含8-羟基喹啉侧基聚酯及其锌和铝配合物的合成与荧光性质
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摘要
经多步反应合成3种含8-羟基喹啉侧基聚酯(P7～P9),进一步与无水醋酸锌和六水氯化铝反应,得到6种聚酯锌、铝配合物(P7-Zn～P9-Zn,P7-Al～P9-Al)。采用元素分析、红外光谱、紫外可见光谱、核磁共振氢谱、凝胶渗透色谱、热重分析仪、差示扫描量热和荧光光谱等技术手段对其结构和性能进行表征。P7～P9易溶于N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺(DMAC)、二甲基亚砜(DMSO)和N-甲基吡咯烷酮(NMP),P7-Zn～P9-Zn和P7-Al～P9-Al部分溶于DMF、DMAC、DMSO和NMP。P7～P9的质均相对分子质量(Mw)为1. 79×10~4、2. 14×10~4和2. 52×10~4g/mol,相对分子质量分布指数PDI为1. 54、1. 64和1. 72。P7～P9的5%失重温度分别为291. 6、291. 3和284. 9℃,P7-Zn～P9-Zn、P7-Al～P9-Al的5%失重温度分别为348. 7、339. 2、334. 6、316. 1、316. 7和316. 0℃。P7～P9的玻璃化转变温度(T_g)分别为121. 8、106. 2和86. 4℃,聚酯锌、铝配合物的T_g均高于180℃。P7～P9的DMF溶液(5×10~(-5)mol/L)在413～418 nm处发紫色荧光,P7-Zn～P9-Zn、P7-Al～P9-Al的DMF溶液(5×10~(-5)mol/L)分别在509～513和485～487 nm处发强绿色荧光,固体分别在516～519和492～497 nm处发强绿色荧光。P7～P9、P7-Zn～P9-Zn和P7-Al～P9-Al的荧光量子产率分别为5. 5%～8. 4%、21%～28%和23%～29%。
Three kinds of novel polyesters containing 8-hydroxyquinoline side groups( P7 ～ P9) were synthesized,and subsequently their zinc complexes( P7-Zn ～ P9-Zn) and aluminum complexes( P7-Al ～P9-Al) were obtained by reactions with zinc acetate and aluminum chloride,respectively. The structures and properties of polyesters and their metal complexes were characterized by elemental analysis,infrared( IR),ultraviolet-visable spectroscopy( UV-Vis),proton nuclear magnetic resonance(1 H NMR),gel permeation chromatography( GPC), thermogravimetric analysis( TG), differential scanning calorimetry( DSC) and fluorescence spectroscopy. The polyesters obtained are soluble in N,N-dimethyl formamide( DMF),N,Ndimethyl acetamide( DMAC),dimethylsulfoxide( DMSO),and N-methyl pyrrolidone( NMP). Complexes P7-Zn ～ P9-Zn and P7-Al ～ P9-Al can be partially dissolved in DMF,DMAC,DMSO and NMP. The Mwand polydispersity index( PDI) of P7 ～ P9 are 1. 79 × 10~4,2. 14 × 10~4 and 2. 52 × 10~4 g/mol and 1. 54,1. 64 and1. 72,respectively. The 5% mass loss temperatures of P7 ～ P9,P7-Zn ～ P9-Zn and P7-Al ～ P9-Al are291. 6,291. 3,284. 9,348. 7,339. 2,334. 6,316. 1,316. 7 and 316. 0 ℃,respectively. The glass transition temperatures( T_g) of P7 ～ P9 are 121. 8,106. 2 and 91. 3 ℃,respectively,and T_gof their metal complexes are all higher than 180 ℃. Fluorescence emission peaks of P7 ～ P9 in DMF solution appear at413 ～ 418 nm,emitting weak purple light. Fluorescence emission peaks of P7-Zn ～ P9-Zn and P7-Al ～ P9-Al in DMF solution emerged at 509 ～ 513 and 485 ～ 487 nm,respectively,emitting strong green light,Fluorescence emission peaks of P7-Zn ～ P9-Zn and P7-Al ～ P9-Al in solid state located at 516 ～ 519 and492 ～ 497 nm,respectively,emitting strong green light. The fluorescence quantum yields of P7 ～ P9,P7-Zn ～ P9-Zn and P7-Al ～ P9-Al are 5. 5% ～ 8. 4%,21% ～ 28% and 23% ～ 29%,respectively.
