V型吡啶类配体(L9)和1个以三苯胺为中心的三角形吡啶类配体(L10);③用醛酮缩合反应合成了2个直链型半柔性配体(L6、L7)和1个以三苯胺为中心的三角形吡啶类配体(L11)。通过元素分析、核磁氢谱和红外确定了它们的结构(见第二章)。
同时,培养了4个中间体[2,7-二氯芴、2,7-二溴芴、三(4-溴苯基)胺和三(4-乙酰基苯基)胺]和1个配体化合物的单晶,通过X-射线衍射仪进一步确定了晶体结构。应用Mercury和diamond软件,对培养出来的单晶进行了微观结构探讨,研究其中的原子排布和分子堆积情况。研究了它们的结构与光物理性质(包括紫外、荧光和荧光寿命)之间的关系。
2.合成了三个系列32个β-二酮(即2,5-二取代-1,4-环己二烯醇)系列衍生物,通过核磁氢谱和红外确定了它们的结构。并且培养了7个化合物的单晶,通过X-射线衍射仪进一步确定了晶体结构。应用Mercury和diamond软件,对培养出来的单晶进行了微观结构探讨,研究了其中的原子排布和分子堆积情况。同时,研究了他们的结构与光物理性质(包括紫外、荧光和荧光寿命)之间的关系。
对2,5-二取代-1,4-环己二烯醇的合成方法探讨,用了不同的溶剂、催化剂及反应温度,通过比较,总结出了反应温和、产率高而且后处理简单的很适合工业化生产的合成路线(见第三章)。
3.通过分子组装,合成了5个层状结构的配合物【Cu(dippy)(ace)_2、(H_2diPPY)(p-CH_3O-bic)_2、[Pb(dipic)]n、[Cu(dipic)(H_2O)_2]_n、[Cu(pic)_2(H_2O)_4]】,3个其他结构的配合物【Cu(H_2difpy)Cl_4、Ni(difpy)(ditbu)_2、([(CH_3)_2NH_2]_3 (Cd_3Cl_9))∞】。应用Mercury和diamond软件,对这8个单晶进行了微观结构研究,Cu(dippy)(ace)_2形成一个无限延伸的“楼梯”状结构;(H_2dippy)(p-CH_3O-bic)_2,两个超分子形成一个“V”结构,多个分子沿b轴方向延伸,形成一个无限延伸的“N或M”型链;[Pb(dipic)]_n形成了一种包含三种螺旋链结构的新颖2D网状结构,螺旋链的最大辫子根数是三根链缠绕在一起的自缠绕体系。网状2D结构通过氧桥连接在一起的形成一个3 D层状结构;[Cu(dipic)(H_2O)_2]_n形成了一种包含单螺旋链结构的新颖2D网状结构;Cu(pic)_2(H_2O)_4形成了一个新颖两根分子辫的分子互穿结构。分子辫向两边延伸形成一个带状平面;Cu(H_2difpy)Cl_4形成一个“躺椅”结构,不同的“躺椅”被平行的连接在一起;Ni(difpy)(ditbu)_2形成一个“w”结构,w型结构都非常整齐的平行排布在一起;{[(CH_3)_2NH_2]_3(Cd_3Cl_9)}∞形成了一个金属线状配合物{[(CH_3)_2NH_2]_3(Cd_3Cl_9)}∞,并对它进行了量化计算(见第四章)。
4.用L_1、L_3和L_(11)与不同的有机或无机酸自组装,合成了27个超分子化合物,通过元素分析和红外确定了它们的结构;并对它们进行了光物理性质(紫外光谱、单光子荧光和单光子荧光寿命)测定,研究了他们的结构与光物理性质之间的关系。我们对对甲氧基苯甲酸对配体L_1单光子荧光光谱的影响做了仔细研究(见第五章)。
5.用L_1、L_2、L_6、L_7、L_8、L_9和L_(10)与不同金属盐自组装,共合成了113个含氮配合物;用部分β-二酮(2,5-二取代-1,4-环己二烯醇)系列衍生物与不同金属盐自组装,共合成72个含氧配合物。并分别进行了光物理性质(紫外光谱、单光子荧光和单光子荧光寿命)测定,研究了他们的结构与光物理性质之间的关系(见第六、七章)。
6.通过量化计算,从热力学的角度证明下面两个反应在自然条件下的可行性。从而推断此类反应在自然条件下的可行性(见第八章)。
In this thesis, a series of building blocks have been obtained that have different figure including chain, V shape and triangle; and -diketone( 2,5-dihydroxycyclohexa- l,4-diene-l,4-dicarboxylate) derivatives are synthesized. We utilize the known structural compounds including N and O to coordinate to metallic ion. Moreover, the crystals of a series of compounds/complexes are obtained. The crystal structures of the compounds/complexes are determined by X-ray single crystal diffraction. The information of crystal structures from X-ray single crystal diffraction are utilized to search for the relationship between structure and function. My work is summarized as follows:
1. The synthesis of Building blocks including N: (1)four lined ligands (L1、L_2、L3、L4) are synthesized by utilizing the Witting reaction; (2) two lined, a 'V shape' and a triangle ligands have been obtained by utilizing the Ullmann reaction; (3) two lined and a triangle shape ligands have been obtained by utilizing the condensation reaction.
