CN103755633A - 8-aminoquinoline zinc perchlorate metal complex, and preparation method and application thereof - Google Patents
8-aminoquinoline zinc perchlorate metal complex, and preparation method and application thereof Download PDFInfo
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- -1 8-aminoquinoline zinc perchlorate metal complex Chemical class 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000013078 crystal Substances 0.000 claims abstract description 20
- 239000011701 zinc Substances 0.000 claims abstract description 18
- 229910020366 ClO 4 Inorganic materials 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 9
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
- 239000012065 filter cake Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 4
- 238000002447 crystallographic data Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 239000012454 non-polar solvent Substances 0.000 abstract 1
- 239000003446 ligand Substances 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 229910007541 Zn O Inorganic materials 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 1
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- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
- C30B29/54—Organic compounds
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- C30B7/00—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
- C30B7/14—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions the crystallising materials being formed by chemical reactions in the solution
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Abstract
本发明公开了8-氨基喹啉高氯酸锌金属配合物及其制备方法与应用。将Zn(ClO4)2和8-氨基喹啉分别溶于甲醇溶剂中。上述两种溶液混合,搅拌下回流,过滤,滤液在非极性溶剂中萃取,两星期后得到分子式为C18H16C12N4O8Zn的配合物单晶。该配合物通过氢键和π…π芳香环堆积构成三维超分子结构。荧光分光光度计测试表明该物质具有优良的荧光性能,可作为发光材料应用。The invention discloses an 8-aminoquinoline zinc perchlorate metal complex, a preparation method and an application thereof. Zn(ClO 4 ) 2 and 8-aminoquinoline were dissolved in methanol solvent, respectively. The above two solutions were mixed, refluxed under stirring, filtered, and the filtrate was extracted in a non-polar solvent, and a single crystal of the complex with the molecular formula C 18 H 16 C 12 N 4 O 8 Zn was obtained after two weeks. The complex forms a three-dimensional supramolecular structure through hydrogen bonding and π...π aromatic ring stacking. Fluorescence spectrophotometer tests show that the substance has excellent fluorescence properties and can be used as a luminescent material.
Description
技术领域 technical field
本发明属于有机合成领域,涉及一种8-氨基喹啉高氯酸锌金属配合物及其单晶以及制备方法,和该配合物作为发光材料方面的应用。 The invention belongs to the field of organic synthesis, and relates to an 8-aminoquinoline zinc perchlorate metal complex, a single crystal thereof, a preparation method, and an application of the complex as a luminescent material. the
背景技术 Background technique
金属有机配合物荧光材料在通讯、卫星、雷达、光学计算机、新型电池和生物分子探针等领域拥有潜在的应用价值,是分子材料家族的重要组成部分。这类功能性配合物的分子设计、合成及性质研究一直以来均受到广泛关注。由功能性分子构成的分子发光材料的发光性能很大程度上取决于配体与金属离子的配位状况。而芳香环与金属离子形成的螯合效应将极大增强材料发射荧光的效率。为此,选择8-氨基喹啉为有机配体与金属离子配位形成的金属有机配合物是该领域的优选材料。 Metal-organic complex fluorescent materials have potential application value in the fields of communication, satellite, radar, optical computer, new battery and biomolecular probe, and are an important part of the family of molecular materials. Molecular design, synthesis and property research of such functional complexes have been widely concerned. The luminescent properties of molecular luminescent materials composed of functional molecules largely depend on the coordination status of ligands and metal ions. The chelation effect formed by the aromatic ring and the metal ion will greatly enhance the efficiency of the material to emit fluorescence. For this reason, choosing 8-aminoquinoline as the metal-organic complex formed by the coordination of organic ligands and metal ions is the preferred material in this field. the
发明内容 Contents of the invention
本发明的第一个目的是提供一种8-氨基喹啉高氯酸锌金属配合物。该配合物通过氢键和π…π芳香环堆积构成三维超分子结构且具有优良的荧光性能,可作为潜在的发光材料应用。 The first object of the present invention is to provide a kind of 8-aminoquinoline zinc perchlorate metal complex. The complex forms a three-dimensional supramolecular structure through hydrogen bonding and π...π aromatic ring stacking and has excellent fluorescence properties, and can be used as a potential luminescent material. the
本发明所涉及的8-氨基喹啉高氯酸锌金属配合物的化学式为(L1)2·Zn(ClO4)2,其中L1为8-氨基喹啉。 The chemical formula of the 8-aminoquinoline zinc perchlorate metal complex involved in the present invention is (L 1 ) 2 ·Zn(ClO 4 ) 2 , wherein L 1 is 8-aminoquinoline.
