偶氮配体构筑金属配合物的结构与固态荧光性能
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摘要
偶氮化合物由于具有很好的荧光性能一直受到人们的青睐，但是由于偶氮键在较低温度下就会断裂而大大影响了它的应用。本研究通过采用溶剂(水)热合成法，选用3种含偶氮基衍生物的配体与I/IIB族金属离子配位合成了16种新型配位聚合物。通过元素分析、单晶X-射线衍射、红外光谱分析和粉末X-射线衍射对晶体结构进行了表征，对配位聚合物的热稳定性和荧光性质进行了测量、理论计算及分析。研究了这些配合物的合成条件、配体的配位模式、氢键和π-π堆积相互作用等因素对偶氮金属配位聚合物性能的影响，目的在于合成能够在较高温度下仍能稳定存在的偶氮类配合物，并通过金属与配体的相互作用将所合成的配合物发射光谱相对于配体向可见光方向移动，从而为偶氮类化合物的实际应用提供更广的应用前景。
采用4-[(8-羟基-5-喹啉)偶氮]-苯磺酸(H2L1)为配体，与金属Cu、Cd和Zn离子合成10个配合物：[Cu(L1)(en)]·0.5H2O (1),[Cu(L1)2][Cu(en)2]·2H2O (2),[Zn(L1)(H2O)4](3),{[Cd(L1)(en)]·EtOH}n (4),{[Cd(L1)(H2O)2]·H2O}n (5),{[Cd2(L1)2(en)2(H2O)2]·3H2O}n (6),{[Cd(L1)(en)]·DMF}n (7),[Zn3(L1)2(OH)2(H2O)6]n (8),[Zn(L1)(H2O)]n (9)和[Zn(M1)2](10)。配合物1、2、3、10为零维结构，配合物4和5为一维梯形链状结构，配合物6为一维zig-zag链状结构，配合物7和8为一维双金属链状结构，配合物9为三维结构，配合物1~8和10通过氢键和π-π堆积相互作用均连接形成了三维的超分子网络结构。讨论了配体的配位模式对所形成的配合物结构的影响。从结构描述可知，磺酸基团的配位情况对配合物的空间构型起着重要作用。配合物10是由于配体在碱性条件下发生硝基化原位反应而获得的。配合物1~9的热稳定性相对于配体H2L1具有明显的提高。配合物1~2的荧光性质主要来自于配体对金属的电荷转移，与H2L1配体相比发生了较大的蓝移，呈现紫色荧光。并且，配体H2L1与二价铜离子作用会有特殊的显色反应，提供了一种荧光灵敏、肉眼可见、简便型检测铜离子的有效方法。配合物3~9的荧光性质主要来自于配体内电荷的转移。配合物1~9的荧光数据表明，配合物相对于H2L1配体的发射光谱略倾向于蓝移。对配合物1、2、3和10进行了荧光性质的理论计算。
采用4-[(8-羟基-5-喹啉)偶氮]-苯甲酸(H2L2)为配体，与金属Zn和Cd离子合成2个配合物：[Zn(L2)(H2O)2]n (11)和{[Cd(L2)(H2O)]·H2O}n (12)。配合物11为一维zig-zag链状结构，配合物12为二维层状结构，配合物11~12通过氢键和π-π堆积相互作用均连接形成了三维的超分子网络结构。讨论了配体的配位模式对所形成的配合物结构的影响。配合物11~12的热稳定性相对于配体H2L2具有明显的提高。配合物11~12的发射光谱相对于配体H2L2几乎没有发生改变，配合物的荧光性质主要来自于配体内的电荷转移。
采用偶氮苯-4,4'-二羧酸(H2L3)为配体，与金属Cd、Cu和Ag离子合成4种配合物：{[Cd2(L3)2(en)2]·DMF}n (13),[Cu(L3)(en)]n (14),{[Cu(L3)(phen)(H2O)]·DMA}n (15)和[Ag(L3)0.5]n (16)。配合物13~15为一维zig-zag链状结构，通过氢键和π-π堆积相互作用连接形成了三维的超分子网络结构，配合物16为三维结构。讨论了辅助配体乙二胺或1,10-邻菲罗啉对所形成的配合物结构的影响。配合物13~15的热稳定性相对于配体H2L3具有明显的提高。配合物13~15的发射光谱相对于配体H2L3均发生了较大红移，呈现蓝色荧光，荧光性质主要来自于配体对金属的电荷转移。
Azo compounds with good fluorescent properties have been attracting much attention in past decades. Due to their relatively low thermal stability, the application of azo compounds is limited. In this work, sixteen sorts of novel coordination polymers by solvothermal (hydrothermal) method have been prepared by reacting three types of azo-containing derivatives as the ligands with I/IIB metal ion. The structures of crystals were characterized by elemental analysis, single-crystal X-ray diffraction, infrared (IR) spectra and powder X-ray diffractions (PXRD). Thermal stability and fluorescent performance of coordination polymers were measured, calculated and analyzed. The synthetic conditions, the coordination model of ligand, hydrogen bonding and π-π stacking interactions were discussed to reveal the effects on azo coordination polymers applications in order to obtain stable azo compounds under high temperature. The emission spectra of coordination polymers move to the direction of visible light caused by the interaction of metals and ligands, which provides a wider application prospect for the practical application of azo compounds.
