苯甲酰胺衍生物及其铕配合物的合成与荧光性能
|
摘要
酰胺类化合物具有合成简单、结构多变及配位末端基可调等特性,对稀土离子有较好的识别配位能力,本文通过改变配体末端基官能团设计合成出了13种新的苯甲酰胺衍生物以及10种结构新颖并具有良好荧光性能的稀土有机配合物。其研究工作分为以下四个部分：
(1)以苯甲酰胺为基本骨架,合成了6种新的含有酯基的苯甲酰胺衍生物[N-苄基-2-(取代酰氧基)苯甲酰胺],通过核磁氢谱、质谱、元素分析及红外光谱等分析手段对目标化合物及其中间体进行了结构表征。
(2)以所合成的N-苄基-2-(取代酰氧基)苯甲酰胺为配体,Eu(Ⅲ)为中心离子,合成了6种新的铕-N-苄基-2-(取代酰氧基)苯甲酰胺荧光配合物。通过EDTA配位滴定分析、摩尔电导、元素分析、红外光谱、紫外光谱及热分析等手段确定了目标配合物的结构和组成；采用荧光光谱仪研究了目标配合物的荧光性能。实验结果表明：6种含酯基的化合物N-苄基-2-(取代酰氧基)苯甲酰胺能够与铕离子形成稳定的配合物,铕-N-苄基-2-(苯甲酰氧基)苯甲酰胺、铕-N-苄基-2-(对甲基苯甲酰氧基)苯甲酰胺、铕-N-苄基-2-(对氯苯甲酰氧基)苯甲酰胺、铕-N-苄基-2-(对甲氧基苯甲酰氧基)苯甲酰胺及铕-N-苄基-2-(间氯苯甲酰氧基)苯甲酰胺等5种配合物发出了铕离子的红色特征荧光,单色性好,荧光强度大；铕-N-苄基-2-(苯乙酰氧基)苯甲酰胺配合物发出了配体N-苄基-2-(苯乙酰氧基)苯甲酰胺的绿色荧光,研究表明配合物的结构差别导致了配合物荧光颜色的不同。
(3)以苯甲酰胺为基本骨架,合成了7种新的含有亚氨基的苯甲酰胺衍生物[N-苄基-2-(芳基亚氨基氨甲酰基甲氧基)苯甲酰胺],通过核磁氢谱、质谱、元素分析及红外光谱等分析手段对目标化合物及其中间体进行了结构表征。
(4)以所合成的N-苄基-2-(芳基亚氨基氨甲酰基甲氧基)苯甲酰胺为配体,Eu(Ⅲ)为中心离子,合成了4种新的铕-N-苄基-2-(芳基亚氨基氨甲酰基甲氧基)苯甲酰胺荧光配合物。7种含亚氨基的化合物中只有N-苄基-2-(间硝基苯亚氨基氨甲酰基甲氧基)苯甲酰胺、N-苄基-2-(对甲氧基苯亚氨基氨甲酰基甲氧基)苯甲酰胺、N-苄基-2-(对羟基苯亚氨基氨甲酰基甲氧基)苯甲酰胺、N-苄基-2-(苯亚氨基氨甲酰基甲氧基)苯甲酰胺等4种能够与中心铕离子形成稳定的配合物,荧光光谱分析结果表明4种配合物所发出的荧光为配体荧光,铕离子的微扰使得配体的发光强度增加。
With unusual characteristics of simple synthesitic methods, changeable structures and adjustable terminal groups, amide ligands have high selectivety and good regulatory to lanthanide ions. Thirteen new benzamide derivatives and ten complexes with novel structure and excellent luminescent properties have been synthesized in this paper. This work contains four parts as follows:
(1) Six new compounds N-benzyl-2-(substituted acyloxy)benzamide with esters have been synthesized with benzamide as the basic framework. All benzamide derivatives and their intermediates have been characterized by 1H NMR, MS, elemental analysis and FT-IR spectrum.
(2) Six new fluorescence complexes of Europium with the ligands of N-benzyl-2-(substituted acyloxy)benzamides have been synthesized. Molecular compositions and strctures were characterized with EDTA titrimetric methods, molar conductance analysis, elemental analysis, FT-IR and UV spectrum analysis, thermal analysis and so on. The luminescence properties of the complexes have also been investigated. Results showed that the ligands with ester group have high selectivety and coordinations to europium ions. The complexes Eu-N-benzyl-2-(benzoyloxy)benzamide, Eu-N-benzyl-2-(p-methyl-benzoyloxy)benzamide, Eu-N-benzyl-2-(p-chloro-benzoyloxy) benzamide, Eu-N-benzyl-2-(p-methoxyl-benzoyloxy)benzamide, Eu-N-benzyl-2-(3-chloro-benzoyloxy)benzamide showed red fluorescence with good single properties and high luminescence intensities. And another complex Eu-N-benzyl-2-(phenyl-acetoxy)benzamide showed green fluorescence which was emittde by N-benzyl-2-(phenyl-acetoxy)benzamide. This study showed that the difference among the complexes leads to the different color of the luminescence properties.
(3) Seven new compounds with imino groups have been synthesized with benzamide as the basic framework. All benzamide derivatives and their intermediates have been characterized by 1H NMR, MS, elemental analysis and FT-IR spectrum.
(4) Four new fluorescence complexes of Europium with the ligands N-benzyl-2-(aryliminocarbamoylmethoxy)benzamide have been synthesized. Their molecular compositions and strctures were characterized by EDTA titrimetric methods, molar conductance analysis, elemental analysis, FT-IR and UV spectrum analysis, thermal studies and so on. The luminescence properties of the comlexes have also been investigated. Results showed that four complexes with ligands N-benzyl- 2-(3-nitro-benzyliminocarbamoylmethoxy)benzamide, N-benzyl-2-(4-methoxyl-ben zyliminocarbamoylmethoxy)benzamide,N-benzyl-2-(4-hydrox-yl-benzyliminocarb-amoylmethoxy)benzamide, N-benzyl-2-(benzyliminoarbamoylmethoxy)benzamide possess excellent stabilities. And the flourescence spectucm results showed that they all admitted the flourescence of the ligands. It is Europium who enhanced the luminescence intensity of ligands.