本发明的第二个目的是提供一种8-氨基喹啉高氯酸锌金属配合物的制备方法。 Second object of the present invention is to provide a kind of preparation method of 8-aminoquinoline zinc perchlorate metal complex. the
为达到上述目的,本发明8-氨基喹啉高氯酸锌金属配合物的制备方法是:以Zn(ClO4)2与L1的摩尔比为1∶2计,将Zn(ClO4)2和L1均溶于甲醇溶剂中,搅拌下回流;过滤,滤液在非极性萃取溶剂中萃取,两星期后得到无色晶体,过滤,乙醚洗涤滤饼,得目标配合物;所述的L1为8-氨基喹啉。 In order to achieve the above object, the preparation method of the 8-aminoquinoline zinc perchlorate metal complex of the present invention is: the molar ratio of Zn(ClO 4 ) 2 and L 1 is 1:2, Zn(ClO 4 ) 2 and L1 were all dissolved in methanol solvent, and refluxed under stirring; filtered, the filtrate was extracted in a non-polar extraction solvent, and colorless crystals were obtained after two weeks, filtered, and the filter cake was washed with ether to obtain the target complex; the L 1 is 8-aminoquinoline.
所述的搅拌下回流的时间为2~6小时。 The time for reflux under stirring is 2 to 6 hours. the
所述的萃取溶剂为乙醚或四氯化碳。 The extraction solvent is diethyl ether or carbon tetrachloride. the
本发明选择高氯酸锌为构筑单元,以能形成氢键的8-氨基喹啉作为二齿配体,进行自组装,得到具有三维超分子结构和荧光性的金属-有机配合物单晶。它们的二级结构单元为:晶体属于三斜晶系,空间群为P-1,晶胞参数为: α=74.9950(10)°,β=77.4690(10)°,γ=70.8460(10)°。该配合物的不对称单元中含1个Zn2+,2个L1配体和2个ClO4 -。每个Zn2+与来自于两个L1配体的4个N原子和来自于两个ClO4 -的2个O原子配位,形成扭曲的八面体配位几何构型。分子间弱的氢键和π…π芳香环堆积构成三维超分子结构。其中,八面体的Zn-N键长为Zn-O键长为 In the invention, zinc perchlorate is selected as a building unit, and 8-aminoquinoline capable of forming hydrogen bonds is used as a bidentate ligand for self-assembly to obtain a metal-organic complex single crystal with a three-dimensional supramolecular structure and fluorescence. Their secondary structural units are: the crystal belongs to the triclinic system, the space group is P-1, and the unit cell parameters are: α=74.9950(10)°, β=77.4690(10)°, γ=70.8460(10)°. The asymmetric unit of the complex contains 1 Zn 2+ , 2 L 1 ligands and 2 ClO 4 - . Each Zn 2+ is coordinated with 4 N atoms from two L 1 ligands and 2 O atoms from two ClO 4 - , forming a distorted octahedral coordination geometry. The weak intermolecular hydrogen bonds and π…π aromatic ring stacking form a three-dimensional supramolecular structure. Among them, the Zn-N bond length of octahedron is Zn-O bond length is
N-Zn-N键角数值分别为81.03(7)°、98.97(7)°和180.0°。O-Zn-O键角数值为180.00(8)°。本发明制备方法简单,原料易得,且该配合物具有三维超分子结构。 The values of N-Zn-N bond angles are 81.03(7)°, 98.97(7)° and 180.0°, respectively. The value of O-Zn-O bond angle is 180.00(8)°. The preparation method of the invention is simple, the raw materials are easy to obtain, and the complex has a three-dimensional supramolecular structure. the
