稀土铕、铽有机配合物的制备与性能研究
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摘要
稀土有机配合物兼具稀土离子发光效率高、色纯度高和有机配体所需激发能量低、吸收效率高、分子结构可调的优点,在光致发光、电致发光等领域具有潜在的应用价值。因此,本文通过对有机分子的设计和裁剪,依据能级匹配原则、分子内能量传递机制,合成了四种β-二酮配体和两种芳香羧酸配体及其稀土铕、铽配合物。通过元素分析、红外光谱、紫外-可见光谱、磷光光谱、荧光光谱等对配体及配合物进行了表征,并筛选出发光性能较好的配合物,进一步研究了其荧光性能。主要工作如下：
首先,采用经典克莱森缩合反应合成了四种β-二酮配体(L1-L4)：1-(4-溴苯)-3-苯基丙烷-1,3-二酮、1-(4-溴苯)-4,4,4-三氟丁烷-1,3-二酮、1-(4-氨基苯)-3-苯基丙烷-1,3-二酮、1-(4-氨基苯)-4,4.4-三氟丁烷-1,3-二酮。以β-二酮为第一配体,邻菲罗啉(phen)为第二配体,合成出新型稀土铕、铽二元和三元配合物,其组成分别为RE(Ln)3·2H20和RE(Ln)3phen(RE=Eu.Tb;n=1-4)。主要研究了配合物的光物理性质,结果表明：第一配体的最低三重态能级为影响稀土配合物发光性能的主要因素,第二配体phen在不同的配合物中可以起到协同配位和能量传递的作用。针对不同的发光现象,分别从Antenna效应、配体结构及配位能力、Dexter电子交换机制、热失活机制等方面给予了解释。
其次,合成了两种芳香羧酸配体：2-二苯胺羰基苯甲酸(L5)、2-苯胺羰基苯甲酸(L6)。以芳香羧酸为第一配体,咪唑并[5,6-f]邻菲罗啉(IP)为第二配体,合成出新型稀土铕、铽三元配合物RE(Ln)3IP(RE=Eu,Tb;n=5,6)。主要研究了配合物的发光性质,结果显示铕、铽配合物均表现出稀土离子的特征发射,当第一配体的结构发生变化时,配合物的发光强度发生了明显的变化,这是由于2-二苯胺羰基苯甲酸中的氮原子上增加一个苯环后,改变了体系中电子云的分布情况,导致配体π-π*跃迁吸收的能量不能有效的通过Antenna效应传递给稀土中心离子,进而影响了配合物的发光强度。
最后,在两类稀土配合物中选择出发光强度大、单色性好的稀土配合物,进一步研究了其荧光性能,结果显示,配合物的荧光量子效率和荧光寿命与发光强度成正比,铕的β-二酮类配合物和铽的芳香羧酸类配合物荧光性能较好。
Rare earth organic complexes demonstrate potential applications in photoluminescence and electroluminescence due to their high quantum efficiency, sharp emission bands, low excitation energy, high absorption and adjustable molecular structure. So, in this paper, according to the design and cutting of organic molecules, the level matching principle and intramolecular energy transfer mechanism, four β-diketonate ligands and two aromatic carboxylic acid ligands and their Eu, Tb complexes were synthesized. The ligands and the complexes were characterized by elemental analysis, IR spectroscopy, UV-visible spectroscopy. phosphorescence spectra and fluorescence spectra. Furthermore, the complexes with better fluorescent properties were studied.The main works were as follows:
Firstly, the novel β-diketone ligands1-(4-bromophenyl)-3-phenylpropane-1,3-dione,1-(4-bromophenyl)-4,4.4-trifluorobutane-1,3-dione,1-(4-aminophenyl)-3-phenylpropane-1,3-dion and1-(4-aminophenyl)-4,4.4-trifluorobutane-1,3-dione were synthesized at room temperature by classical Claisen condensation reaction. With the P-diketone as the first ligand and phen as the secondary ligand, rare-earth Eu, Tb binary and ternary complexes was prepared. The compositions of the complexes were RE(Ln)3·2H2O and RE(Ln)3phen(RE=Eu.Tb;n=1-4). The experimental results indicated that the luminescent properties of the complexes were mainly affected by the lowest triplet state energy of the first ligand. and the second ligand phen acted as the synergistic coordination or energy translater in different complexes. Moreover, the different luminous phenomena was explained by antenna effect, structure and coordinated ability of ligand. Dexter's resonant exchange interaction theory and thermal deactivation mechanism.
Secondly, the aromatic carboxylic acid ligands were synthesized at room temperature. With2-diphenylamine carbonyl benzoic acid and2-aniline carbonyl benzoic acid as the first ligand and imidazo[5.6-f] phenanthroline(IP) as the secondary ligand, new rare-earth Eu and Tb ternary complexes were prepared. The compositions of the complexes were RE(Ln)3phen(RE=Eu,Tb;n=5,6). Fluorescence spectra demonstrated that two kinds of ternary organic complexes could emit characteristic fluorescence of rare earth ions.The fluorescence intensities of two complexes were found to be influenced with the molecule structure, the benzene ring which was coordinated with nitrogen atom increased in2-diphenylamine carbonyl benzoic acid. In the system of ternary complexes, due to the different coordinated number of benzene ring, the mobility of electron and the distribution of electron cloud were changed. The variation affected the transition of the π electrons, which can absorb the energy in ternary complexes. So, the energy transfer efficiency from the first ligand to rare earth ions decreased and Antenna effect achieved inefficiency in the complexes.
