新型双8-羟基喹啉配体及其锌、铝配位聚合物的合成和性能
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摘要
合成2种双8-羟基喹啉配体:3,5-二[4-(8-羟基喹啉-5-亚甲氨基)苯氧基]苯甲酸辛酯(B8HQO)和3,5-二[4-(8-羟基喹啉-5-亚甲氨基)苯氧基]苯甲酸十六酯(B8HQH),进一步与Zn(Ⅱ)、Al(Ⅲ)配位,得到4种金属配位聚合物(B8HQO-Zn、B8HQH-Zn、B8HQO-Al和B8HQH-Al)。通过元素分析、红外光谱(FIIR)、紫外可见光谱(UV-Vis)、核磁共振氢谱(~1H NMR)、电感耦合等离子体发射光谱(ICP-OES)、热重分析(TGA)及荧光光谱等测试手段对配体及金属配位聚合物进行结构表征和性能研究。结果表明,与配体B8HQO和B8HQH相比,4种配位聚合物的溶解性降低,但可部分溶于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)中。锌、铝配位聚合物的5%失重温度分别在378和364℃附近,具有较好的热稳定性。4种配位聚合物的DMF溶液(3×10~(-5)mol/L)在478~502 nm发射绿色荧光,荧光量子效率28%~37%,固体在528~553 nm发射强绿色荧光,具有良好的发光性能。
Two novel ligands,3,5-bis( 4-( 8-hydroxyquinoline-5-methyleneamino) phenoxy) octyl benzoate( B8 HQO) and 3,5-bis( 4-( 8-hydroxyquinoline-5-methyleneamino) phenoxy) hexadecyl benzoate( B8 HQH)were synthesized and coordinated with Zn(Ⅱ) and Al( Ⅲ), respectively, to get the four corresponding coordination polymers( B8 HQO-Zn,B8 HQH-Zn,B8 HQO-Al and B8 HQH-Al). Their structures and properties were characterized by elemental analysis, Fourier transform infrared spectrometer( FTIR), UV-visible absorption( UV-Vis),proton nuclear magnetic resonance spectroscopy(1 H NMR),inductively coupled plasma optical emission spectroscopy( ICP-OES),thermal gravimetric analyzer( TGA) and fluorescence spectroscopy.The results indicate that compared with B8 HQO and B8 HQH,the solubility of the four coordination polymers is reduced,but can be partially soluble in N,N-dimethyl formamide( DMF),N,N-dimethyl acetamide( DMAC),dimethylsulfone( DMSO),N-methylpyrrolidone( NMP). The 5% mass loss temperatures of zinc and aluminum coordination polymers at around 378 and 364 ℃,respectively,show that they have good thermal stability. The fluorescence measurement shows that they emit green luminescence at 478 ~ 502 nm in DMF solution( 3 × 10~(-5) mol/L) and their fluorescence quantum efficiency is 28% ~ 37%. The four coordination polymers emitting strong green luminescence at 528 ~ 553 nm in the solid state show that they have good luminescent properties.
Two novel ligands,3,5-bis( 4-( 8-hydroxyquinoline-5-methyleneamino) phenoxy) octyl benzoate( B8 HQO) and 3,5-bis( 4-( 8-hydroxyquinoline-5-methyleneamino) phenoxy) hexadecyl benzoate( B8 HQH)were synthesized and coordinated with Zn(Ⅱ) and Al( Ⅲ), respectively, to get the four corresponding coordination polymers( B8 HQO-Zn,B8 HQH-Zn,B8 HQO-Al and B8 HQH-Al). Their structures and properties were characterized by elemental analysis, Fourier transform infrared spectrometer( FTIR), UV-visible absorption( UV-Vis),proton nuclear magnetic resonance spectroscopy(1 H NMR),inductively coupled plasma optical emission spectroscopy( ICP-OES),thermal gravimetric analyzer( TGA) and fluorescence spectroscopy.The results indicate that compared with B8 HQO and B8 HQH,the solubility of the four coordination polymers is reduced,but can be partially soluble in N,N-dimethyl formamide( DMF),N,N-dimethyl acetamide( DMAC),dimethylsulfone( DMSO),N-methylpyrrolidone( NMP). The 5% mass loss temperatures of zinc and aluminum coordination polymers at around 378 and 364 ℃,respectively,show that they have good thermal stability. The fluorescence measurement shows that they emit green luminescence at 478 ~ 502 nm in DMF solution( 3 × 10~(-5) mol/L) and their fluorescence quantum efficiency is 28% ~ 37%. The four coordination polymers emitting strong green luminescence at 528 ~ 553 nm in the solid state show that they have good luminescent properties.