Three kinds of novel polyesters containing 8-hydroxyquinoline side groups( P7 ～ P9) were synthesized,and subsequently their zinc complexes( P7-Zn ～ P9-Zn) and aluminum complexes( P7-Al ～P9-Al) were obtained by reactions with zinc acetate and aluminum chloride,respectively. The structures and properties of polyesters and their metal complexes were characterized by elemental analysis,infrared( IR),ultraviolet-visable spectroscopy( UV-Vis),proton nuclear magnetic resonance(1 H NMR),gel permeation chromatography( GPC), thermogravimetric analysis( TG), differential scanning calorimetry( DSC) and fluorescence spectroscopy. The polyesters obtained are soluble in N,N-dimethyl formamide( DMF),N,Ndimethyl acetamide( DMAC),dimethylsulfoxide( DMSO),and N-methyl pyrrolidone( NMP). Complexes P7-Zn ～ P9-Zn and P7-Al ～ P9-Al can be partially dissolved in DMF,DMAC,DMSO and NMP. The Mwand polydispersity index( PDI) of P7 ～ P9 are 1. 79 × 10~4,2. 14 × 10~4 and 2. 52 × 10~4 g/mol and 1. 54,1. 64 and1. 72,respectively. The 5% mass loss temperatures of P7 ～ P9,P7-Zn ～ P9-Zn and P7-Al ～ P9-Al are291. 6,291. 3,284. 9,348. 7,339. 2,334. 6,316. 1,316. 7 and 316. 0 ℃,respectively. The glass transition temperatures( T_g) of P7 ～ P9 are 121. 8,106. 2 and 91. 3 ℃,respectively,and T_gof their metal complexes are all higher than 180 ℃. Fluorescence emission peaks of P7 ～ P9 in DMF solution appear at413 ～ 418 nm,emitting weak purple light. Fluorescence emission peaks of P7-Zn ～ P9-Zn and P7-Al ～ P9-Al in DMF solution emerged at 509 ～ 513 and 485 ～ 487 nm,respectively,emitting strong green light,Fluorescence emission peaks of P7-Zn ～ P9-Zn and P7-Al ～ P9-Al in solid state located at 516 ～ 519 and492 ～ 497 nm,respectively,emitting strong green light. The fluorescence quantum yields of P7 ～ P9,P7-Zn ～ P9-Zn and P7-Al ～ P9-Al are 5. 5% ～ 8. 4%,21% ～ 28% and 23% ～ 29%,respectively.
引文
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[9]Chen X,Liao Y,Liu Y,et al. Dye Sensitizers of Polymer Using the Complex of Cd(Ⅱ)or Cu(Ⅱ)with Imidazole as Auxiliary Electron Acceptor for Dye-Sensitized Solar Cells[J]. Dyes Pigm,2017,139:420-430.
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[11]Xiao L F,Liu Y,Xiu Q,et al. Novel Polymeric Metal Complexes as Dye Sensitizers for Dye-Sensitized Solar Cells Based on Poly Thiophene Containing Complexes of 8-Hydroxyquinoline with Zn(Ⅱ),Cu(Ⅱ)and Eu(Ⅲ)in the Side Chain[J].Tetrahedron,2010,66(15):2835-2842.
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[13]Cao D K,Liu B,Gu Y W,et al. Phosphonates Containing 8-Hydroxyquinoline Moiety and Their Metal Complexes:Structures,Fluorescent and Magnetic Properties[J]. Dalton Trans,2013,42(34):12228-12237.