Their structures were confirmed with IR, 1H NMR and EA. And the crystal structures of eight building blocks and four intermediates are determined by X-ray single crystal diffraction. The crystal structures are studied at micro structure. And the environment of atomic arrangement and molecular accumulation were analysed through Mercury and Diamond software. At the same time, Optical physical properties of them were mensurated and analyzed.
2. Three series of thirty-two p-diketone derivatives are synthesized. Their structures were confirmed with IR and 1H NMR. And the crystal structures of eight building blocks and four intermediates are determined by X-ray single crystal diffraction. The crystal structures are studied at micro structure. And the environment of atomic arrangement and molecular accumulation were analyzed through Mercury and Diamond softwares. At the same time, Optical physical properties of them were mensurated and analyzed.
The synthesis method of 2,5-dihydroxycyclohexa- l,4-diene-l,4-dicarboxylate are studied. Through comparison, we conclude a synthetic route of easier disposal, higher yield and milder reaction by utilizing different solvent, catalyzer and temperature of the reaction.
3. By self-assembly, five layer coordination complexes are synthesized [Cu(dippy)(ace)_2、(H_2dippy)(p-CH_3O-bic)_2、[Pb(dipic)]_n、Cu(dipic)(H_2O)_2]_n、[Cu(pic)_2(H_2O)_4]] and the other three complexes [Cu(H_2difpy)Cl_4、Ni(difpy) (ditbu)_2、{[(CH_3)_2NH_2]_3(Cd_3Cl_9)}∞]。
The eight crystal structures are studied at microstructure. And the environment of atomic arrangement and molecular accumulation were analyzed through Mercury and Diamond software5. Cu(dippy)(ace)_2 forms a 'stairway' structure. Cu(H_2difpy)Cl_4 forms a 'reclining chair' structure; The parallel 'reclining chair' structures are connected. Ni(difpy)(ditbu)2 forms a 'W structure. The parallel 'W structures are connected. (H2dippy)(p-CH3O-bic)2, two supermolecules form a 'V structure and the limitless 'M or Z' chain is connected through 'V' structure. [Pb(dipic)]n exhibits a novel 2D framework which contains three-type of helical chains with the highest-stranded number of three in the entangled system and the reticular 2D framework through oxo-bridges forms a 3D layer structure. [Cu(dipic)(H_2O)_2]_n exhibits a novel 2D framework which contains single-helix chains in the entangled system through oxo-bridges. [Cu(pic)_2(H_2O)_4] exhibits a novel 2D framework which contains double-helix in the entangled system. {[(CH_3)_2NH_2]_3(Cd_3Cl_9)}∞exhibits a ID frame- work containing metal string complexes and quantum chemical calculations were performed with GAUSSIAN 03 program.
4. Twenty-seven supermolecular complexes have been obtained by self- assembly utilizing the compounds (L_1、L_3 and L_(11)) with organic or inorganic acid. Optical physical properties of them were mensurated and analyzed. The fluorescence property of ligand L1 is influenced by 4-methoxybenzoic acid that is studied.
5. One hundred and thirteen complexes have been obtained by utilizing the ligands( L1、L_2、L6、L7、L8、L9 and L10) and seventy-two complexes have been synthesized by utilizing the ligands including 0 to coordinate to metallic ion. Optical physical properties of them were mensurated and analyzed, respectively. Through comparison, we have searched for the relationship between structure and function.
6. From thermodynamics, quantum chemical calculations were performed with GAUSSIAN 03 program. We determine the below reaction possible at room condition. Therefore, we conclude a kind of reaction feasible.
引文
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