(1)以苯甲酰胺为基本骨架,合成了6种新的含有酯基的苯甲酰胺衍生物[N-苄基-2-(取代酰氧基)苯甲酰胺],通过核磁氢谱、质谱、元素分析及红外光谱等分析手段对目标化合物及其中间体进行了结构表征。
(2)以所合成的N-苄基-2-(取代酰氧基)苯甲酰胺为配体,Eu(Ⅲ)为中心离子,合成了6种新的铕-N-苄基-2-(取代酰氧基)苯甲酰胺荧光配合物。通过EDTA配位滴定分析、摩尔电导、元素分析、红外光谱、紫外光谱及热分析等手段确定了目标配合物的结构和组成；采用荧光光谱仪研究了目标配合物的荧光性能。实验结果表明：6种含酯基的化合物N-苄基-2-(取代酰氧基)苯甲酰胺能够与铕离子形成稳定的配合物,铕-N-苄基-2-(苯甲酰氧基)苯甲酰胺、铕-N-苄基-2-(对甲基苯甲酰氧基)苯甲酰胺、铕-N-苄基-2-(对氯苯甲酰氧基)苯甲酰胺、铕-N-苄基-2-(对甲氧基苯甲酰氧基)苯甲酰胺及铕-N-苄基-2-(间氯苯甲酰氧基)苯甲酰胺等5种配合物发出了铕离子的红色特征荧光,单色性好,荧光强度大；铕-N-苄基-2-(苯乙酰氧基)苯甲酰胺配合物发出了配体N-苄基-2-(苯乙酰氧基)苯甲酰胺的绿色荧光,研究表明配合物的结构差别导致了配合物荧光颜色的不同。
(3)以苯甲酰胺为基本骨架,合成了7种新的含有亚氨基的苯甲酰胺衍生物[N-苄基-2-(芳基亚氨基氨甲酰基甲氧基)苯甲酰胺],通过核磁氢谱、质谱、元素分析及红外光谱等分析手段对目标化合物及其中间体进行了结构表征。
(4)以所合成的N-苄基-2-(芳基亚氨基氨甲酰基甲氧基)苯甲酰胺为配体,Eu(Ⅲ)为中心离子,合成了4种新的铕-N-苄基-2-(芳基亚氨基氨甲酰基甲氧基)苯甲酰胺荧光配合物。7种含亚氨基的化合物中只有N-苄基-2-(间硝基苯亚氨基氨甲酰基甲氧基)苯甲酰胺、N-苄基-2-(对甲氧基苯亚氨基氨甲酰基甲氧基)苯甲酰胺、N-苄基-2-(对羟基苯亚氨基氨甲酰基甲氧基)苯甲酰胺、N-苄基-2-(苯亚氨基氨甲酰基甲氧基)苯甲酰胺等4种能够与中心铕离子形成稳定的配合物,荧光光谱分析结果表明4种配合物所发出的荧光为配体荧光,铕离子的微扰使得配体的发光强度增加。
With unusual characteristics of simple synthesitic methods, changeable structures and adjustable terminal groups, amide ligands have high selectivety and good regulatory to lanthanide ions. Thirteen new benzamide derivatives and ten complexes with novel structure and excellent luminescent properties have been synthesized in this paper. This work contains four parts as follows:
(1) Six new compounds N-benzyl-2-(substituted acyloxy)benzamide with esters have been synthesized with benzamide as the basic framework. All benzamide derivatives and their intermediates have been characterized by 1H NMR, MS, elemental analysis and FT-IR spectrum.
(2) Six new fluorescence complexes of Europium with the ligands of N-benzyl-2-(substituted acyloxy)benzamides have been synthesized. Molecular compositions and strctures were characterized with EDTA titrimetric methods, molar conductance analysis, elemental analysis, FT-IR and UV spectrum analysis, thermal analysis and so on. The luminescence properties of the complexes have also been investigated. Results showed that the ligands with ester group have high selectivety and coordinations to europium ions. The complexes Eu-N-benzyl-2-(benzoyloxy)benzamide, Eu-N-benzyl-2-(p-methyl-benzoyloxy)benzamide, Eu-N-benzyl-2-(p-chloro-benzoyloxy) benzamide, Eu-N-benzyl-2-(p-methoxyl-benzoyloxy)benzamide, Eu-N-benzyl-2-(3-chloro-benzoyloxy)benzamide showed red fluorescence with good single properties and high luminescence intensities. And another complex Eu-N-benzyl-2-(phenyl-acetoxy)benzamide showed green fluorescence which was emittde by N-benzyl-2-(phenyl-acetoxy)benzamide. This study showed that the difference among the complexes leads to the different color of the luminescence properties.
(3) Seven new compounds with imino groups have been synthesized with benzamide as the basic framework. All benzamide derivatives and their intermediates have been characterized by 1H NMR, MS, elemental analysis and FT-IR spectrum.
(4) Four new fluorescence complexes of Europium with the ligands N-benzyl-2-(aryliminocarbamoylmethoxy)benzamide have been synthesized. Their molecular compositions and strctures were characterized by EDTA titrimetric methods, molar conductance analysis, elemental analysis, FT-IR and UV spectrum analysis, thermal studies and so on. The luminescence properties of the comlexes have also been investigated. Results showed that four complexes with ligands N-benzyl- 2-(3-nitro-benzyliminocarbamoylmethoxy)benzamide, N-benzyl-2-(4-methoxyl-ben zyliminocarbamoylmethoxy)benzamide,N-benzyl-2-(4-hydrox-yl-benzyliminocarb-amoylmethoxy)benzamide, N-benzyl-2-(benzyliminoarbamoylmethoxy)benzamide possess excellent stabilities. And the flourescence spectucm results showed that they all admitted the flourescence of the ligands. It is Europium who enhanced the luminescence intensity of ligands.