引文
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[2]Yuan G Z,Zhang Q,Wang Z P,et al.Assembly of Four 8-Quinolinate-Based Multinuclear Complexes:The Effect of Substituents on Core Structures and Photoluminescence Properties[J].Dyes Pigm,2017,4(5):764-772.
[3]Jarzembska K N,Kaminski R,Durka K,et al.New Class of Easily-Synthesisable and Modifiable Organic Materials for Applications in Luminescent Devices[J].Dyes Pigm,2017,138(1):267-277.
[4]Shamsipur M,Memari Z,Ganjali M R,et al.Highly Sensitive Gold Nanoparticles-Based Optical Sensing of DNA Hybridization Using Bis(8-hydroxyquinoline-5-solphonate)cerium(Ⅲ)Chloride as a Novel Fluorescence Probe[J].J Pharm Biomed Anal,2016,118(1):356-362.
[5]Lashgari N,Badiei A,Ziarani G M,et al.A Fluorescent Sensor for Al(Ⅲ)and Colorimetric Sensor for Fe(Ⅲ)and Fe(Ⅱ)Based on a Novel 8-Hydroxyquinoline Derivative[J].J Fluoresc,2016,5(1):1885-1894.
[6]Gao R,Niu G D,Wang L D,et al.Interface Modification of 8-Hydroxyquinoline Aluminium with Combined Effects in Quasi-Solid Dye-Sensitized Solar Cells[J].Phys Chem Chem Phys,2012,14(17):5973-5978.
[7]Zhu C X,Peng D H,Hu J M,et al.Novel Dyes of Branched Chain Polymeric Metal Complexes with Benzodithiophene or Hydroquinone Derivatives as Donor:Synthesis,Characterization,and Photovoltaic Performance for Dye-Sensitized Solar Cells[J].Monatsh Chem,2017,148(2):217-225.
[8]Mishra A,Nayak P K,Periasamy N.Synthesis of 5-Alkoxymethyl-and 5-Aminomethyl-Substituted 8-Hydroxyquinoline Derivatives and Their Luminescent Al(Ⅲ)Complexes for OLED Applications[J].Tetrahedron Lett,2004,45(33):6265-6268.
[9]Jeong S M,Takanishi Y,Ishikawa K,et al.Sharply Directed Emission in Microcavity Organic Light-emitting Diodes with a Cholesteric Liquid Crystal Film[J].Opt Commun,2007,273(1):167-172.
[10]Shahedi Z,Jafari M R,Zolanvari A A,et al.Synthesis of Zn Q2,Ca Q2,and Cd Q2for Application in OLED:Optical,Thermal,and Electrical Characterizations[J].J Mater Sci-Mater Electron,2017,28(10):7313-7319.
[11]Chen C H,Shi J M.Metal Chelates as Emitting Materials for Organic Electroluminescence[J].Coord Chem Rev,1998,171(1):161-174.
[12]LIU Dan,WANG Zhonggang.Preparation and Fluorescence Properties of Samarium Complexes Containing Polyaryletherketones Bearing Pendant Carboxyl Groups[J].Acta Polym Sin,2010,5(1):567-573(in Chinese).刘丹,王忠刚.含羧基侧基聚芳醚酮-钐配位聚合物的制备及其荧光性能研究[J].高分子学报,2010,5(1):567-573.
[13]Camerel F,Barbera J,Otsuki J,et al.Solution-Processable Liquid Crystals of Luminescent Aluminum(8-Hydroxyquinoline-5-Sulfonato)Complexes[J].Adv Mater,2008,20(18):3462-3467.
[14]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,2017,34(3):338-344(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.
[15]Modiri S,Mohseni M,Mohajerani E,et al.Photo and Electroluminescence of a Solution Processable Silane Modified Alq3Composite Showing Bluish Green Emission[J].J Mater Sci-Mater Electron,2015,26(6):3649-3656.
[16]Li S J,Li Y,Zhang J A.Synthesis and Performances of a Tridentate 8-Hydroxyquinoline Derivative Ligand and Its Zinc Complex[J].Inorg Chem Commun,2012,20(1):334-339.
[17]Toiserkani H.Synthesis and Evaluation of Properties of Novel Aromatic Poly(Ether-Imide)with Benzazole Pendent Groups and Flexible Ether Linkages[J].High Perform Polym,2011,23(7):542-554.
[18]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.
[19]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.
[20]He Y,Zhong C F,He A H,et al.Synthesis and Luminescent Properties of Novel Bisfunctional Polymeric Complexes Based on Carbazole and 8-Hydroxyquinoline Groups[J].Mater Chem Phys,2009,114(1):261-266.
[21]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.