带臂大环类配体稀土配合物及其荧光化学传感器的研究
摘要
稀土离子具有独特的电子结构和成键特征，使得稀土化合物表现出独特的发光性能，功能性稀土发光配合物的设计、组装也因而成为一个富有挑战性的课题。众多在功能超分子化学中表现出潜在应用前景的有机配体中，酰胺型配体在制备具有优良荧光性质的稀土配合物中表现尤其引人注目。此类配体具有合成简单、结构可调和共轭敏化基团可换等优点。通过调整配体的功能基团可以实现配合物优良的荧光性质，另外还可以通过选择不同的功能性配体骨架及端基，以实现人们对配体和配合物特殊性质的需要。带臂大环类配体稀土配合物因为含有大环结构而具有潜在的分子识别能力。为了进一步研究和探讨带臂大环类配体对稀土离子的配位选择性、配体骨架结构、功能末端基和抗衡阴离子对配合物荧光性质的影响，以及其稀土发光配合物的荧光传感性质，本论文报道了八种酰胺型带臂大环配体L~Ⅰ～L~Ⅷ、四种其它类型的带臂大环配体L~Ⅸ～L~Ⅶ及其稀土超分子配合物的合成与表征，并对配合物的结构和荧光性质进行了系统研究。另外，本论文对配体L~Ⅰ、L~Ⅱ和L~Ⅷ硝酸铽配合物的阳离子荧光传感识别进行了研究，对L~Ⅵ硝酸铽配合物的溶剂分子识别进行了研究。
本论文共分五章：
第一章：简要综述了近年来稀土发光配合物和荧光化学传感器的研究进展。
第二章：以五种不同种类水杨酰胺为功能末端基设计合成出以苯并-15-冠-5为骨架的配体L~Ⅰ～L~Ⅴ，并合成了其稀土硝酸盐和苦味酸盐的10个系列共51个稀土配合物。以水杨酰苄胺和2-水杨酰胺甲基吡啶为功能末端基合成出两个以苯并-12-冠-4为骨架的配体L~Ⅵ和L~Ⅶ，并合成了其稀土硝酸盐和苦味酸盐的4个系列共18个稀土配合物。以水杨酰苄胺为功能末端基合成出一个以苯并-18-冠-6为骨架的配体L~Ⅷ，并合成了其4个稀土硝酸盐配合物。论文对配合物的超分子结构进行了深入研究，探讨了不同骨架和末端基对配合物结构的影响以及分子间氢键、π-π堆积在构筑新颖超分子结构中的作用。
第三章：对配体L~Ⅰ～L~Ⅷ的铕、铽配合物进行了荧光性质研究。结果表明，所有末端基对稀土离子均具有良好的敏化作用。配体的骨架结构、功能末端基以及抗衡阴离子对稀土配合物的荧光性能均产生一定影响。
第四章：以苯并-15-冠-5、二氮杂-18-冠-6、环状多胺cyclen和杯[4]芳烃为骨架设计合成出四个带臂大环类配体L~Ⅸ～L~Ⅻ，并合成出配体与稀土硝酸盐的4个系列共19个配合物，并对部分稀土发光配合物的荧光性质进行了考察。研究表明，所合成的稀土发光配合物发光性能良好，且配体L~Ⅺ和L~Ⅻ硝酸铕配合物可通过可见光激发发光，具有良好的生物体系应用前景。
第五章：对配体L~Ⅰ、L~Ⅱ和L~Ⅷ硝酸铽配合物的阳离子荧光传感识别进行了研究，研究结果表明，在所测试的十几种金属离子中，配合物对Hg~(2+)具有特别的荧光响应；对配体L~Ⅵ硝酸铽配合物的溶剂分子识别进行了研究，结果表明，配合物对乙腈分子具有特别的荧光响应。
本论文涉及到的配体：
L~Ⅰ：4，5-二{[2’-(N-苄基)甲酰基苯氧基]-甲基}-苯并-15-冠-5
L~Ⅱ：4，5-二{{2’-[N-(2”-胺甲基吡啶)]甲酰基苯氧基}-甲基}-苯并-15-冠-5
L~Ⅲ：4，5-二{{2’-[N-(3”-胺甲基吡啶)]甲酰基苯氧基}-甲基}-苯并-15-冠-5
L~Ⅳ：4，5-二{[2’-(N-苯基)甲酰基苯氧基]-甲基}-苯并-15-冠-5
L~Ⅴ：4，5-二{[2’-(N-呋喃甲基)甲酰基苯氧基]-甲基}-苯并-15-冠-5
L~Ⅵ：4，5-二{[2’-(N-苄基)甲酰基苯氧基]-甲基}-苯并-12-冠-4
L~Ⅶ：4，5-二{{2’-[N-(2”-胺甲基吡啶)]甲酰基苯氧基}-甲基}-苯并-12-冠-4
L~Ⅷ：4，5-二{[2’-(N-苄基)甲酰基苯氧基]-甲基}-苯并-18-冠-6
L~Ⅸ：4，5-二[(2’-甲酸苯氧基)]-甲基-苯并-15-冠-5
L~Ⅹ：1，10-二[N-苄基-4’(4”-三联吡啶)]-4，7，13，16-四氧杂环十八烷
L~Ⅺ：1，4，7，10-四(N，N-二异丙基甲酰基甲基)-1，4，7，10-四氮杂环十二烷
L~Ⅻ：5，11，17，23-四(1，1-二甲基乙基)-25，27-二[(N-苄基甲酰基)甲氧基]-26，28-二羟基杯[4]芳烃
Rare-earth ions have unique electronic structure and bonding characteristics, so rareearth complexes show distinct luminescent properties. Recently, the design and assemblyof functional luminescent rare-earth complexes have become a challenging issue.Amide-type ligands have the advantages in simple synthesis, adjustable structure andchangeable sensitive conjugate groups, which make their complexes indicating goodluminescent