Finally, the rare earth complexes with stronger luminous intensity and better monochromaticity were choosen and their fluorescence properties were further characterized. The results showed that the fluorescence quantum efficiency and life time were congruously changed with luminous intensity, and the fluorescence properties of europium complexes with β-diketone and terbium complexes with aromatic carboxylic acid were better.
首先,采用经典克莱森缩合反应合成了四种β-二酮配体(L1-L4)：1-(4-溴苯)-3-苯基丙烷-1,3-二酮、1-(4-溴苯)-4,4,4-三氟丁烷-1,3-二酮、1-(4-氨基苯)-3-苯基丙烷-1,3-二酮、1-(4-氨基苯)-4,4.4-三氟丁烷-1,3-二酮。以β-二酮为第一配体,邻菲罗啉(phen)为第二配体,合成出新型稀土铕、铽二元和三元配合物,其组成分别为RE(Ln)3·2H20和RE(Ln)3phen(RE=Eu.Tb;n=1-4)。主要研究了配合物的光物理性质,结果表明：第一配体的最低三重态能级为影响稀土配合物发光性能的主要因素,第二配体phen在不同的配合物中可以起到协同配位和能量传递的作用。针对不同的发光现象,分别从Antenna效应、配体结构及配位能力、Dexter电子交换机制、热失活机制等方面给予了解释。
其次,合成了两种芳香羧酸配体：2-二苯胺羰基苯甲酸(L5)、2-苯胺羰基苯甲酸(L6)。以芳香羧酸为第一配体,咪唑并[5,6-f]邻菲罗啉(IP)为第二配体,合成出新型稀土铕、铽三元配合物RE(Ln)3IP(RE=Eu,Tb;n=5,6)。主要研究了配合物的发光性质,结果显示铕、铽配合物均表现出稀土离子的特征发射,当第一配体的结构发生变化时,配合物的发光强度发生了明显的变化,这是由于2-二苯胺羰基苯甲酸中的氮原子上增加一个苯环后,改变了体系中电子云的分布情况,导致配体π-π*跃迁吸收的能量不能有效的通过Antenna效应传递给稀土中心离子,进而影响了配合物的发光强度。
最后,在两类稀土配合物中选择出发光强度大、单色性好的稀土配合物,进一步研究了其荧光性能,结果显示,配合物的荧光量子效率和荧光寿命与发光强度成正比,铕的β-二酮类配合物和铽的芳香羧酸类配合物荧光性能较好。
Rare earth organic complexes demonstrate potential applications in photoluminescence and electroluminescence due to their high quantum efficiency, sharp emission bands, low excitation energy, high absorption and adjustable molecular structure. So, in this paper, according to the design and cutting of organic molecules, the level matching principle and intramolecular energy transfer mechanism, four β-diketonate ligands and two aromatic carboxylic acid ligands and their Eu, Tb complexes were synthesized. The ligands and the complexes were characterized by elemental analysis, IR spectroscopy, UV-visible spectroscopy. phosphorescence spectra and fluorescence spectra. Furthermore, the complexes with better fluorescent properties were studied.The main works were as follows:
Firstly, the novel β-diketone ligands1-(4-bromophenyl)-3-phenylpropane-1,3-dione,1-(4-bromophenyl)-4,4.4-trifluorobutane-1,3-dione,1-(4-aminophenyl)-3-phenylpropane-1,3-dion and1-(4-aminophenyl)-4,4.4-trifluorobutane-1,3-dione were synthesized at room temperature by classical Claisen condensation reaction. With the P-diketone as the first ligand and phen as the secondary ligand, rare-earth Eu, Tb binary and ternary complexes was prepared. The compositions of the complexes were RE(Ln)3·2H2O and RE(Ln)3phen(RE=Eu.Tb;n=1-4). The experimental results indicated that the luminescent properties of the complexes were mainly affected by the lowest triplet state energy of the first ligand. and the second ligand phen acted as the synergistic coordination or energy translater in different complexes. Moreover, the different luminous phenomena was explained by antenna effect, structure and coordinated ability of ligand. Dexter's resonant exchange interaction theory and thermal deactivation mechanism.
Secondly, the aromatic carboxylic acid ligands were synthesized at room temperature. With2-diphenylamine carbonyl benzoic acid and2-aniline carbonyl benzoic acid as the first ligand and imidazo[5.6-f] phenanthroline(IP) as the secondary ligand, new rare-earth Eu and Tb ternary complexes were prepared. The compositions of the complexes were RE(Ln)3phen(RE=Eu,Tb;n=5,6). Fluorescence spectra demonstrated that two kinds of ternary organic complexes could emit characteristic fluorescence of rare earth ions.The fluorescence intensities of two complexes were found to be influenced with the molecule structure, the benzene ring which was coordinated with nitrogen atom increased in2-diphenylamine carbonyl benzoic acid. In the system of ternary complexes, due to the different coordinated number of benzene ring, the mobility of electron and the distribution of electron cloud were changed. The variation affected the transition of the π electrons, which can absorb the energy in ternary complexes. So, the energy transfer efficiency from the first ligand to rare earth ions decreased and Antenna effect achieved inefficiency in the complexes.
Finally, the rare earth complexes with stronger luminous intensity and better monochromaticity were choosen and their fluorescence properties were further characterized. The results showed that the fluorescence quantum efficiency and life time were congruously changed with luminous intensity, and the fluorescence properties of europium complexes with β-diketone and terbium complexes with aromatic carboxylic acid were better.
引文
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