引文
[1]Takahiro T, Yukihiro Y, Yohei Ikeji. Raman Spectroscopic Study on the Coordinati-on Behavior of Rare Earth Ions in N-Methylacetamide. J. Phys. Chem. B,2008, 112(42):13355-13358
[2]Felipe G, Enrique G P, Marta I, et al.. Isolated Hexanuclear Hydroxo Lanthanide Seary Building Units in a Rare-Earth Polymeric Framework Based on p-Sulfona-tocalix[4] arene. Crystal Growth and Design,2010,10(1):128-134
[3]苏锵.稀土化学.郑州：河南科学技术出版社,1993,8-10
[4]Masato O, Marcin K, Iker D R, et al.. Rare-Earth Metal Alkyl and Hydride Comple-xes Stabilized by a Cyclen-Derived [NNNN] Macrocyclic Ancillary Ligand. J. Am. Chem. Soc.,2008,130(22):6920-6921
[5]Roof I P, Mark D S, Park S, et al.. EuKNaTaO5:Crystal Growth, Structure and Photolumi-nescence Property. J. Am. Chem. Soc.,2009,131(12):4202-4203
[6]Ohashi M, Konkol M, Rosal I D. Rare-Earth Metal Alkyl and Hydride Complexes Stabilized by a Cyclen-Derived [NNN'N'] Macrocyclic Ancillary Ligand Romuald Poteau, Laurent Maron and Jun Okuda. J. Am. Chem. Soc.,2008, 130(22):6920-6921
[7]Felipe G, Enrique G P, Marta I, et al.. Isolated Hexanuclear Hydroxo Lanthanide Secondary Building Units in a Rare-Earth Polymeric Framework Based on p-Sulfonatocalix[4] arene. Crystal Growth and Design,2010,10(1):128-134
[8]Wang J W, Tanner P A. Upconversion for White Light Generation by a Single Compound. J. A. C. S.,2010,132:947-949
[9]Weidenthaler C, Pommerin A, Felderhoff M, et al.. Complex Rare-Earth Aluminum Hydrides:Mechanochemical Preparation, Crystal Structure and Potential for Hydrogen Sto- rage. J. A. C. S.,2009,131:16735-16743
[10]Zhang Z J, Xu X P, Li W Y, et al.. Synthesis of Rare-Earth Metal Amides Bearing an Imidazolidine-Bridged Bis (phenolato) Ligand and Their Application in the Polymerization of L-Lactide. Inorg. Chem.,2009,48:5715-5724
[11]Gerd W R, Florian A R, Mei Z P, et al.. Flexible Coordination Mode of a Donor Functionalized Terphenyl Ligand in Monomeric Cp-Based Lanthanocenes. Organometallics,2009,28:5277-5280
[12]郭栋才,张为,舒万艮,等.铽芳香羧酸丙烯酰胺三元配合物的合成及发光性能研究.稀土,2006,27(2)：22-29
[13]刘胜利,黄莉,禹良才,等.对三氟甲基苯甲酸和2,2-联吡啶双核铽配合物的合成、晶体结构及发光性质.无机化学学报,2009,25(6)：1102-1105
[14]江艳华,秦玉升,乔立军,等.稀土三元催化剂下正辛酸缩水甘油酯-二氧化碳-环氧丙烷的三元共聚合.应用化学,2009,26(7)：770-774
[15]Wessman S I. Intramolecular energy transfer the fluorescence of complexes of europium. Chem. Phys.,1942,10(4):214-217
[16]Crosby G A, Whan R E, Alire R M. Intramolecular energy transfer in rare earth chelates. Chem. Phys.,1961,34(3):734-738
[17]Susumu S, Masanobu W. Relations between intramolecular energy transfer effici-encies and triplet state energies in rare earth β-diketone chelates. Bull. Chem. Soc. Jpn.,1970,43(7):1955
[18]李建宇.稀土发光材料及其应用.北京：化学工业出版社,2004,2
[19]Liu D, Wang Z G, Yu H, et al.. Fluorescence properties of novel rare earth com-plexes using carboxyl-containing polyaryletherketones as macromolecular ligands. European Polymer Journal,2009,45:2260-2268
[20]Silversmith A J, Nguyen T T, Campbell D L, et al.. Fluorescence yield in rare ear-th doped sol-gel silicate glasses. Journal of Luminescence,2009,129:1501-1504
[21]Bernard M, Lena B, Patrick G, et al.. Research of green emitting rare-earth doped materials as potential quantum-cutter. Optical Materials,2008,30:1083-1087
[22]Klauth P, Joschko A, Ustohal P, et al.. Light fiber optic probe for measuring internal breakthrough of rare earth ionlabelled microspheres in porous media under unsaturated conditions. Colloids and Surfaces A:Physicochem. and Eng. Asp-ects,2008,325:173-179
[23]Ashokan A, Menon D, Nair S, et al.. A molecular receptor targeted, hydroxyapa-tite nanocrystal based multi-modal contrast agent. Biomaterials,2010,31: 2606-2616
[24]李昶红,郭栋才,杨颖群,等.一维链状铽配位聚合物{[Tb(p-MBA)2 (H2O)2]2·(4,4'-bidy)2}n的合成、晶体结构及荧光分析.无机化学学报,2006,22(11)：2085-2089
[25]郭栋才,苟丽宁,周悦,等.铕-芳香羧酸-丁二酸三元配合物的合成及荧光性能研究.材料研究学报,2009,23(3)：257-263
[26]Kido J, Nagai K, Ychashi. Electroluminescence in terbium complex. Chem. Lett, 1990,22(7):657-660
[27]Kwon Y S, Jung M H, Lee K R, et al.. Correlation of an infrared absorption with carriers in rare-earth monoantimonides. Physica B:Condensed Matter,1997, 240(1-2):88-91
[28]Kido J, Hayase H. Bright and light-emitting organic electroluminescent devices having an europium complex as an emitter. Appl. Phys. Lett,1994,65(17): 2124-2126