[14]Fazaeli Y,Amini M M,Najafi E,et al. Synthesis and Characterization of 8-Hydroxyquinoline Complexes of Tin(Ⅳ)and Their Application in Organic Light Emitting Diode[J]. J Fluoresc,2012,22(5):1263-1270.
[15]Chen C H,Shi J M. Metal Chelates as Emitting Materials for Organic Electroluminescence[J]. Coordin Chem Rev,1998,171(1):161-174.
[16]Zhao L M,Yan B. Novel Polymer-Inorganic Hybrid Materials Fabricated with in Situ Composition and Luminescent Properties[J]. J Non-Cryst Solids,2007,353(52/54):4654-4659.
[17]Zhong C,Wu Q,Guo R,et al. Synthesis and Luminescence Properties of Polymeric Complexes of Cu(Ⅱ),Zn(Ⅱ)and Al(Ⅲ)with Functionalized Polybenzimidazole Containing 8-Hydroxyquinoline Side Group[J]. Opt Mater,2008,30(6):870-875.
[18]Luo J,Zhang C,Yang C,et al. Novel Near-Infrared Luminescent Linear Copolymer Based on Tris(8-Hydroxyquinoline)erbium[J]. Synth Met,2012,162(5/6):431-435.
[19] WU Yan,GUO Zhaonan,YU Shijun,et al. Synthesis and Properties of Polyesters Containing 8-Hydroxyquinoline Side Groups and Their Zn(Ⅱ),Al(Ⅲ)Complexes[J]. Chinese J Appl Chem,2016,33(4):452-458(in Chinese).吴岩,郭照南,于世钧,等.含8-羟基喹啉侧基聚酯及其锌、铝配合物的合成和性能[J].应用化学,2017,34(3):338-344.
[20]YU Shijun,LU Yan,WU Siyu,et al. Synthesis and Properties of Containing Schiff Base Side Groups and Their Zinc Complexes[J]. Chinese J Appl Chem,2016,33(4):452-458(in Chinese).于世钧,鲁岩,吴思雨,等.含希夫碱侧基聚酯及其锌配合物的合成和性能[J].应用化学,2016,33(4):452-458.
[21]Huang H L,Zhong C F,Zhou Y. Zn(Ⅱ)Synthesis and Luminescent Properties of Polymeric Metal Complexes Containing Bis(8-Hydroxyquinoline)Group[J]. Eur Polym J,2008,44(9):2944-2950.
[22]Deng J Y,Guo L H,Xiu Q,et al. Two Polymeric Metal Complexes Based on Polycarbazole Containing Complexes of8-Hydroxyquinoline with Zn(Ⅱ)and Ni(Ⅱ)in the Backbone:Synthesis,Characterization and Photovoltaic Applications[J]. Mater Chem Phys,2012,133(1):452-458.
[23]Du F F,Wang H,Bao Y Y,et al. Conjugated Coordination Polymers Based on 8-Hydroxyquinoline Ligands:Impact of Polyhedral Oligomeric Silsesquioxanes on Solubility and Luminescence[J]. J Mater Chem,2011,21(29):10859-10864.
[24]LIU Dan. Preparation and Fluorescence Properties of Novel Rare Earth-Coordinated Polyaryletherketone Complexes[D].Dalian:Dalian University of Technology,2010(in Chinese).刘丹.新型聚芳醚酮稀土配合物的制备及其荧光性能研究[D].大连:大连理工大学,2010.
[25]Pohl R,Monters V A,Shinar J,et al. Red-Green-Blue Emission from Tris(5-aryl-8-quinolinolate)Al(Ⅲ)Complexes[J].J Org Chem,2004,69(5):1723-1725.
[26]Hopkins T A,Meerholz K,Shaheen S,et al. Substituted Aluminum and Zinc Quinolates with Blue-Shifted Absorbance/Luminescence Bands:Synthesis and Spectroscopic,Photoluminescence,and Electroluminescence Characterization[J].Chem Mater,1996,8(2):344-351.
