铕、铽高分子配合物和BODIPY类发光体系的研究
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摘要
本论文研究了两种不同类型的发光体系,主要包括铕、铽发光稀土高分子配合物的合成、表征以及发光性能的研究；线性乙烯基高分子配体在金属分离方面的应用；BODIPY类荧光染料的制备及其在阴离子识别中的研究。具体分为以下六个部分：
1.对稀土高分子配合物和BODIPY类荧光染料两种发光体系的研究进展及应用做了相应的文献综述。
2.合成了苯乙烯/丙烯酸共聚物(St/AA)配体(L1、L2、L3)和相应的稀土配合物(LnL13、LnL23、LnL33, Ln=Eu和Tb,结构式如图1),并对稀土高分子配合物的结构、性质、和发光性能进行了详细的研究。
3.用对氨基苯酚和8-氨基喹啉分别将苯乙烯/马来酸酐共聚物(SMA)开环,合成了高分子配体L4和Ls及相应的稀土配合物LnL43和LnL53(L4=PSMAAP; L5=PSMAAQ; Ln=Eu和Tb；图2和图3),并且对其结构和性质进行了表征,以及对配合物的发光性能作了详细的研究。
4.用苯乙烯/马来酸酐共聚物的水解产物来分离水溶液中的铅和锌,对配体SMA和Pb-SMA配合物(其结构如图4所示)进行了各种表征,并研究了SMA树脂对铅锌离子的吸附行为。
5.合成了以氨基香豆素为识别基团的BODIPY类阴离子荧光传感器1(图5),并且研究了其对阴离子的选择性。研究发现其对氟离子和磷酸二氢根离子具有很好的选择性,我们通过紫外吸收光谱、荧光光谱以及核磁滴定实验对其识别作用和识别机理进行了探讨。
6.研究了以苯胺为识别基团的BODIPY类阴离子荧光传感器2(图6),并探讨了它对氟离子的选择性识别作用和识别机理。
测定结果表明,所有合成的稀土高分子配合物组成固定,难溶于大多数有机溶剂,可用于制备稀土发光材料；高分子配体可以应用在金属的富集分离方面。BODIPY类荧光染料易溶于各种有机溶剂,荧光较强,带有不同识别基团的BODIPY类荧光染料可应用在离子识别方面。
The study of two kinds of fluorescent materials was carried out in this thesis, which mainly contains the synthesis, characterization and fluorescence properties of europium(Eu), terbium(Tb) macromolecular complexes, the application of linear polymeric vinyl ligands in the metal enrichment and separation, and the preparation and the application of sensing anions of BODIPY dyes. The paper consists of six parts as follows:
1. A brief review of the study progress and application of fluorescent lanthanides macromolecular complexes (LnMC) and BODIPY dyes has been given.
2. A series of poly styrene and acrylic acid ligands (L1, L2, L3) and corresponding lanthanides macromolecular complexes (LnL13, LnL23, LnL33, Ln=Eu and Tb, Fig.1) were synthesized, then the study of structure, characterization and fluorescence properties were carried out.
3. Copolymers of Poly(styrene-co-maleic anhydride) with8-Aminoquinoline (L4) and Poly(styrene-co-maleic anhydride) with p-aminophenolwith (L5) as well as their corresponding lanthanide macromolecular complexes LnL43and LnL53(Ln=Eu and Tb, Figs.2and3) were synthesized and characterized, and their fluorescence properties were studied detailed.
4. We use the copolymer of styrene-co-maleic anhydride to separate Pt2+and Zn2+in the solution, characterized SMA and Pb-SMA complexes, and the adsorption behavior of SMA towards Pb2+, Zn2+were also studied.
5. BODIPY derivative1(Fig.5) containing aminocoumarin as a recognition subunit was synthesized, and its selective recognition reaction and mechanism to F" and H2PO4-anions were studied.
6. The selective recognition and sensing of BODIPY derivative2(Fig.6) with phenylamine acting as a recognition subunit to fluoride anion were studied.
