氮杂冠醚、氮支套索冠醚及其金属配合物的合成与表征
摘要
稀土大环化合物具有独特的结构和性质，在新材料的研究、稀土的分析及分离等方面有潜在的应用。为了进一步研究和探讨不同类型的大环配体氮原子上取代基对荧光性质的影响等，本论文报道了八个氮杂冠醚氮取代衍生物即氮支套索冠醚的合成(L~1：1,22-二乙酰1,22-二氮杂-3,6:17,20-二苯-7,10,13,16,25-五氧杂环二十七烷，L~2：1,22-二苯甲酰-1,22-二氮杂-3,6:17,20-二苯-7,10,13,16,25-五氧杂环二十七烷，L~3：1,22-二(2-羧基-苯甲酰)-1,22-二氮杂-3,6:17,20-二苯-7,10,13,16,25-五氧杂环二十七烷，L~4：1,22-二(4-羧基-丁酰)-1,22-二氮杂-3,6:17,20-二苯-7,10,13,16,25-五氧杂环二十七烷，L~5：1,22,25-三乙酰-1,22,25-三氮杂-3,6:17,20-二苯-7,10,13,16-四氧杂环二十七烷，L~6：1,22,25-三苯甲酰-1,22,25-三氮杂-3,6:17,20-二苯-7,10,13,16-四氧杂环二十七烷，L~7：1,22,25-三(2-羧基-苯甲酰)-1,22,25-三氮杂-3,6:17,20-二苯-7,10,13,16-四氧杂环二十七烷，L~8：1,22,25-三(4-羧基-丁酰)-1,22,25-三氮杂-3,6:17,20-二苯-7,10,13,16-四氧杂环二十七烷)及其稀土硝酸盐配合物的合成，通过元素分析、摩尔电导、红外光谱及热分析等测试手段研究了它们的组成及性质。
结果发现，八个氮支套索冠醚配体与稀土离子均有较好的配位作用。由于羰基的引入，降低了环上氮原子上的电子云密度，并引起环空间构型的改变，使得环上的氮原子均未参与配位，而只有醚氧和羰基氧原子参与了配位。
配合物的荧光光谱研究结果表明，Eu(Ⅲ)和Tb(Ⅲ)与所有配体形成的配合物均有不同强度的荧光，其中以L~6配合物荧光最强；同时，我们通过对配体三重态能级的测定，研究了它们的稀土硝酸盐配合物荧光性质变化的规律。
喹啉及其衍生物的配合物在电致发光方面的应用也是当今新材料研究的一大热点，但将喹啉基团引入冠醚环体系的研究还未有报道。有鉴于此，我们设计合成了两个含喹啉基团的冠醚配体(L~9：1,22-二氮杂-3,6:17,20-二喹啉-7,10,13,16,25-五氧杂-环二十七烷，L~(10)：1,22,25-三氮杂-3,6:17,20-二喹啉-7,10,13,16-四氧杂-环二十七烷)及其铝、锌硝酸盐的配合物，通过元素分析、摩尔电导、红外光谱及荧光分析等测试手段研究了它们的组成及性质。
结果发现，由于冠醚环的吸电子作用，使得喹啉基团主控的HOMO-LUMO能级差别变小，使得喹啉基团在中心离子激发下的荧光发射波长向长波方向移动，即发射峰红移。
The coordination complexes of rare earth with macro cyclic ligand have distinctive structure and properties, and potential application in exploring new materials, the investigation of analysis and separation of the ions. In order to investigate the coordinating properties of different macro cyclic ligand with rare earth ions, and the influence of substituent group of the ligand to their rare earth complexes' fluorescence properties, this paper reports the synthesis of eight nitrogen-pivot benzo-aza-lariat crown ethers (L~1:1,22-diacetyl-1,22-diaza-3,6:14,17-dibenzo-7,10,13,16,25-pentaoxa-cyclotetracosane; L~2:1,22-dibenzoyl-1,22-diaza-3,6:14,17-dibenzo-7,10,13,16,25-pentaoxa-cyclotetracosane;L~3:1,22-di(2-carboxyl-benzoyl)-1,22-diaza-3,6:14,17-dibenzo-7,10, 