本发明的第三个目的是提供一种8-氨基喹啉高氯酸锌金属配合物作为发光材料方面的应用。 The third object of the present invention is to provide a kind of 8-aminoquinoline zinc perchlorate metal complex as a luminescent material. the
附图说明 Description of drawings
图1是本发明8-氨基喹啉高氯酸锌金属配合物的晶体结构图; Fig. 1 is the crystal structure figure of 8-aminoquinoline zinc perchlorate metal complex of the present invention;
图2是本发明8-氨基喹啉高氯酸锌金属配合物的堆积结构图; Fig. 2 is the packing structure figure of 8-aminoquinoline zinc perchlorate metal complex of the present invention;
图3是本发明8-氨基喹啉高氯酸锌金属配合物的固体荧光光谱图。 Fig. 3 is the solid fluorescence spectrogram of the 8-aminoquinoline zinc perchlorate metal complex of the present invention. the
具体实施方式 Detailed ways
本发明8-氨基喹啉高氯酸锌金属配合物的化学式为(L1)2·Zn(ClO4)2,其中的L1为8-氨基喹啉。 The chemical formula of the 8-aminoquinoline zinc perchlorate metal complex of the present invention is (L 1 ) 2 ·Zn(ClO 4 ) 2 , wherein L 1 is 8-aminoquinoline.
下面结合具体实施实例进一步阐述本发明。 The present invention will be further described below in conjunction with specific implementation examples. the
实施例1:0.05mmol Zn(ClO4)2(13.2mg)和0.10mmol L1(14.4mg)分别溶于10ml甲醇溶剂中,室温条件下将两种溶液相混合,搅拌下回流2小时,过滤,滤液置于50ml烧杯中,用薄膜封口,并扎小孔,放在乙醚池中萃取。两星期后得到无色晶体,过滤,滤饼用乙醚洗涤,得目标配合物,基于Zn(ClO4)2计算的产率为51%。 Example 1: 0.05mmol Zn(ClO 4 ) 2 (13.2mg) and 0.10mmol L 1 (14.4mg) were respectively dissolved in 10ml of methanol solvent, and the two solutions were mixed at room temperature, refluxed for 2 hours under stirring, and filtered , the filtrate was placed in a 50ml beaker, sealed with a film, and a small hole was pierced, and extracted in an ether pool. After two weeks, colorless crystals were obtained, which were filtered and the filter cake was washed with ether to obtain the target complex with a yield of 51% based on Zn(ClO 4 ) 2 .
实施例2:0.05mmol Zn(ClO4)2(13.2mg)和0.10mmol L1(14.4mg)分别溶于10ml甲醇溶剂中,室温条件下将两种溶液相混合,搅拌下回流4小时,过滤,滤液置于50ml烧杯中,用薄膜封口,并扎小孔,放在乙醚池中萃取。两星期后得到无色晶体,过滤,滤饼用乙醚洗涤,得目标配合物,基于Zn(ClO4)2计算的产率为67%。 Example 2: 0.05mmol Zn(ClO 4 ) 2 (13.2mg) and 0.10mmol L 1 (14.4mg) were respectively dissolved in 10ml of methanol solvent, and the two solutions were mixed at room temperature, refluxed for 4 hours under stirring, and filtered , the filtrate was placed in a 50ml beaker, sealed with a film, and a small hole was pierced, and extracted in an ether pool. After two weeks, colorless crystals were obtained, which were filtered and the filter cake was washed with ether to obtain the target complex with a yield of 67% based on Zn(ClO 4 ) 2 .