4-[(8-hydroxy-5-quinolinyl)azo]-benzenesulfonic acid (H2L1) as ligand reacts with Cu, Cd and Zn to synthesize ten sorts of novel coordination polymers:[Cu(L1)(en)]·0.5H2O (1),[Cu(L1)2][Cu(en)2]·2H2O (2),[Zn(L1)(H2O)4](3),{[Cd(L1)(en)]·EtOH}n (4),{[Cd(L1)(H2O)2]·H2O}n (5),{[Cd2(L1)2(en)2(H2O)2]·3H2O}n (6),{[Cd(L1)(en)]·DMF}n (7),[Zn3(L1)2(OH)2(H2O)6]n (8),[Zn(L1)(H2O)]n (9) and [Zn(M1)2](10). Compounds1,2,3and10exhibit zero-dimensional (0D) structure. Compounds4and5display infinite one-dimensional (1D) ladder-shaped chain structures. Compound6is1D zig-zag chain structure. Compounds7and8exhibit infinite1D double-metal chain structures. Compound9is a three-dimensional (3D) structure. Compounds1~8and10are further connected through hydrogen bonding and π-π interactions into3D supramolecular networks. The coordination model of ligand was discussed the effect of compound structure. From the description of the structure, the coordination model of sulfonate groups plays an important role in the structure of coordination compounds. Compound10was synthesized under the alkaline condition, which ligand was in situ reaction. The thermal stabilities of compounds1~9have an obvious enhancement with respect to H2L1ligand. The fluorescent properties of compounds1~2mainly come from the ligand-to-metal charge transfer, which have blue shift to H2L1ligand, showing violet fluorescence. The reaction between H2L1ligand and copper(II) ion leads to a sensitive fluorescent, visible to the naked eye and simple effective method of the detection of copper ion. The fluorescent properties of compounds3~9mainly come from the ligand-to-ligand charge transfer. The fluorescent data of compounds1~9indicate that the emission spectra of coordination compounds slightly inclined to blue shift to the H2L1ligand. The theoretical calculation of fluorescent spectra of compounds1,2,3and10were performed.
4-[(8-hydroxy-5-quinolinyl)azo]-benzoic acid (H2L2) as ligand reacts with Zn and Cd to synthesize two sorts of novel coordination polymers:[Zn(L2)(H2O)2]n (11) and {[Cd(L2)(H2O)]·H2O}n (12). Compound11exhibits1D zig-zag chain structure. Compound12is two-dimensional (2D) layer structure. Compounds11~12are further connected through hydrogen bonding and π-π interactions into3D supramolecular networks. The coordination model of ligand was studied to reveal the effect on compound structure. The thermal satbility properties of compounds11~12have an obvious enhancement to H2L2ligand. The emission spectra of compounds11~12have scarcely change to H2L2ligand. The fluorescent properties of compounds11~12mainly come from the charge transfer from ligand to ligand.