[29]Martinez A, Zenteno L A, Kuo J C K. Analysis of the fluorescence decay of MCVD Nd Al-codoped SiO2 fiber-preforms prepared by rare-earth chelate delivery. Optics Communications,1999,160(4-6):235-239
[30]Collins J M, Bartolo B D. Temperature and energy gap dependence of energy transfer between rare-earth ions in solids. Journal of Luminescence,1996, 69(5-6):335-341
[31]Balzali J C G., Murner H R, Chassat E, et al.. Strong enhancement of the lanthani-de-centred luminescence in complexes with 4-alkylated 2,2';6',2"-terpyridines. Dalton Trans.,2000,2809-2816
[32]Siddall T H. Effects of Structure of N,N-Disubstituted Amides on their Extraction of Actinide and Zirconium Nitrates and of Nitric Acid. J. Phys. Chem.,1960,64: 1863
[33]Norbert N L, Robert K, Funck J J, et al.. Extraction von Alkali-und Erdalkalimetall pikraten auswasscrigen Losungen in Methylenchlorid durch ungeladene zayklische Ionophoren Quantitat Interpretation. Helvetica Chimica, Acta,1978,61(190):2019-2039
[34]Schefer U, Ammann D, Pretsch E, et al.. Neutral Carrier Bassed Ca2+-Slectrode Electrode with Detection Limit in the Sub-Nanomolar Range. Anal. Chem.,1986, 58:2282-2285
[35]Narita H, Yaita T, Tamura K, et al.. Solvent Extraction of Trivant Lathanoid Ions With N,N-Dimethyl-N,N'-Diphenl-3-Oxapenatanediamide. Radiochim. Acta.,1998,81:223-226
[36]孙国新,韩景田,李玉兰,等.N,N,N’,N’-四已基丙二酰胺从硝酸介质中萃取铀(Ⅵ).应用化学,1998,15(4)：29-32
[37]康文,刘峙嵘,李传茂,等.萃取剂N-正丁基二乙酰亚胺的合成及其对铈(Ⅳ)的萃取行为.稀土,2006,27(3)：57-60
[38]Piguet C, Bulnzli J C G, Bernardinelli G, et al.. Lanthanide Podates with Prede-termined Structural and Photophysical Properties:Strongly Luminescent Self-As-sembled Heterodinuclear d-f Complexes with a Segmental Ligand Containing Heterocyclic Imines and Carboxamide Binding Units. J. A. C. S,1996,118: 6681-6697
[39]Gunnlaugsson T, Parker D. Luminescent europium tetraazamacrocyclic complexes with wide range pH sensitivity. Chem. Commun,1998,511-512
[40]陆晓红,林秋月,孔黎春,等.N,N-双(2-吡啶甲酰胺)-1,2-乙烷双核稀土配合物的合成及与DNA的相互作用.化学研究与应用,2006,12(2)：1652-1656
[41]陆晓红,林秋月,胡瑞定,等.稀土N,N’-双(2-吡啶甲酰胺)-1,2-乙烷配合物合成及与DNA的作用.光谱学与光谱分析,2007,27(6)：1176-1180
[42]辛红,王晓菊.聚(苯乙烯-丙烯酰胺)负载氯化钕配合物在4-乙烯吡啶聚合反应中的催化性能.稀土,2002,23(1)：35-37
[43]张雪黎,罗来涛.A位掺杂LaSrCoO4对CO和C3H8氧化性能研究.环境科学与技术,2007,30(5)：70-72
[44]Thomas B, Sugunan S. Rare catalysts-earth (Ce3+, La3+, Sm3+, and RE3+) exch-anged Na-Y zeolites and K-10 clay as solid acid for the synthesis of benzoxazole via Beckmann rearrangement of salicylaldoxime. Microporous and Mesoporous Materials,2006,96(1-3):55-64
[45]钱德胜,程广斌,吕春绪.稀土金属在离子液体中催化甲苯的硝化反应.应用化学,2009,26(7)：757-761
[46]Grigoryan H A, Hambardzumyan A A, Mkrtchyan M V, et al.. a,P-Dehydropheny-lalanine choline esters, a new class of reversible inhibitors of human acetylcholin-esteras and butyrylcholinesterase. Chemico Biological Interactions,2008: 108-116
[47]Chai J F, Liu G S, Chaicharoen K, et al.. Cobalt-Catalyzed Carbonylative Polymerization of Azetidines. Macromolecules 2008,41:8980-8985
[48]Pang X, Chu C C. Synthesis, characterization and biodegradation of functiona-lized amino acid-based poly(ester amide)s. Biomaterials.2010,31:3745-3754
[49]徐旭,伍国琳,张琳.具有乙二醇侧链的聚谷氨酸酯的合成、表征及其两亲性.化学学报,2008,66(9)：1102-1106
[50]Mansour I B, Alouani K, Chauveau E. Synthesis and characterisation of poly-(ester-amide)s from aromatic bisoxazoline precursors. European Polymer Journal, 2010,46:814-820
[51]Bruno O, Brullo C, Bondavalli F.1-Methyl and 1-(2-hydroxyalkyl)-5-(3-alkyl/cy-clo-alkyl/phenyl/naphthylureido)-1H-pyrazole-4-carboxylic acid ethyl esters as potent human neutrophil chemotaxis inhibitors. Bioorganic and Medicinal Chemi-stry,2009,17:3379-3387
[52]Sondhi S M., Singh J, Kumar A. Synthesis of amidine and amide derivatives and their evaluation for anti-inflammatory and analgesic activities. European Journal of Medicinal Chemistry,2009,44:1010-1015
[53]Huszar J, Timar Z, Szalai K K. Novel bradykinin-1 antagonists containing a (l,2,3,4-tetrahydro-isoquinolin-1-yl)acetic acid scaffold. European Journal of Medicinal Chemistry,2008,43:1552-1558
[54]Zou Y, Liu W L, Gao S. Synthesis, structure and magnetic properties of carboxy-late-bridged polynuclear copper(II)-lanthanide(III) rings:[Ln(H2O)5(CuL)2] [Cu-L]·8H2O (Ln= La, Ce). Polyhedron.2004,23:2253-2258