实施例3:0.05mmol Zn(ClO4)2(13.2mg)和0.10mmol L1(14.4mg)分别溶于10ml甲醇溶剂中,室温条件下将两种溶液相混合,搅拌下回流4小时,过滤,滤液置于50ml烧杯中,用薄膜封口,并扎小孔,放在四氯化碳池中萃取。两星期后得到无色晶体,过滤,滤饼用乙醚洗涤,得目标配合物,基于Zn(ClO4)2计算的产率为35%。 Example 3: 0.05mmol Zn(ClO 4 ) 2 (13.2mg) and 0.10mmol L 1 (14.4mg) were respectively dissolved in 10ml of methanol solvent, and the two solutions were mixed at room temperature, refluxed for 4 hours under stirring, and filtered , the filtrate was placed in a 50ml beaker, sealed with a film, and a small hole was pierced, and extracted in a carbon tetrachloride pool. Two weeks later, colorless crystals were obtained, which were filtered, and the filter cake was washed with ether to obtain the target complex with a yield of 35% based on Zn(ClO 4 ) 2 .
实施例4:0.05mmol Zn(ClO4)2(13.2mg)和0.10mmol L1(14.4mg)分别溶于10ml甲醇溶剂中,室温条件下将两种溶液相混合,搅拌下回流6小时,过滤,滤液置于50ml烧杯中,用薄膜封口,并扎小孔,放在四氯化碳池中萃取。两星期后得到无色晶体,过滤,滤饼用乙醚洗涤,得目标配合物,基于Zn(ClO4)2计算的产率为54%。 Example 4: 0.05mmol Zn(ClO 4 ) 2 (13.2mg) and 0.10mmol L 1 (14.4mg) were respectively dissolved in 10ml of methanol solvent, and the two solutions were mixed at room temperature, refluxed for 6 hours under stirring, and filtered , the filtrate was placed in a 50ml beaker, sealed with a film, and a small hole was pierced, and extracted in a carbon tetrachloride pool. Two weeks later, colorless crystals were obtained, which were filtered, and the filter cake was washed with ether to obtain the target complex with a yield of 54% based on Zn(ClO 4 ) 2 .
实施例5:发光材料,具体的方法步骤如下: Embodiment 5: luminescent material, concrete method step is as follows:
通过荧光分光光度计,分别进行8-氨基喹啉高氯酸锌金属配合物的激发波长和发射波长 的扫描,选择并确定最佳波长。 The excitation wavelength and emission wavelength of the 8-aminoquinoline zinc perchlorate metal complex were scanned respectively by a fluorescence spectrophotometer, and the optimal wavelength was selected and determined. the
结论:该配合物的激发波长和发射波长分别为340.0nm和521.8nm。 Conclusion: The excitation and emission wavelengths of the complex are 340.0nm and 521.8nm, respectively. the
本发明8-氨基喹啉高氯酸锌金属配合物的结构测定: The structural determination of 8-aminoquinoline zinc perchlorate metal complex of the present invention:
晶体结构采用Bruker Smart Apex II CCD单晶衍射仪测定,以石墨单色化的Mokα射线( 为入射辐射,ω-2θ扫描方式收集室温X-射线单晶衍射数据,最小二乘法精修晶胞参数,SHELXL-97直接法解得晶体结构,全矩阵最小平方二乘法对所有非氢原子位置及各向异性热温度因子进行精修。所有的H原子位置由几何加氢方式确定。详细的晶体测定数据见表1,结构见图1和2,荧光光谱见图3。 The crystal structure was determined using a Bruker Smart Apex II CCD single crystal diffractometer, and Mokα rays monochromated with graphite ( For the incident radiation, the ω-2θ scanning method collects X-ray single crystal diffraction data at room temperature, the least squares method refines the unit cell parameters, the SHELXL-97 direct method solves the crystal structure, and the full matrix least squares method calculates all non-hydrogen atom positions and anisotropic thermal temperature factor for refinement. All H atom positions are determined by geometric hydrogenation. The detailed crystal determination data is shown in Table 1, the structure is shown in Figures 1 and 2, and the fluorescence spectrum is shown in Figure 3.
表1本发明8-氨基喹啉高氯酸锌金属配合物的晶体学数据 The crystallographic data of table 1 8-aminoquinoline zinc perchlorate metal complex of the present invention
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