Azobenzene-4,4'-dicarboxylate (H2L3) as ligand reacts with Cd, Cu and Ag to synthesize four sorts of novel coordination polymers:{[Cd2(L3)2(en)2]·DMF}n (13),[Cu(L3)(en)]n (14),{[Cu(L3)(phen)(H2O)]·DMA}n (15) and [Ag(L3)0.5]n (16). Compounds13~15exhibit1D zig-zag chain structures, which are further connected through hydrogen bonding and π-π interactions into3D supramolecular networks. Compound16is3D structure. Ethylenediamine and1,10-phenanthroline as auxiliary ligands were studied to reveal the effect on compound structure. The thermal stability properties of compounds13~15have an obvious enhancement to H2L3ligand. The fluorescent properties of compounds13~15mainly come from the charge transfer from ligand to metal, which have red shift with respect to H2L3ligand, showing blue fluorescence.
采用4-[(8-羟基-5-喹啉)偶氮]-苯磺酸(H2L1)为配体，与金属Cu、Cd和Zn离子合成10个配合物：[Cu(L1)(en)]·0.5H2O (1),[Cu(L1)2][Cu(en)2]·2H2O (2),[Zn(L1)(H2O)4](3),{[Cd(L1)(en)]·EtOH}n (4),{[Cd(L1)(H2O)2]·H2O}n (5),{[Cd2(L1)2(en)2(H2O)2]·3H2O}n (6),{[Cd(L1)(en)]·DMF}n (7),[Zn3(L1)2(OH)2(H2O)6]n (8),[Zn(L1)(H2O)]n (9)和[Zn(M1)2](10)。配合物1、2、3、10为零维结构，配合物4和5为一维梯形链状结构，配合物6为一维zig-zag链状结构，配合物7和8为一维双金属链状结构，配合物9为三维结构，配合物1~8和10通过氢键和π-π堆积相互作用均连接形成了三维的超分子网络结构。讨论了配体的配位模式对所形成的配合物结构的影响。从结构描述可知，磺酸基团的配位情况对配合物的空间构型起着重要作用。配合物10是由于配体在碱性条件下发生硝基化原位反应而获得的。配合物1~9的热稳定性相对于配体H2L1具有明显的提高。配合物1~2的荧光性质主要来自于配体对金属的电荷转移，与H2L1配体相比发生了较大的蓝移，呈现紫色荧光。并且，配体H2L1与二价铜离子作用会有特殊的显色反应，提供了一种荧光灵敏、肉眼可见、简便型检测铜离子的有效方法。配合物3~9的荧光性质主要来自于配体内电荷的转移。配合物1~9的荧光数据表明，配合物相对于H2L1配体的发射光谱略倾向于蓝移。对配合物1、2、3和10进行了荧光性质的理论计算。
采用4-[(8-羟基-5-喹啉)偶氮]-苯甲酸(H2L2)为配体，与金属Zn和Cd离子合成2个配合物：[Zn(L2)(H2O)2]n (11)和{[Cd(L2)(H2O)]·H2O}n (12)。配合物11为一维zig-zag链状结构，配合物12为二维层状结构，配合物11~12通过氢键和π-π堆积相互作用均连接形成了三维的超分子网络结构。讨论了配体的配位模式对所形成的配合物结构的影响。配合物11~12的热稳定性相对于配体H2L2具有明显的提高。配合物11~12的发射光谱相对于配体H2L2几乎没有发生改变，配合物的荧光性质主要来自于配体内的电荷转移。
采用偶氮苯-4,4'-二羧酸(H2L3)为配体，与金属Cd、Cu和Ag离子合成4种配合物：{[Cd2(L3)2(en)2]·DMF}n (13),[Cu(L3)(en)]n (14),{[Cu(L3)(phen)(H2O)]·DMA}n (15)和[Ag(L3)0.5]n (16)。配合物13~15为一维zig-zag链状结构，通过氢键和π-π堆积相互作用连接形成了三维的超分子网络结构，配合物16为三维结构。讨论了辅助配体乙二胺或1,10-邻菲罗啉对所形成的配合物结构的影响。配合物13~15的热稳定性相对于配体H2L3具有明显的提高。配合物13~15的发射光谱相对于配体H2L3均发生了较大红移，呈现蓝色荧光，荧光性质主要来自于配体对金属的电荷转移。
Azo compounds with good fluorescent properties have been attracting much attention in past decades. Due to their relatively low thermal stability, the application of azo compounds is limited. In this work, sixteen sorts of novel coordination polymers by solvothermal (hydrothermal) method have been prepared by reacting three types of azo-containing derivatives as the ligands with I/IIB metal ion. The structures of crystals were characterized by elemental analysis, single-crystal X-ray diffraction, infrared (IR) spectra and powder X-ray diffractions (PXRD). Thermal stability and fluorescent performance of coordination polymers were measured, calculated and analyzed. The synthetic conditions, the coordination model of ligand, hydrogen bonding and π-π stacking interactions were discussed to reveal the effects on azo coordination polymers applications in order to obtain stable azo compounds under high temperature. The emission spectra of coordination polymers move to the direction of visible light caused by the interaction of metals and ligands, which provides a wider application prospect for the practical application of azo compounds.