The results show that these synthesized lanthanide macromolecular complexes can be used to prepare fluorescent materials; the macromolecular guide can be used in the metal enrichment and separation. BODIPY fluorescence dye are easily soluble in most organic solvents, and they have strong fluorescence; some BODIPY dyes containing different recognition subunits can be applied to selectively recognize and sense different anions.
1.对稀土高分子配合物和BODIPY类荧光染料两种发光体系的研究进展及应用做了相应的文献综述。
2.合成了苯乙烯/丙烯酸共聚物(St/AA)配体(L1、L2、L3)和相应的稀土配合物(LnL13、LnL23、LnL33, Ln=Eu和Tb,结构式如图1),并对稀土高分子配合物的结构、性质、和发光性能进行了详细的研究。
3.用对氨基苯酚和8-氨基喹啉分别将苯乙烯/马来酸酐共聚物(SMA)开环,合成了高分子配体L4和Ls及相应的稀土配合物LnL43和LnL53(L4=PSMAAP; L5=PSMAAQ; Ln=Eu和Tb；图2和图3),并且对其结构和性质进行了表征,以及对配合物的发光性能作了详细的研究。
4.用苯乙烯/马来酸酐共聚物的水解产物来分离水溶液中的铅和锌,对配体SMA和Pb-SMA配合物(其结构如图4所示)进行了各种表征,并研究了SMA树脂对铅锌离子的吸附行为。
5.合成了以氨基香豆素为识别基团的BODIPY类阴离子荧光传感器1(图5),并且研究了其对阴离子的选择性。研究发现其对氟离子和磷酸二氢根离子具有很好的选择性,我们通过紫外吸收光谱、荧光光谱以及核磁滴定实验对其识别作用和识别机理进行了探讨。
6.研究了以苯胺为识别基团的BODIPY类阴离子荧光传感器2(图6),并探讨了它对氟离子的选择性识别作用和识别机理。
测定结果表明,所有合成的稀土高分子配合物组成固定,难溶于大多数有机溶剂,可用于制备稀土发光材料；高分子配体可以应用在金属的富集分离方面。BODIPY类荧光染料易溶于各种有机溶剂,荧光较强,带有不同识别基团的BODIPY类荧光染料可应用在离子识别方面。
The study of two kinds of fluorescent materials was carried out in this thesis, which mainly contains the synthesis, characterization and fluorescence properties of europium(Eu), terbium(Tb) macromolecular complexes, the application of linear polymeric vinyl ligands in the metal enrichment and separation, and the preparation and the application of sensing anions of BODIPY dyes. The paper consists of six parts as follows:
1. A brief review of the study progress and application of fluorescent lanthanides macromolecular complexes (LnMC) and BODIPY dyes has been given.
2. A series of poly styrene and acrylic acid ligands (L1, L2, L3) and corresponding lanthanides macromolecular complexes (LnL13, LnL23, LnL33, Ln=Eu and Tb, Fig.1) were synthesized, then the study of structure, characterization and fluorescence properties were carried out.
3. Copolymers of Poly(styrene-co-maleic anhydride) with8-Aminoquinoline (L4) and Poly(styrene-co-maleic anhydride) with p-aminophenolwith (L5) as well as their corresponding lanthanide macromolecular complexes LnL43and LnL53(Ln=Eu and Tb, Figs.2and3) were synthesized and characterized, and their fluorescence properties were studied detailed.
4. We use the copolymer of styrene-co-maleic anhydride to separate Pt2+and Zn2+in the solution, characterized SMA and Pb-SMA complexes, and the adsorption behavior of SMA towards Pb2+, Zn2+were also studied.
5. BODIPY derivative1(Fig.5) containing aminocoumarin as a recognition subunit was synthesized, and its selective recognition reaction and mechanism to F" and H2PO4-anions were studied.
6. The selective recognition and sensing of BODIPY derivative2(Fig.6) with phenylamine acting as a recognition subunit to fluoride anion were studied.
The results show that these synthesized lanthanide macromolecular complexes can be used to prepare fluorescent materials; the macromolecular guide can be used in the metal enrichment and separation. BODIPY fluorescence dye are easily soluble in most organic solvents, and they have strong fluorescence; some BODIPY dyes containing different recognition subunits can be applied to selectively recognize and sense different anions.
引文
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