properties. In order to investigate the coordination properties of the pendantmacrocyclic ligands with rare earth ions, and the influence of different skeleton and thefunctional terminal groups of the ligands and different anions to luminescent properties ofthe rare earth complexes, eight kinds of pendant macrocyclic amide type ligands L~Ⅰ～L~Ⅷ,four kinds of other pendant macrocyclic ligands L~Ⅸ～L~Ⅻand their rare earth complexeshave been synthesized and characterized in this dissertation. Then the luminescentproperties of the complexes were systematically studied, and the ion-selective experimentsof the terbium nitrate complexes with ligands L~Ⅰ, L~Ⅱand L~Ⅲand the solvent molecularrecognition of the terbium nitrate complexes with ligand L~Ⅵwere accomplishedsubsequently.
The dissertation includes following five chapters:
Chapter 1: A brief review of investigation progress of rare earth luminescent complexesand luminescent chemosensor were summarized.
Chapter 2: Pendant macrocyclic ligands L~Ⅰ～L~Ⅴhave been designed and synthesizedusing five kind of amide-type terminal groups as arms and benzo-15-crown-5 as theskeleton, and 51 rare earth complexes include rare earth nitrate and picrate with L~Ⅰ～L~Ⅴhave been synthesized and characterized. Two ligands L~Ⅵand L~Ⅶhave been designedand synthesized containing different terminal groups and using benzo-12-crown-4 as theskeleton, and their 18 rare earth nitrate and picrate complexes also have been synthesizedand characterized. The ligands L~Ⅷhave been synthesized using N-benzylsalicylamide asterminal group and using benzo-18-crown-6 as the skeleton, and four rare earth nitratecomplexes also have been synthesized and characterized. Based on crystal diffractionanalysis, the influence of the counter anions to the complex structures, hydrogen bondsandπ-πstacking interactions in building novel supermolecule, and space topological structures in supermolecules have been studied.
Chapter 3: Photoluminescence studies of europium and terbium complexes show that allthe terminal groups have good sensitive function to europium and terbium ions. Theskeletons and terminal groups of the ligands, the counter anions have effects on theluminescent properties of the rare earth complexes.