13,16,25-pentaoxa-cyclotetracosane; L~4:1,22-di(3-carboxyl-propionyl)-1,22-diaza-3,6:14,17-dibenzo-7,10,13,16,25-pentaoxa-cyclotetracosane; L~5:1,22,25-triacetyl-1,22,25-triaza-3,6:17,20-dibenzo-7,10,13,16-tetraoxa-cycloheptacosane; L~6:1,22,25-tribenzoyl-1,22,25-triiaza-3,6:14,17-dibenzo-7,10,13,16-tetraoxa-cyclotetracosane;L~7:1,22,25-tri(2-carboxyl-benzoyl)-1,22,25-triaza-3,6:14,17-dibenzo-7,10,13,16-tetraoxa-cyclote-tracosane;L~8:1,22,25-tri(3-carboxyl-propionyl)-1, 22,25-triaza-3,6:14,17-dibenzo-7,10,13,16-tetraoxa-cyclotetracosane ) and their rare earth complexes through elemental analysis, molar conductance, IR spectra and thermo gravimetric analysis.
From the data we get, it can be seen that all nitrogen-pivot benzo-aza-lariat crown ether ligands have good coordinating properties with rare earth ions. For the installed acyl in the ring, which decrease electronic cloudy density around nitrogen atoms, and it also change the spatial structure of ligand, thus nitrogen atoms not take part in coordinate with rare earth ions, and only stop oxygen and oxygen atoms in the acyl act as donator atoms.
The data of fluorescence spectra indicates that complexes of these ligands with Eu (III), Tb (III) all show characteristic line emission of rare earth ions. The complexes of L6 show higher luminescence intensity than others. At the same time, we determine the triplet state of the ligands, study the rule that control the change of their fluorescence properties in a deep step.
The complexes of quinolin and its derivates have recently received considerable attention due to their potential applications in electroluminescence (EL). But compounds of the crown ethers contain quinolyl have not been reported. For this reason, we design and synthesize two novel quino-aza-crown ethers: L~9:1, 22-diaza-3,6:17,20-diquino-7,10,13,16,25-pentaoxa-cyclotetra-cos-ane,L~(10):1,22,25-triaza-3,6:17,20-diquino-7,10,13,16-tetraoxa-cyclotetracosane.Thecomplexe s of Zn(II) and Al(III) of L~9 and L~(10) are synthesized too. The ligands and complexes are characterized by elemental analysis, molar conductance, and IR spectra analysis. The data of fluorescence spectra indicates thatλ_(em) of the complexes of the novel quino-aza-crown ethers are red shift. It can be attributed to the electron absorbing of crown ring makes the HOMO-LUMO energy gap decreasing.