[55]Cerchiaro G, Aquilano K, Filomeni G, et al.. Isatin-Schiff base copper(II) comple-xes and their influence on cellular viability. Journal of Inorganic Biochemistry. 2005,99:1433-1440
[56]何水样,陈军利,杨锐,等.水杨醛水杨酰腙及其稀土配合物的合成、波谱研究及生物活性.有机化学,2003,23(12)：1387-1392
[57]Harvey R G., Dai Q, Ran C Z. Regioselective arylation of 2'-deoxyribonucleo-sides on amido or imino sites by copper(II)-mediated direct coupling with aryl-boronic acids. Tetrahedron 2006,62:1764-1771
[58]Wang Q M, Yan B. Molecular assembly and photophysical properties of a novel luminescent terbium hybrid material with modified carboxyl group of P-amino-benzoic acid as a functional bridge. Materials Letters,2006,60:3420-3425
[59]Duan G J, Yang Y, Liu T H, et al.. Synthesis, characterization of the luminescent lanthanide complexes with (Z)-4-(4-methoxyphenoxy)-4-oxobut-2-enoic acid. Spectrochimica Acta Part A,2008,69:427-431
[60]Liu T, Duan G J, Zhang Y P, et al.. Synthesis and characterization of the luminescent lanthanide complexes with two similar benzoic acids [J]. Spectroch-imica Acta Part A,2009,74:843-848
[61]Shoko S, Hiroshi F, Yasuo Y, et al.. Asymmetric fluorination of b-keto esters catalyzed by chiral rare earth perfluorinated organophosphates Tetrahedron: Asymmetry,2006,175:504-507
[62]Nakayama Y, Sasaki K, Watanabe N, et al.. Ring-opening polymerization of six-membered cyclic esters catalyzed by tetrahydroborate complexes of rare earth metals. Polymer,2009,50 (20):4788-4793
[63]Merce A, Xavier R, Josep M S, et al.. A study of the degradation of ester-modified epoxy resins obtained by cationic copolymerization of DGEBA with y-lactones initiated by rare earth triflates. Polymer Degradation and Stability,2007,92(12): 2214-2222
[64]Geary W J. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coordination Chemistry Reviews, 1971,7(1):81-122
[65]黄量,于德全.紫外光谱在有机化学中的应用.北京：科学出版社,2000,12-16.
[66]郭栋才,王鑫,谭慧,等.铕-邻菲咯啉衍生物-脂肪酸配合物的合成及性能.中国有色金属学报,2008,18(11)：2111-2117
[67]Nakamato K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. New York:Hohn Wilry,1978,227-248
[68]Barbara P F, Rentzepis P M, Brus L E. Photochemical Kinetics of Salicylidenaniline. J. A. C. S.,1980,102(8):2786-2791
[69]Wu S L, Wu Y L, Yang Y S. Rare earth (Ⅲ) complexes with indole-derived acetylacetones II. luminescent intensity for europium (Ⅲ) and terbium (Ⅲ) complexes. Journal of Alloys and Compounds,1992,180(1-2):399-402
[70]Liu G F, Shi T S, Zhao Y N. Infrared and Raman spectra of complexes about rare earth nitrate with Schiff base from o-vanillin and 1-naphthylamine. Journal of Molecular Structure,1997,412(1-2):75-81
[71]Wang B D, Yang Z Y, Qin D D, et al.. Synthesis, characterization, cytotoxic activity and DNA-binding properties of the Ln (III) complexes with ethylenediiminobi (6-hydroxychromone-3-carbal dehyde) Schiff-base. Journal of Photochemistry and Photobiology A:Chemistry,2008,194(1,5):49-58
[72]Binnemans K, Deun R Van, Bruce D W, et al.. Influence of the lanthanide contraction on the transition temperatures of rare-earth containing metallom-esogens with Schiff base ligands. Chemical Physics Letters,1999,300(3-4,5): 509-514
[73]Liu Y C, Yang Z Y. Synthesis, crystal structure, antioxidation and DNA binding properties of binuclear Ho (III) complexes of Schiff-base ligands derived from 8-hydroxyquinoline-2-carboxyaldehyde and four aroylhydrazines. Journal of Organometallic Chemistry,2009,694(19):3091-3101
[74]Liu Y C, Yang Z Y. Crystal structures, antioxidation and DNA binding properties of Eu (III) complexes with Schiff-base ligands derived from 8-hydroxyquino-line-2-carboxy-aldehyde and three aroylhydrazines. Journal of Inorganic Biochemistry,2009,103(7):1014-1022
[75]Kaczmarek S M, Leniec G. Spectral and magnetic properties of macroacyclic and macrobicyclic Schiff base RE complexes. Journal of Non-Crystalline Solids,2009, 355(24-27):1325-1332
[76]Leniec G, Kaczmarek S M, Typek J, et al.. FT-IR, ESI and EPR studies of a Dy(Ⅲ) Schiff base podand complex. Journal of Non-Crystalline Solids,2009, 35(24-27):1355-1359
[77]Solomon V R, Hu C K, Lee H, et al.. Hybrid pharmacophore design and synthesis of isatin-benzothiazole analogs for their anti-breast cancer activity. Bioorganic & Medicinal Chemistry,2009,17:7585-7592