4-[(8-hydroxy-5-quinolinyl)azo]-benzenesulfonic acid (H2L1) as ligand reacts with Cu, Cd and Zn to synthesize ten sorts of novel coordination polymers:[Cu(L1)(en)]·0.5H2O (1),[Cu(L1)2][Cu(en)2]·2H2O (2),[Zn(L1)(H2O)4](3),{[Cd(L1)(en)]·EtOH}n (4),{[Cd(L1)(H2O)2]·H2O}n (5),{[Cd2(L1)2(en)2(H2O)2]·3H2O}n (6),{[Cd(L1)(en)]·DMF}n (7),[Zn3(L1)2(OH)2(H2O)6]n (8),[Zn(L1)(H2O)]n (9) and [Zn(M1)2](10). Compounds1,2,3and10exhibit zero-dimensional (0D) structure. Compounds4and5display infinite one-dimensional (1D) ladder-shaped chain structures. Compound6is1D zig-zag chain structure. Compounds7and8exhibit infinite1D double-metal chain structures. Compound9is a three-dimensional (3D) structure. Compounds1~8and10are further connected through hydrogen bonding and π-π interactions into3D supramolecular networks. The coordination model of ligand was discussed the effect of compound structure. From the description of the structure, the coordination model of sulfonate groups plays an important role in the structure of coordination compounds. Compound10was synthesized under the alkaline condition, which ligand was in situ reaction. The thermal stabilities of compounds1~9have an obvious enhancement with respect to H2L1ligand. The fluorescent properties of compounds1~2mainly come from the ligand-to-metal charge transfer, which have blue shift to H2L1ligand, showing violet fluorescence. The reaction between H2L1ligand and copper(II) ion leads to a sensitive fluorescent, visible to the naked eye and simple effective method of the detection of copper ion. The fluorescent properties of compounds3~9mainly come from the ligand-to-ligand charge transfer. The fluorescent data of compounds1~9indicate that the emission spectra of coordination compounds slightly inclined to blue shift to the H2L1ligand. The theoretical calculation of fluorescent spectra of compounds1,2,3and10were performed.
4-[(8-hydroxy-5-quinolinyl)azo]-benzoic acid (H2L2) as ligand reacts with Zn and Cd to synthesize two sorts of novel coordination polymers:[Zn(L2)(H2O)2]n (11) and {[Cd(L2)(H2O)]·H2O}n (12). Compound11exhibits1D zig-zag chain structure. Compound12is two-dimensional (2D) layer structure. Compounds11~12are further connected through hydrogen bonding and π-π interactions into3D supramolecular networks. The coordination model of ligand was studied to reveal the effect on compound structure. The thermal satbility properties of compounds11~12have an obvious enhancement to H2L2ligand. The emission spectra of compounds11~12have scarcely change to H2L2ligand. The fluorescent properties of compounds11~12mainly come from the charge transfer from ligand to ligand.
Azobenzene-4,4'-dicarboxylate (H2L3) as ligand reacts with Cd, Cu and Ag to synthesize four sorts of novel coordination polymers:{[Cd2(L3)2(en)2]·DMF}n (13),[Cu(L3)(en)]n (14),{[Cu(L3)(phen)(H2O)]·DMA}n (15) and [Ag(L3)0.5]n (16). Compounds13~15exhibit1D zig-zag chain structures, which are further connected through hydrogen bonding and π-π interactions into3D supramolecular networks. Compound16is3D structure. Ethylenediamine and1,10-phenanthroline as auxiliary ligands were studied to reveal the effect on compound structure. The thermal stability properties of compounds13~15have an obvious enhancement to H2L3ligand. The fluorescent properties of compounds13~15mainly come from the charge transfer from ligand to metal, which have red shift with respect to H2L3ligand, showing blue fluorescence.
引文
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