Chapter 4: Four pendant macrocyclic ligands have been synthesized usingbenzo-15-crown-5, diaza-18-crown-6, cyclen and calix[4]arene as the skeleton, and 19rare earth nitrate complexes were synthesized. Then the luminescent properties of a part ofthe luminescent rare earth complexes were studied. The results indicated that the rare earthcomplexes had good luminescent properties. Because the luminescence of europiumnitrate complexes with the ligand of L~Ⅺand L~Ⅻcould stimulated by visible light, theyhad a good application potentiality in biosystem.
Chapter 5: The ion-selective experiments of the terbium nitrate complexes with ligandsL~Ⅰ, L~Ⅱand L~Ⅷhad been studied, the results indicated that the complexes had specialfluorescent response to Hg~(2+) in the test of a dozen of metal ions; then the study of solventmolecular recognition of the terbium nitrate complex with ligand L~Ⅵshown that thecomplex has distinct fluorescent response in acetonitrile.
The ligands involved in the dissertation are listed as follows:
L~Ⅰ: 4,5-bis {{[2'-(N-benzylaminoformyl)]-phenoxyl}methyl}-benzo-15-crown-5
L~Ⅱ: 4, 5-bi {{2'-[2"-(N-methylpyridineaminoformyl)]phenoxyl}methyl} benzo-15-crown-5
L~Ⅲ: 4,5-bi {{2'-[3"-(N-methylpyridineaminoformyl)]phenoxyl} methyl} benzo-15-crown-5
L~Ⅳ: 4,5-his {[(2'-phenylaminoformyl)-phenoxyl]methyl}-benzo- 15-crown-5
L~Ⅴ: 4,5-bi{ [2'-(N-(2"-methylfuranaminoformyl)phenoxyl]methyl}-benzo-15-crown-5
L~Ⅵ: 4,5-bis {[(2'-benzylaminoformyl)-phenoxyl]methyl}-benzo-12-crown-4
L~Ⅶ: 4, 5-bi {{2'-[2"-(N-methylpyridineaminoformyl)]phenoxyl} methyl} benzo-12-crown-4
L~Ⅷ: 4,5-bis {[(2'-benzylaminoformyl)-phenoxyl]methyl}-benzo-18-crown-6
L~Ⅸ: 4,5-bis {[(2'-carboxyphenoxy)-phenoxyl]methyl }-benzo-15-crown-5
L~Ⅹ: 1,10-bis [N-benzyl-4'(4"-terpyridine)]-4,7,13,16- tetraoxacyclooctadecane
L~Ⅺ: 1,4,7,10-Tetrakis[(N,N-bisisopropylmethylcarbamoyl)methyl]-1,4,7,10-tetra-azacyclododecane
L~Ⅻ: 5,11,17,23-Tetrakis(1,1-dimethylethyl)-25,27-bis(N-benzylaminoformyl)-26,28-dihydroxycalix[4]arene
本论文共分五章：
第一章：简要综述了近年来稀土发光配合物和荧光化学传感器的研究进展。
第二章：以五种不同种类水杨酰胺为功能末端基设计合成出以苯并-15-冠-5为骨架的配体L~Ⅰ～L~Ⅴ，并合成了其稀土硝酸盐和苦味酸盐的10个系列共51个稀土配合物。以水杨酰苄胺和2-水杨酰胺甲基吡啶为功能末端基合成出两个以苯并-12-冠-4为骨架的配体L~Ⅵ和L~Ⅶ，并合成了其稀土硝酸盐和苦味酸盐的4个系列共18个稀土配合物。以水杨酰苄胺为功能末端基合成出一个以苯并-18-冠-6为骨架的配体L~Ⅷ，并合成了其4个稀土硝酸盐配合物。论文对配合物的超分子结构进行了深入研究，探讨了不同骨架和末端基对配合物结构的影响以及分子间氢键、π-π堆积在构筑新颖超分子结构中的作用。