[2]Felipe G, Enrique G P, Marta I, et al.. Isolated Hexanuclear Hydroxo Lanthanide Seary Building Units in a Rare-Earth Polymeric Framework Based on p-Sulfona-tocalix[4] arene. Crystal Growth and Design,2010,10(1):128-134
[3]苏锵.稀土化学.郑州：河南科学技术出版社,1993,8-10
[4]Masato O, Marcin K, Iker D R, et al.. Rare-Earth Metal Alkyl and Hydride Comple-xes Stabilized by a Cyclen-Derived [NNNN] Macrocyclic Ancillary Ligand. J. Am. Chem. Soc.,2008,130(22):6920-6921
[5]Roof I P, Mark D S, Park S, et al.. EuKNaTaO5:Crystal Growth, Structure and Photolumi-nescence Property. J. Am. Chem. Soc.,2009,131(12):4202-4203
[6]Ohashi M, Konkol M, Rosal I D. Rare-Earth Metal Alkyl and Hydride Complexes Stabilized by a Cyclen-Derived [NNN'N'] Macrocyclic Ancillary Ligand Romuald Poteau, Laurent Maron and Jun Okuda. J. Am. Chem. Soc.,2008, 130(22):6920-6921
[7]Felipe G, Enrique G P, Marta I, et al.. Isolated Hexanuclear Hydroxo Lanthanide Secondary Building Units in a Rare-Earth Polymeric Framework Based on p-Sulfonatocalix[4] arene. Crystal Growth and Design,2010,10(1):128-134
[8]Wang J W, Tanner P A. Upconversion for White Light Generation by a Single Compound. J. A. C. S.,2010,132:947-949
[9]Weidenthaler C, Pommerin A, Felderhoff M, et al.. Complex Rare-Earth Aluminum Hydrides:Mechanochemical Preparation, Crystal Structure and Potential for Hydrogen Sto- rage. J. A. C. S.,2009,131:16735-16743
[10]Zhang Z J, Xu X P, Li W Y, et al.. Synthesis of Rare-Earth Metal Amides Bearing an Imidazolidine-Bridged Bis (phenolato) Ligand and Their Application in the Polymerization of L-Lactide. Inorg. Chem.,2009,48:5715-5724
[11]Gerd W R, Florian A R, Mei Z P, et al.. Flexible Coordination Mode of a Donor Functionalized Terphenyl Ligand in Monomeric Cp-Based Lanthanocenes. Organometallics,2009,28:5277-5280
[12]郭栋才,张为,舒万艮,等.铽芳香羧酸丙烯酰胺三元配合物的合成及发光性能研究.稀土,2006,27(2)：22-29
[13]刘胜利,黄莉,禹良才,等.对三氟甲基苯甲酸和2,2-联吡啶双核铽配合物的合成、晶体结构及发光性质.无机化学学报,2009,25(6)：1102-1105
[14]江艳华,秦玉升,乔立军,等.稀土三元催化剂下正辛酸缩水甘油酯-二氧化碳-环氧丙烷的三元共聚合.应用化学,2009,26(7)：770-774
[15]Wessman S I. Intramolecular energy transfer the fluorescence of complexes of europium. Chem. Phys.,1942,10(4):214-217
[16]Crosby G A, Whan R E, Alire R M. Intramolecular energy transfer in rare earth chelates. Chem. Phys.,1961,34(3):734-738
[17]Susumu S, Masanobu W. Relations between intramolecular energy transfer effici-encies and triplet state energies in rare earth β-diketone chelates. Bull. Chem. Soc. Jpn.,1970,43(7):1955
[18]李建宇.稀土发光材料及其应用.北京：化学工业出版社,2004,2
[19]Liu D, Wang Z G, Yu H, et al.. Fluorescence properties of novel rare earth com-plexes using carboxyl-containing polyaryletherketones as macromolecular ligands. European Polymer Journal,2009,45:2260-2268
[20]Silversmith A J, Nguyen T T, Campbell D L, et al.. Fluorescence yield in rare ear-th doped sol-gel silicate glasses. Journal of Luminescence,2009,129:1501-1504
[21]Bernard M, Lena B, Patrick G, et al.. Research of green emitting rare-earth doped materials as potential quantum-cutter. Optical Materials,2008,30:1083-1087
[22]Klauth P, Joschko A, Ustohal P, et al.. Light fiber optic probe for measuring internal breakthrough of rare earth ionlabelled microspheres in porous media under unsaturated conditions. Colloids and Surfaces A:Physicochem. and Eng. Asp-ects,2008,325:173-179
[23]Ashokan A, Menon D, Nair S, et al.. A molecular receptor targeted, hydroxyapa-tite nanocrystal based multi-modal contrast agent. Biomaterials,2010,31: 2606-2616
[24]李昶红,郭栋才,杨颖群,等.一维链状铽配位聚合物{[Tb(p-MBA)2 (H2O)2]2·(4,4'-bidy)2}n的合成、晶体结构及荧光分析.无机化学学报,2006,22(11)：2085-2089
[25]郭栋才,苟丽宁,周悦,等.铕-芳香羧酸-丁二酸三元配合物的合成及荧光性能研究.材料研究学报,2009,23(3)：257-263
[26]Kido J, Nagai K, Ychashi. Electroluminescence in terbium complex. Chem. Lett, 1990,22(7):657-660
[27]Kwon Y S, Jung M H, Lee K R, et al.. Correlation of an infrared absorption with carriers in rare-earth monoantimonides. Physica B:Condensed Matter,1997, 240(1-2):88-91
[28]Kido J, Hayase H. Bright and light-emitting organic electroluminescent devices having an europium complex as an emitter. Appl. Phys. Lett,1994,65(17): 2124-2126