结果发现，八个氮支套索冠醚配体与稀土离子均有较好的配位作用。由于羰基的引入，降低了环上氮原子上的电子云密度，并引起环空间构型的改变，使得环上的氮原子均未参与配位，而只有醚氧和羰基氧原子参与了配位。
配合物的荧光光谱研究结果表明，Eu(Ⅲ)和Tb(Ⅲ)与所有配体形成的配合物均有不同强度的荧光，其中以L~6配合物荧光最强；同时，我们通过对配体三重态能级的测定，研究了它们的稀土硝酸盐配合物荧光性质变化的规律。
喹啉及其衍生物的配合物在电致发光方面的应用也是当今新材料研究的一大热点，但将喹啉基团引入冠醚环体系的研究还未有报道。有鉴于此，我们设计合成了两个含喹啉基团的冠醚配体(L~9：1,22-二氮杂-3,6:17,20-二喹啉-7,10,13,16,25-五氧杂-环二十七烷，L~(10)：1,22,25-三氮杂-3,6:17,20-二喹啉-7,10,13,16-四氧杂-环二十七烷)及其铝、锌硝酸盐的配合物，通过元素分析、摩尔电导、红外光谱及荧光分析等测试手段研究了它们的组成及性质。
结果发现，由于冠醚环的吸电子作用，使得喹啉基团主控的HOMO-LUMO能级差别变小，使得喹啉基团在中心离子激发下的荧光发射波长向长波方向移动，即发射峰红移。
The coordination complexes of rare earth with macro cyclic ligand have distinctive structure and properties, and potential application in exploring new materials, the investigation of analysis and separation of the ions. In order to investigate the coordinating properties of different macro cyclic ligand with rare earth ions, and the influence of substituent group of the ligand to their rare earth complexes' fluorescence properties, this paper reports the synthesis of eight nitrogen-pivot benzo-aza-lariat crown ethers (L~1:1,22-diacetyl-1,22-diaza-3,6:14,17-dibenzo-7,10,13,16,25-pentaoxa-cyclotetracosane; L~2:1,22-dibenzoyl-1,22-diaza-3,6:14,17-dibenzo-7,10,13,16,25-pentaoxa-cyclotetracosane;L~3:1,22-di(2-carboxyl-benzoyl)-1,22-diaza-3,6:14,17-dibenzo-7,10, 13,16,25-pentaoxa-cyclotetracosane; L~4:1,22-di(3-carboxyl-propionyl)-1,22-diaza-3,6:14,17-dibenzo-7,10,13,16,25-pentaoxa-cyclotetracosane; L~5:1,22,25-triacetyl-1,22,25-triaza-3,6:17,20-dibenzo-7,10,13,16-tetraoxa-cycloheptacosane; L~6:1,22,25-tribenzoyl-1,22,25-triiaza-3,6:14,17-dibenzo-7,10,13,16-tetraoxa-cyclotetracosane;L~7:1,22,25-tri(2-carboxyl-benzoyl)-1,22,25-triaza-3,6:14,17-dibenzo-7,10,13,16-tetraoxa-cyclote-tracosane;L~8:1,22,25-tri(3-carboxyl-propionyl)-1, 22,25-triaza-3,6:14,17-dibenzo-7,10,13,16-tetraoxa-cyclotetracosane ) and their rare earth complexes through elemental analysis, molar conductance, IR spectra and thermo gravimetric analysis.
From the data we get, it can be seen that all nitrogen-pivot benzo-aza-lariat crown ether ligands have good coordinating properties with rare earth ions. For the installed acyl in the ring, which decrease electronic cloudy density around nitrogen atoms, and it also change the spatial structure of ligand, thus nitrogen atoms not take part in coordinate with rare earth ions, and only stop oxygen and oxygen atoms in the acyl act as donator atoms.
The data of fluorescence spectra indicates that complexes of these ligands with Eu (III), Tb (III) all show characteristic line emission of rare earth ions. The complexes of L6 show higher luminescence intensity than others. At the same time, we determine the triplet state of the ligands, study the rule that control the change of their fluorescence properties in a deep step.
The complexes of quinolin and its derivates have recently received considerable attention due to their potential applications in electroluminescence (EL). But compounds of the crown ethers contain quinolyl have not been reported. For this reason, we design and synthesize two novel quino-aza-crown ethers: L~9:1, 22-diaza-3,6:17,20-diquino-7,10,13,16,25-pentaoxa-cyclotetra-cos-ane,L~(10):1,22,25-triaza-3,6:17,20-diquino-7,10,13,16-tetraoxa-cyclotetracosane.Thecomplexe s of Zn(II) and Al(III) of L~9 and L~(10) are synthesized too. The ligands and complexes are characterized by elemental analysis, molar conductance, and IR spectra analysis. The data of fluorescence spectra indicates thatλ_(em) of the complexes of the novel quino-aza-crown ethers are red shift. It can be attributed to the electron absorbing of crown ring makes the HOMO-LUMO energy gap decreasing.
引文
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