第三章：对配体L~Ⅰ～L~Ⅷ的铕、铽配合物进行了荧光性质研究。结果表明，所有末端基对稀土离子均具有良好的敏化作用。配体的骨架结构、功能末端基以及抗衡阴离子对稀土配合物的荧光性能均产生一定影响。
第四章：以苯并-15-冠-5、二氮杂-18-冠-6、环状多胺cyclen和杯[4]芳烃为骨架设计合成出四个带臂大环类配体L~Ⅸ～L~Ⅻ，并合成出配体与稀土硝酸盐的4个系列共19个配合物，并对部分稀土发光配合物的荧光性质进行了考察。研究表明，所合成的稀土发光配合物发光性能良好，且配体L~Ⅺ和L~Ⅻ硝酸铕配合物可通过可见光激发发光，具有良好的生物体系应用前景。
第五章：对配体L~Ⅰ、L~Ⅱ和L~Ⅷ硝酸铽配合物的阳离子荧光传感识别进行了研究，研究结果表明，在所测试的十几种金属离子中，配合物对Hg~(2+)具有特别的荧光响应；对配体L~Ⅵ硝酸铽配合物的溶剂分子识别进行了研究，结果表明，配合物对乙腈分子具有特别的荧光响应。
本论文涉及到的配体：
L~Ⅰ：4，5-二{[2’-(N-苄基)甲酰基苯氧基]-甲基}-苯并-15-冠-5
L~Ⅱ：4，5-二{{2’-[N-(2”-胺甲基吡啶)]甲酰基苯氧基}-甲基}-苯并-15-冠-5
L~Ⅲ：4，5-二{{2’-[N-(3”-胺甲基吡啶)]甲酰基苯氧基}-甲基}-苯并-15-冠-5
L~Ⅳ：4，5-二{[2’-(N-苯基)甲酰基苯氧基]-甲基}-苯并-15-冠-5
L~Ⅴ：4，5-二{[2’-(N-呋喃甲基)甲酰基苯氧基]-甲基}-苯并-15-冠-5
L~Ⅵ：4，5-二{[2’-(N-苄基)甲酰基苯氧基]-甲基}-苯并-12-冠-4
L~Ⅶ：4，5-二{{2’-[N-(2”-胺甲基吡啶)]甲酰基苯氧基}-甲基}-苯并-12-冠-4
L~Ⅷ：4，5-二{[2’-(N-苄基)甲酰基苯氧基]-甲基}-苯并-18-冠-6
L~Ⅸ：4，5-二[(2’-甲酸苯氧基)]-甲基-苯并-15-冠-5
L~Ⅹ：1，10-二[N-苄基-4’(4”-三联吡啶)]-4，7，13，16-四氧杂环十八烷
L~Ⅺ：1，4，7，10-四(N，N-二异丙基甲酰基甲基)-1，4，7，10-四氮杂环十二烷
L~Ⅻ：5，11，17，23-四(1，1-二甲基乙基)-25，27-二[(N-苄基甲酰基)甲氧基]-26，28-二羟基杯[4]芳烃
Rare-earth ions have unique electronic structure and bonding characteristics, so rareearth complexes show distinct luminescent properties. Recently, the design and assemblyof functional luminescent rare-earth complexes have become a challenging issue.Amide-type ligands have the advantages in simple synthesis, adjustable structure andchangeable sensitive conjugate groups, which make their complexes indicating goodluminescent properties. In order to investigate the coordination properties of the pendantmacrocyclic ligands with rare earth ions, and the influence of different skeleton and thefunctional terminal groups of the ligands and different anions to luminescent properties ofthe rare earth complexes, eight kinds of pendant macrocyclic amide type ligands L~Ⅰ～L~Ⅷ,four kinds of other pendant macrocyclic ligands L~Ⅸ～L~Ⅻand their rare earth complexeshave been synthesized and characterized in this dissertation. Then the luminescentproperties of the complexes were systematically studied, and the ion-selective experimentsof the terbium nitrate complexes with ligands L~Ⅰ, L~Ⅱand L~Ⅲand the solvent molecularrecognition of the terbium nitrate complexes with ligand L~Ⅵwere accomplishedsubsequently.
The dissertation includes following five chapters:
Chapter 1: A brief review of investigation progress of rare earth luminescent complexesand luminescent chemosensor were summarized.