[27]KnippingE,Roche I U,Dufresne S,et al. Selective Fluorescence Turn-On of a Prefluorescent Azomethine with Zn2+[J].Tetrahedron Lett,2011,52(34):4385-4387.
[2]Tolkki A,Kaunisto K,Heiskanen J P,et al. Organometallic Tris(8-Hydroxyquinoline)aluminum Complexes as Buffer Layers and Dopants in Inverted Organic Solar Cells[J]. Thin Solid Films,2012,520(13):4475-4481.
[3]Chang Y F,Meng H F,Fan G L,et al. Blade Coating of Tris(8-Hydroxyquinolinato)aluminum as the Electron-Transport Layer for All-Solution Blue Fluorescent Organic Light-Emitting Diodes[J]. Org Electron,2016,29:99-106.
[4]Shi J,Gong C,Zeng X,et al. Three Multinuclear Metal-Organic Coordination Compounds Based on 8-Hydroxyquinoline Derivative:Syntheses,Structures and Fluorescence Properties[J]. Polyhedron,2015,102:562-568.
[5]Muhammad F F,Yahya M Y,Aziz F,et al. Tuning the Extinction Coefficient,Refractive Index,Dielectric Constant and Optical Conductivity of Gaq3Films for the Application of OLED Displays Technology[J]. J Mater Sci-Mater Electron,2017,28(19):14777-14786.
[6]Huang S,Pang G,Li X,et al. Nanowires of Metal(Cd,Cu)Halide Complexes with 8-Hydroxyquinoline for Photoelectrochemical and Electrochemiluminescence Sensing[J]. J Nanopart Res,2017,19(12):392.
[7]Kumar P,Misra A,Bhardwaj R,et al. Synthesis and Characterization of Some 5-Coordinated Aluminum-8-Hydroxy Quinoline Derivatives for OLED Applications[J]. Displays,2008,29(4):351-357.
[8]Shi Y L,Fu Y Q,Lu C L,et al. High Luminescence,Organic Inorganic Nanocomposite Films with Covalently Linked8-Hydroxyquinoline Anchored to Zn S Nanoparticles[J]. Dyes Pigm,2010,85(1):66-72.
[9]Chen X,Liao Y,Liu Y,et al. Dye Sensitizers of Polymer Using the Complex of Cd(Ⅱ)or Cu(Ⅱ)with Imidazole as Auxiliary Electron Acceptor for Dye-Sensitized Solar Cells[J]. Dyes Pigm,2017,139:420-430.
[10]Cao J,Liu J C,Deng W T,et al. A Novel Self-Assembly with Zinc Porphyrin Coordination Polymer for Enhanced Photocurrent Conversion in Supramolecular Solar Cells[J]. Electrochim Acta,2013,112(12):515-521.
[11]Xiao L F,Liu Y,Xiu Q,et al. Novel Polymeric Metal Complexes as Dye Sensitizers for Dye-Sensitized Solar Cells Based on Poly Thiophene Containing Complexes of 8-Hydroxyquinoline with Zn(Ⅱ),Cu(Ⅱ)and Eu(Ⅲ)in the Side Chain[J].Tetrahedron,2010,66(15):2835-2842.
[12]Park S Y,Ghosh P,Park S O,et al. Origin of Ultraweak Fluorescence of 8-Hydroxyquinoline in Water:Photoinduced Ultrafast Proton Transfer[J]. RSC Adv,2016,6(12):9812-9821.
[13]Cao D K,Liu B,Gu Y W,et al. Phosphonates Containing 8-Hydroxyquinoline Moiety and Their Metal Complexes:Structures,Fluorescent and Magnetic Properties[J]. Dalton Trans,2013,42(34):12228-12237.
[14]Fazaeli Y,Amini M M,Najafi E,et al. Synthesis and Characterization of 8-Hydroxyquinoline Complexes of Tin(Ⅳ)and Their Application in Organic Light Emitting Diode[J]. J Fluoresc,2012,22(5):1263-1270.