[29]Martinez A, Zenteno L A, Kuo J C K. Analysis of the fluorescence decay of MCVD Nd Al-codoped SiO2 fiber-preforms prepared by rare-earth chelate delivery. Optics Communications,1999,160(4-6):235-239
[30]Collins J M, Bartolo B D. Temperature and energy gap dependence of energy transfer between rare-earth ions in solids. Journal of Luminescence,1996, 69(5-6):335-341
[31]Balzali J C G., Murner H R, Chassat E, et al.. Strong enhancement of the lanthani-de-centred luminescence in complexes with 4-alkylated 2,2';6',2"-terpyridines. Dalton Trans.,2000,2809-2816
[32]Siddall T H. Effects of Structure of N,N-Disubstituted Amides on their Extraction of Actinide and Zirconium Nitrates and of Nitric Acid. J. Phys. Chem.,1960,64: 1863
[33]Norbert N L, Robert K, Funck J J, et al.. Extraction von Alkali-und Erdalkalimetall pikraten auswasscrigen Losungen in Methylenchlorid durch ungeladene zayklische Ionophoren Quantitat Interpretation. Helvetica Chimica, Acta,1978,61(190):2019-2039
[34]Schefer U, Ammann D, Pretsch E, et al.. Neutral Carrier Bassed Ca2+-Slectrode Electrode with Detection Limit in the Sub-Nanomolar Range. Anal. Chem.,1986, 58:2282-2285
[35]Narita H, Yaita T, Tamura K, et al.. Solvent Extraction of Trivant Lathanoid Ions With N,N-Dimethyl-N,N'-Diphenl-3-Oxapenatanediamide. Radiochim. Acta.,1998,81:223-226
[36]孙国新,韩景田,李玉兰,等.N,N,N’,N’-四已基丙二酰胺从硝酸介质中萃取铀(Ⅵ).应用化学,1998,15(4)：29-32
[37]康文,刘峙嵘,李传茂,等.萃取剂N-正丁基二乙酰亚胺的合成及其对铈(Ⅳ)的萃取行为.稀土,2006,27(3)：57-60
[38]Piguet C, Bulnzli J C G, Bernardinelli G, et al.. Lanthanide Podates with Prede-termined Structural and Photophysical Properties:Strongly Luminescent Self-As-sembled Heterodinuclear d-f Complexes with a Segmental Ligand Containing Heterocyclic Imines and Carboxamide Binding Units. J. A. C. S,1996,118: 6681-6697
[39]Gunnlaugsson T, Parker D. Luminescent europium tetraazamacrocyclic complexes with wide range pH sensitivity. Chem. Commun,1998,511-512
[40]陆晓红,林秋月,孔黎春,等.N,N-双(2-吡啶甲酰胺)-1,2-乙烷双核稀土配合物的合成及与DNA的相互作用.化学研究与应用,2006,12(2)：1652-1656
[41]陆晓红,林秋月,胡瑞定,等.稀土N,N’-双(2-吡啶甲酰胺)-1,2-乙烷配合物合成及与DNA的作用.光谱学与光谱分析,2007,27(6)：1176-1180
[42]辛红,王晓菊.聚(苯乙烯-丙烯酰胺)负载氯化钕配合物在4-乙烯吡啶聚合反应中的催化性能.稀土,2002,23(1)：35-37
[43]张雪黎,罗来涛.A位掺杂LaSrCoO4对CO和C3H8氧化性能研究.环境科学与技术,2007,30(5)：70-72
[44]Thomas B, Sugunan S. Rare catalysts-earth (Ce3+, La3+, Sm3+, and RE3+) exch-anged Na-Y zeolites and K-10 clay as solid acid for the synthesis of benzoxazole via Beckmann rearrangement of salicylaldoxime. Microporous and Mesoporous Materials,2006,96(1-3):55-64
[45]钱德胜,程广斌,吕春绪.稀土金属在离子液体中催化甲苯的硝化反应.应用化学,2009,26(7)：757-761
[46]Grigoryan H A, Hambardzumyan A A, Mkrtchyan M V, et al.. a,P-Dehydropheny-lalanine choline esters, a new class of reversible inhibitors of human acetylcholin-esteras and butyrylcholinesterase. Chemico Biological Interactions,2008: 108-116
[47]Chai J F, Liu G S, Chaicharoen K, et al.. Cobalt-Catalyzed Carbonylative Polymerization of Azetidines. Macromolecules 2008,41:8980-8985
[48]Pang X, Chu C C. Synthesis, characterization and biodegradation of functiona-lized amino acid-based poly(ester amide)s. Biomaterials.2010,31:3745-3754
[49]徐旭,伍国琳,张琳.具有乙二醇侧链的聚谷氨酸酯的合成、表征及其两亲性.化学学报,2008,66(9)：1102-1106
[50]Mansour I B, Alouani K, Chauveau E. Synthesis and characterisation of poly-(ester-amide)s from aromatic bisoxazoline precursors. European Polymer Journal, 2010,46:814-820
[51]Bruno O, Brullo C, Bondavalli F.1-Methyl and 1-(2-hydroxyalkyl)-5-(3-alkyl/cy-clo-alkyl/phenyl/naphthylureido)-1H-pyrazole-4-carboxylic acid ethyl esters as potent human neutrophil chemotaxis inhibitors. Bioorganic and Medicinal Chemi-stry,2009,17:3379-3387
[52]Sondhi S M., Singh J, Kumar A. Synthesis of amidine and amide derivatives and their evaluation for anti-inflammatory and analgesic activities. European Journal of Medicinal Chemistry,2009,44:1010-1015
[53]Huszar J, Timar Z, Szalai K K. Novel bradykinin-1 antagonists containing a (l,2,3,4-tetrahydro-isoquinolin-1-yl)acetic acid scaffold. European Journal of Medicinal Chemistry,2008,43:1552-1558
[54]Zou Y, Liu W L, Gao S. Synthesis, structure and magnetic properties of carboxy-late-bridged polynuclear copper(II)-lanthanide(III) rings:[Ln(H2O)5(CuL)2] [Cu-L]·8H2O (Ln= La, Ce). Polyhedron.2004,23:2253-2258