Chapter 2: Pendant macrocyclic ligands L~Ⅰ～L~Ⅴhave been designed and synthesizedusing five kind of amide-type terminal groups as arms and benzo-15-crown-5 as theskeleton, and 51 rare earth complexes include rare earth nitrate and picrate with L~Ⅰ～L~Ⅴhave been synthesized and characterized. Two ligands L~Ⅵand L~Ⅶhave been designedand synthesized containing different terminal groups and using benzo-12-crown-4 as theskeleton, and their 18 rare earth nitrate and picrate complexes also have been synthesizedand characterized. The ligands L~Ⅷhave been synthesized using N-benzylsalicylamide asterminal group and using benzo-18-crown-6 as the skeleton, and four rare earth nitratecomplexes also have been synthesized and characterized. Based on crystal diffractionanalysis, the influence of the counter anions to the complex structures, hydrogen bondsandπ-πstacking interactions in building novel supermolecule, and space topological structures in supermolecules have been studied.
Chapter 3: Photoluminescence studies of europium and terbium complexes show that allthe terminal groups have good sensitive function to europium and terbium ions. Theskeletons and terminal groups of the ligands, the counter anions have effects on theluminescent properties of the rare earth complexes.
Chapter 4: Four pendant macrocyclic ligands have been synthesized usingbenzo-15-crown-5, diaza-18-crown-6, cyclen and calix[4]arene as the skeleton, and 19rare earth nitrate complexes were synthesized. Then the luminescent properties of a part ofthe luminescent rare earth complexes were studied. The results indicated that the rare earthcomplexes had good luminescent properties. Because the luminescence of europiumnitrate complexes with the ligand of L~Ⅺand L~Ⅻcould stimulated by visible light, theyhad a good application potentiality in biosystem.
Chapter 5: The ion-selective experiments of the terbium nitrate complexes with ligandsL~Ⅰ, L~Ⅱand L~Ⅷhad been studied, the results indicated that the complexes had specialfluorescent response to Hg~(2+) in the test of a dozen of metal ions; then the study of solventmolecular recognition of the terbium nitrate complex with ligand L~Ⅵshown that thecomplex has distinct fluorescent response in acetonitrile.
The ligands involved in the dissertation are listed as follows:
L~Ⅰ: 4,5-bis {{[2'-(N-benzylaminoformyl)]-phenoxyl}methyl}-benzo-15-crown-5
L~Ⅱ: 4, 5-bi {{2'-[2"-(N-methylpyridineaminoformyl)]phenoxyl}methyl} benzo-15-crown-5
L~Ⅲ: 4,5-bi {{2'-[3"-(N-methylpyridineaminoformyl)]phenoxyl} methyl} benzo-15-crown-5
L~Ⅳ: 4,5-his {[(2'-phenylaminoformyl)-phenoxyl]methyl}-benzo- 15-crown-5
L~Ⅴ: 4,5-bi{ [2'-(N-(2"-methylfuranaminoformyl)phenoxyl]methyl}-benzo-15-crown-5
L~Ⅵ: 4,5-bis {[(2'-benzylaminoformyl)-phenoxyl]methyl}-benzo-12-crown-4
L~Ⅶ: 4, 5-bi {{2'-[2"-(N-methylpyridineaminoformyl)]phenoxyl} methyl} benzo-12-crown-4
L~Ⅷ: 4,5-bis {[(2'-benzylaminoformyl)-phenoxyl]methyl}-benzo-18-crown-6
L~Ⅸ: 4,5-bis {[(2'-carboxyphenoxy)-phenoxyl]methyl }-benzo-15-crown-5
L~Ⅹ: 1,10-bis [N-benzyl-4'(4"-terpyridine)]-4,7,13,16- tetraoxacyclooctadecane
L~Ⅺ: 1,4,7,10-Tetrakis[(N,N-bisisopropylmethylcarbamoyl)methyl]-1,4,7,10-tetra-azacyclododecane
L~Ⅻ: 5,11,17,23-Tetrakis(1,1-dimethylethyl)-25,27-bis(N-benzylaminoformyl)-26,28-dihydroxycalix[4]arene
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