[15]Chen C H,Shi J M. Metal Chelates as Emitting Materials for Organic Electroluminescence[J]. Coordin Chem Rev,1998,171(1):161-174.
[16]Zhao L M,Yan B. Novel Polymer-Inorganic Hybrid Materials Fabricated with in Situ Composition and Luminescent Properties[J]. J Non-Cryst Solids,2007,353(52/54):4654-4659.
[17]Zhong C,Wu Q,Guo R,et al. Synthesis and Luminescence Properties of Polymeric Complexes of Cu(Ⅱ),Zn(Ⅱ)and Al(Ⅲ)with Functionalized Polybenzimidazole Containing 8-Hydroxyquinoline Side Group[J]. Opt Mater,2008,30(6):870-875.
[18]Luo J,Zhang C,Yang C,et al. Novel Near-Infrared Luminescent Linear Copolymer Based on Tris(8-Hydroxyquinoline)erbium[J]. Synth Met,2012,162(5/6):431-435.
[19] WU Yan,GUO Zhaonan,YU Shijun,et al. Synthesis and Properties of Polyesters Containing 8-Hydroxyquinoline Side Groups and Their Zn(Ⅱ),Al(Ⅲ)Complexes[J]. Chinese J Appl Chem,2016,33(4):452-458(in Chinese).吴岩,郭照南,于世钧,等.含8-羟基喹啉侧基聚酯及其锌、铝配合物的合成和性能[J].应用化学,2017,34(3):338-344.
[20]YU Shijun,LU Yan,WU Siyu,et al. Synthesis and Properties of Containing Schiff Base Side Groups and Their Zinc Complexes[J]. Chinese J Appl Chem,2016,33(4):452-458(in Chinese).于世钧,鲁岩,吴思雨,等.含希夫碱侧基聚酯及其锌配合物的合成和性能[J].应用化学,2016,33(4):452-458.
[21]Huang H L,Zhong C F,Zhou Y. Zn(Ⅱ)Synthesis and Luminescent Properties of Polymeric Metal Complexes Containing Bis(8-Hydroxyquinoline)Group[J]. Eur Polym J,2008,44(9):2944-2950.
[22]Deng J Y,Guo L H,Xiu Q,et al. Two Polymeric Metal Complexes Based on Polycarbazole Containing Complexes of8-Hydroxyquinoline with Zn(Ⅱ)and Ni(Ⅱ)in the Backbone:Synthesis,Characterization and Photovoltaic Applications[J]. Mater Chem Phys,2012,133(1):452-458.
[23]Du F F,Wang H,Bao Y Y,et al. Conjugated Coordination Polymers Based on 8-Hydroxyquinoline Ligands:Impact of Polyhedral Oligomeric Silsesquioxanes on Solubility and Luminescence[J]. J Mater Chem,2011,21(29):10859-10864.
[24]LIU Dan. Preparation and Fluorescence Properties of Novel Rare Earth-Coordinated Polyaryletherketone Complexes[D].Dalian:Dalian University of Technology,2010(in Chinese).刘丹.新型聚芳醚酮稀土配合物的制备及其荧光性能研究[D].大连:大连理工大学,2010.
[25]Pohl R,Monters V A,Shinar J,et al. Red-Green-Blue Emission from Tris(5-aryl-8-quinolinolate)Al(Ⅲ)Complexes[J].J Org Chem,2004,69(5):1723-1725.
[26]Hopkins T A,Meerholz K,Shaheen S,et al. Substituted Aluminum and Zinc Quinolates with Blue-Shifted Absorbance/Luminescence Bands:Synthesis and Spectroscopic,Photoluminescence,and Electroluminescence Characterization[J].Chem Mater,1996,8(2):344-351.
[27]KnippingE,Roche I U,Dufresne S,et al. Selective Fluorescence Turn-On of a Prefluorescent Azomethine with Zn2+[J].Tetrahedron Lett,2011,52(34):4385-4387.