[55]Cerchiaro G, Aquilano K, Filomeni G, et al.. Isatin-Schiff base copper(II) comple-xes and their influence on cellular viability. Journal of Inorganic Biochemistry. 2005,99:1433-1440
[56]何水样,陈军利,杨锐,等.水杨醛水杨酰腙及其稀土配合物的合成、波谱研究及生物活性.有机化学,2003,23(12)：1387-1392
[57]Harvey R G., Dai Q, Ran C Z. Regioselective arylation of 2'-deoxyribonucleo-sides on amido or imino sites by copper(II)-mediated direct coupling with aryl-boronic acids. Tetrahedron 2006,62:1764-1771
[58]Wang Q M, Yan B. Molecular assembly and photophysical properties of a novel luminescent terbium hybrid material with modified carboxyl group of P-amino-benzoic acid as a functional bridge. Materials Letters,2006,60:3420-3425
[59]Duan G J, Yang Y, Liu T H, et al.. Synthesis, characterization of the luminescent lanthanide complexes with (Z)-4-(4-methoxyphenoxy)-4-oxobut-2-enoic acid. Spectrochimica Acta Part A,2008,69:427-431
[60]Liu T, Duan G J, Zhang Y P, et al.. Synthesis and characterization of the luminescent lanthanide complexes with two similar benzoic acids [J]. Spectroch-imica Acta Part A,2009,74:843-848
[61]Shoko S, Hiroshi F, Yasuo Y, et al.. Asymmetric fluorination of b-keto esters catalyzed by chiral rare earth perfluorinated organophosphates Tetrahedron: Asymmetry,2006,175:504-507
[62]Nakayama Y, Sasaki K, Watanabe N, et al.. Ring-opening polymerization of six-membered cyclic esters catalyzed by tetrahydroborate complexes of rare earth metals. Polymer,2009,50 (20):4788-4793
[63]Merce A, Xavier R, Josep M S, et al.. A study of the degradation of ester-modified epoxy resins obtained by cationic copolymerization of DGEBA with y-lactones initiated by rare earth triflates. Polymer Degradation and Stability,2007,92(12): 2214-2222
[64]Geary W J. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coordination Chemistry Reviews, 1971,7(1):81-122
[65]黄量,于德全.紫外光谱在有机化学中的应用.北京：科学出版社,2000,12-16.
[66]郭栋才,王鑫,谭慧,等.铕-邻菲咯啉衍生物-脂肪酸配合物的合成及性能.中国有色金属学报,2008,18(11)：2111-2117
[67]Nakamato K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. New York:Hohn Wilry,1978,227-248
[68]Barbara P F, Rentzepis P M, Brus L E. Photochemical Kinetics of Salicylidenaniline. J. A. C. S.,1980,102(8):2786-2791
[69]Wu S L, Wu Y L, Yang Y S. Rare earth (Ⅲ) complexes with indole-derived acetylacetones II. luminescent intensity for europium (Ⅲ) and terbium (Ⅲ) complexes. Journal of Alloys and Compounds,1992,180(1-2):399-402
[70]Liu G F, Shi T S, Zhao Y N. Infrared and Raman spectra of complexes about rare earth nitrate with Schiff base from o-vanillin and 1-naphthylamine. Journal of Molecular Structure,1997,412(1-2):75-81
[71]Wang B D, Yang Z Y, Qin D D, et al.. Synthesis, characterization, cytotoxic activity and DNA-binding properties of the Ln (III) complexes with ethylenediiminobi (6-hydroxychromone-3-carbal dehyde) Schiff-base. Journal of Photochemistry and Photobiology A:Chemistry,2008,194(1,5):49-58
[72]Binnemans K, Deun R Van, Bruce D W, et al.. Influence of the lanthanide contraction on the transition temperatures of rare-earth containing metallom-esogens with Schiff base ligands. Chemical Physics Letters,1999,300(3-4,5): 509-514
[73]Liu Y C, Yang Z Y. Synthesis, crystal structure, antioxidation and DNA binding properties of binuclear Ho (III) complexes of Schiff-base ligands derived from 8-hydroxyquinoline-2-carboxyaldehyde and four aroylhydrazines. Journal of Organometallic Chemistry,2009,694(19):3091-3101
[74]Liu Y C, Yang Z Y. Crystal structures, antioxidation and DNA binding properties of Eu (III) complexes with Schiff-base ligands derived from 8-hydroxyquino-line-2-carboxy-aldehyde and three aroylhydrazines. Journal of Inorganic Biochemistry,2009,103(7):1014-1022
[75]Kaczmarek S M, Leniec G. Spectral and magnetic properties of macroacyclic and macrobicyclic Schiff base RE complexes. Journal of Non-Crystalline Solids,2009, 355(24-27):1325-1332
[76]Leniec G, Kaczmarek S M, Typek J, et al.. FT-IR, ESI and EPR studies of a Dy(Ⅲ) Schiff base podand complex. Journal of Non-Crystalline Solids,2009, 35(24-27):1355-1359
[77]Solomon V R, Hu C K, Lee H, et al.. Hybrid pharmacophore design and synthesis of isatin-benzothiazole analogs for their anti-breast cancer activity. Bioorganic & Medicinal Chemistry,2009,17:7585-7592
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |