一种四苯基乙烯-咔唑化合物的合成与光谱性能研究
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摘要
以化合物(3,5-二(9H-咔唑-9-基)苯基)(对甲苯基)甲酮为反应物,通过McMurry偶联反应合成了一种具有四苯基乙烯-咔唑共轭结构的化合物—1,2-二(3,5-二(9H-咔唑-9-基)苯基)-1,2-二-对-芳基乙烯(BDCPDT)。通过核磁共振、元素分析和质谱等方法表征了化合物的结构;利用量子化学计算法研究了分子的几何构型和轨道分布;通过紫外吸收光谱和荧光光谱表征了化合物的光物理性质;研究结果表明:化合物是以四苯基乙烯为核心,咔唑为外围基团的螺旋桨状结构,并且具有良好的聚集诱导发光(AIE)性能,它的固体荧光发射波长为428nm,是一种蓝色发光材料。
The compound 1,2-bis(3,5-di(9 H-carbazol-9-yl)phenyl)-1,2-di-p-tolylethene(BDCPDT)with a tetraphenylethylene-carbazole conjugated structure was synthesized by the McMurry coupling reaction of compound(3,5-bis(9 H-carbazol-9-yl)phenyl)(p-tolyl)methanone.The structure of this molecule was characterized by proton NMR spectroscopy,elemental analysis and Mass spectrometry.The geometric structure and orbital distribution of the molecule were studied by quantum chemistry calculation.The photophysical properties of the compound were characterized by UV-vis absorption spectroscopy and fluorescence spectra.The results indicated that the compound(BDCPDT)show a propeller-like structure with tetraphenylethylene as the core framework and carbazole as the peripheral groups.The compound is a blue material with aggregation induced emission(AIE)property and its maximum emission wavelength is 428 nm in film.
The compound 1,2-bis(3,5-di(9 H-carbazol-9-yl)phenyl)-1,2-di-p-tolylethene(BDCPDT)with a tetraphenylethylene-carbazole conjugated structure was synthesized by the McMurry coupling reaction of compound(3,5-bis(9 H-carbazol-9-yl)phenyl)(p-tolyl)methanone.The structure of this molecule was characterized by proton NMR spectroscopy,elemental analysis and Mass spectrometry.The geometric structure and orbital distribution of the molecule were studied by quantum chemistry calculation.The photophysical properties of the compound were characterized by UV-vis absorption spectroscopy and fluorescence spectra.The results indicated that the compound(BDCPDT)show a propeller-like structure with tetraphenylethylene as the core framework and carbazole as the peripheral groups.The compound is a blue material with aggregation induced emission(AIE)property and its maximum emission wavelength is 428 nm in film.
引文
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[29]Shi H,Wang S,Fang L,et al.Synthesis,Aggregation-induced Emission and Electroluminescence Properties of Two New Tetraphenylethene Derivatives[J].Tetrahedron Lett,2016,57:4428-4434.DOI:10.1016/j.tetlet.2016.08.072.
[30]Shi H,Li M,Xin D,et al.Two Novel Phenylethene-Carbazole Derivatives Containing Dimesitylboron Groups:Aggregation-induced Emission and Electroluminescence Properties[J].Dyes Pigm,2016,128:304-313.DOI:10.1016/j.dyepig.2016.01.028.
[31]Volyniuk D,Sutaite J,Tomkeviciene A,et al.Organic Light-emitting Diodes Exploiting Aggregation-induced Exciton and Exciplex Emissions[J].J Lumin,2017,192:534-540.DOI:10.1016/j.jlumin.2017.07.040.
[32]Tomkeviciene A,Sutaite J,Volyniuk D,et al.Aggregation-induced Emission Enhancement in Charge-transporting Derivatives of Carbazole and Tetra(tri)phenylethylene[J].Dyes Pigm,2017,140:363-374.DOI:10.1016/j.dyepig.2017.01.056.
[33]Cai Y,Shi C,Zhang H,et al.Sulfur-bridged Tetraphenylethylene AIEgens for Deep-blue Organic Light-emitting Diodes[J].J Mater Chem C,2018,6:6534-6542.DOI:10.1039/c8tc01509k.
[2]Zhang L M,Li B.A Series of Eu(Ⅲ)Emitters with a Novel Triphenylamine-derived Beta-diketone Ligand[J].J Lumin,2009,129:1304-1308.DOI:10.1016/j.jlumin.2009.06.015.
[3]Kawamura Y,Brooks J,Brown J J,et al.Intermolecular Interaction and a Concentration-quenching Mechanism of Phosphorescent Ir(Ⅲ)Complexes in a Solid Film[J].Phys Rev Lett,2006,96:0174041-0174044.DOI:10.1103/PhysRevLett.96.017404.
[4]Zhang Y Q,Zhong G Y,Cao X A.Concentration Quenching of Electroluminescence in Neat Ir(ppy)3Organic Light-Emitting Diodes[J].J Appl Phys,2010,108:083107-083111.DOI:10.1063/1.3504599.
[5]Luo J D,Xie Z L,Lam J W,et al.Aggregation-induced Emission of 1-Methyl-1,2,3,4,5-Pentaphenylsilole[J].Chem Commun,2001:1740-1741.DOI:10.1039/B105159H.
[6]Hu G R,Leung Nelson L C,Tang B Z.AIE Macromolecules:Syntheses,Structures and Functionalities[J].Chem Soc Rev,2014,43:4494-4562.DOI:10.1039/c4cs00044g.
[7]Aldred M P,Li C,Zhang G F,et al.Fluorescence Quenching and Enhancement of Vitrifiable Oligofluorenes End-capped with Tetraphenylethene[J].J Mater Chem,2012,22:7515-7528.DOI:10.1039/c2jm30261f.
[8]Zhang G F,Aldred M P,Gong W L,et al.Utilising Tetraphenylethene as a Dual Activator for Intramolecular Charge Transfer and Aggregation Induced Emission[J].Chem Commun,2012,48:7711-7713.DOI:10.1039/c2cc33218c.
[9]Li C,Gong W L,Hu Z,et al.Photoswitchable Aggregation-induced Emission of a Dithienylethene-Tetraphenylethene Conjugate for Optical Memory and Super-resolution Imaging[J].RSC Adv,2013,3:8967-8972.DOI:10.1039/c3ra40674a.
[10]Wang C,Xu B J,Li M S,et al.A Stable Tetraphenylethene Derivative:Aggregation-induced Emission,Different Crystalline Polymorphs,and Totally Different Mechanoluminescence Properties[J].Mater Horiz,2016,3:220-225.DOI:10.1039/C6MH00025H.
[11]Jadhav T,Dhokale B,Mobin S M,et al.Aggregation Induced Emission and Mechanochromism in Pyrenoimidazoles[J].JMater Chem C,2015,3:9981-9988.DOI:10.1039/C5TC02181B.
[12]Jadhav T,Dhokale B,Mobin S M,et al.Mechanochromism and Aggregation Induced Emission in Benzothiazole Substituted Tetraphenylethylenes:a Structure Function Correlation[J].RSC Adv,2015,5:29878-29884.DOI:10.1039/C5RA04881H.
[13]Li H K,Zheng X Y,Su H M,et al.Synthesis,Optical Properties,and Helical Self-assembly of a Bivaline-containing Tetraphenylethene[J].Sci Rep,2016,6:19277.DOI:10.1038/srep19277(2016).
[14]Jadhav T,Dhokale B,Misra R,et al.Effect of The Cyano Group on Solid State Photophysical Behavior of Tetraphenylethene Substituted Benzothiadiazoles[J].J Mater Chem C,2015,3:9063-9068.DOI:10.1039/C5TC01871D.
[15]Jadhav T,Dhokale B,Patil Y,et al.Aggregation Induced Emission and Mechanochromism in Tetraphenylethene Substituted Pyrazabole[J].RSC Adv,2015,5:68187-68191.DOI:10.1039/C5RA12697E.
[16]Zhao Y Y,Kwok R T K,Lam J W Y,et al.A Highly Fluorescent AIE-active Theranostic Agent with Anti-tumor Activity to Specific Cancer Cells[J].Nanoscale,2016,8:12520-12523.DOI:10.1039/C5NR08782A.
[17]Lin G W,Peng H R,Chen L,et al.Improving Electron Mobility of Tetraphenylethene-based AIEgens to Fabricate Nondoped Organic Light-emitting Diodes with Remarkably High Luminance and Efficiency[J].ACS Appl Mater Interfaces,2016,8:16799-16808.DOI:10.1021/acsami.6b04924.
[18]Meunmart D,Prachumrak N,Keawin T,et al.Bis(4-diphenylaminophenyl)carbazole End-capped Fluorene as Solutionprocessed Deep-blue Light-emitting and Hole-transporting Materials for Electroluminescent Devices[J].Tetrahedron Lett,2012,53:3615-3618.DOI:10.1016/j.tetlet.2012.05.030.
[19]Yang S X,Guan D H,Yang M X,et al.Synthesis and Characterization of Novel Butterfly-shaped Aryl-substituted Indolo[2,3-a]carbazole Derivatives[J].Tetrahedron Lett,2015,56:2223-2227.DOI:10.1016/j.tetlet.2015.03.058.
[20]Liu Y,Ye X,Liu G F,et al.Structural Features and Optical Properties of a Carbazole-containing Ethene as a Highly Emissive Organic Solid[J].J Mater Chem C,2014,2:1004-1009.DOI:10.1039/C3TC32145B.
[21]Cha S W,Jin J I.A Field-dependent Organic LED Consisting of Two New High Tg Blue Light Emitting Organic Layers:a Possibility of Attainment of a White Light Sources[J].J Mater Chem,2003,13:479-484.DOI:10.1039/B209949G.
[22]Zhao Z J,Chen S M,Deng C M,et al.Construction of Efficient Solid Emitters with Conventional and AIE Luminogens for Blue Organic Light-emitting Diodes[J].J Mater Chem,2011,21:10949-10956.DOI:10.1039/C1JM10221D.
[23]Zhao Z J,Chen S M,Lam J W Y,et al.Creation of Highly Efficient Solid Emitter by Decorating Pyrene Core with AIE-active Tetraphenylethene Peripheries[J].Chem Commun,2010,46:2221-2223.DOI:10.1039/b921451h.
[24]Li J Y,Duan Y H,Li Q,et al.Novel Thieno-[3,4-b]-pyrazine Derivatives for Non-doped Red Organic Light-emitting Diodes[J].Dyes Pigm,2013,96:391-396.DOI:10.1016/j.dyepig.2012.08.028.
[25]Huang J,Yang X,Wang J Y,et al.New Tetraphenylethene-based Efficient Blue Luminophors:Aggregation Induced E-mission and Partially Controllable Emitting Color[J].J Mater Chem,2012,22:2478-2484.DOI:10.1039/c1jm14054j.
[26]Zhao Z J,Chan C Y K,Chen S M,et al.Using Tetraphenylethene and Carbazole to Create Efficient Luminophores with Aggregation-induced Emission High Thermal Stability,and Good Hole-transporting Property[J].J Mater Chem,2012,22:4527-4534.DOI:10.1039/C2JM14914A.
[27]Odabas S,Tekin E,Turksoy F,et al.Inexpensive and Valuable:a Series of New Luminogenic Molecules with The Tetraphenylethene Core Having Excellent Aggregation Induced Emission Properties[J].J Mater Chem C,2013,1:7081-7091.DOI:10.1039/C3TC31427H.
[28]Shi H,Gong Z,Xin D,et al.Synthesis,Aggregation-induced Emission and Electroluminescence Properties of a Novel Compound Containing Tetraphenylethene,Carbazole and Dimesitylboron Moieties[J].J Mater Chem C,2015,3:9095-9102.DOI:10.1039/C5TC01928A.
[29]Shi H,Wang S,Fang L,et al.Synthesis,Aggregation-induced Emission and Electroluminescence Properties of Two New Tetraphenylethene Derivatives[J].Tetrahedron Lett,2016,57:4428-4434.DOI:10.1016/j.tetlet.2016.08.072.
[30]Shi H,Li M,Xin D,et al.Two Novel Phenylethene-Carbazole Derivatives Containing Dimesitylboron Groups:Aggregation-induced Emission and Electroluminescence Properties[J].Dyes Pigm,2016,128:304-313.DOI:10.1016/j.dyepig.2016.01.028.
[31]Volyniuk D,Sutaite J,Tomkeviciene A,et al.Organic Light-emitting Diodes Exploiting Aggregation-induced Exciton and Exciplex Emissions[J].J Lumin,2017,192:534-540.DOI:10.1016/j.jlumin.2017.07.040.
[32]Tomkeviciene A,Sutaite J,Volyniuk D,et al.Aggregation-induced Emission Enhancement in Charge-transporting Derivatives of Carbazole and Tetra(tri)phenylethylene[J].Dyes Pigm,2017,140:363-374.DOI:10.1016/j.dyepig.2017.01.056.
[33]Cai Y,Shi C,Zhang H,et al.Sulfur-bridged Tetraphenylethylene AIEgens for Deep-blue Organic Light-emitting Diodes[J].J Mater Chem C,2018,6:6534-6542.DOI:10.1039/c8tc01509k.