2,2,2′,2′-四(苯并咪唑-2-基)-1,4-二乙烯基苯的合成及其光电性能
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摘要
以邻苯二胺、丙二酸及对苯二甲醛为原料,通过Knoevenagel反应合成了一种多苯并咪唑有机光电材料2,2,2′,2′-四(1H-苯并咪唑-2-基)-1,4-二乙烯基苯。采用包括元素分析、FTIR和1 H NMR分析在内的方法对其结构进行了表征,并测试研究了产物的光物理性能、电化学特性和热稳定性。结果表明:该化合物的最大紫外吸收谱在398nm附近的近紫外光区。其溶液荧光为λem≈500nm的蓝绿色光,固体薄膜荧光为λem=554nm的绿色光,且具有明显的聚集诱导发光增强(AIEE)效应。通过CV测得其Eg=3.10eV,IP=5.57eV,EA=2.47eV,表明该化合物是一种潜在空穴传输材料。测得其热分解温度接近500℃,具有良好的热稳定性。采用密度泛函(DFT)理论计算其主要光电性能参数,与实验结果相符,量化计算证明该分子具有显著的非共平面性的π共轭体系以及分子内电荷转移特性。
A novel photoelectric material 2,2,2′,2′-tetra(benzimidazole-2-yl)-1,4-divinylbenzene was synthesized through Knoevenagel reaction.Its structure was characterized by various methods including elemental analysis,etc.Measurements and tests for photophysical properties,electrochemical properties and thermal stability were carried out.The results showed that the compound has two UV absorption peaks locating at 280 nm and 398 nm and a blue-green fluorescenceλem,max=500 nm excited by 365 nm in DMF.A significant AIEE effect of the compound was found with different DMA/H2O ratio inmixed solvent.It has a green fluorescence(λem,max=554 nm)in solid with a 54 nm red shift compared to the solution fluorescence.Eg=3.10 eV,Ip=5.57 eV and EA=2.47 eV calculated from CV test indicated the compound may be a potential hole transporting material.TG-DTA analysis showed that the compound with a thermal decomposition temperature(500℃)possess good thermal stability.The optimized ground-state geometry,HOMO and LUMO distributions of the compound were obtained by DFT.The results from DFT calculation is consistent with that of experiments and revealed that the compound has a largely nonplanarπelectron conjugated system and notable intramolecular charge transferring performance.
A novel photoelectric material 2,2,2′,2′-tetra(benzimidazole-2-yl)-1,4-divinylbenzene was synthesized through Knoevenagel reaction.Its structure was characterized by various methods including elemental analysis,etc.Measurements and tests for photophysical properties,electrochemical properties and thermal stability were carried out.The results showed that the compound has two UV absorption peaks locating at 280 nm and 398 nm and a blue-green fluorescenceλem,max=500 nm excited by 365 nm in DMF.A significant AIEE effect of the compound was found with different DMA/H2O ratio inmixed solvent.It has a green fluorescence(λem,max=554 nm)in solid with a 54 nm red shift compared to the solution fluorescence.Eg=3.10 eV,Ip=5.57 eV and EA=2.47 eV calculated from CV test indicated the compound may be a potential hole transporting material.TG-DTA analysis showed that the compound with a thermal decomposition temperature(500℃)possess good thermal stability.The optimized ground-state geometry,HOMO and LUMO distributions of the compound were obtained by DFT.The results from DFT calculation is consistent with that of experiments and revealed that the compound has a largely nonplanarπelectron conjugated system and notable intramolecular charge transferring performance.
引文
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[2]Pan B,Wang B,Wang Y,et al.A simple carbazole-N-benzimidazole bipolar host material for highly efficient blue and single layer white phosphorescent organic light-emitting diodes[J].Journal of Materials Chemistry C,2014,2(14):2466~2469.
[3]Bodedla G B,Thomas K R J,Kumar S,et al.Phenothiazinebased bipolar green-emitters containing benzimidazole units:synthesis,photophysical and electroluminescence properties[J].RSC Advnces,2015,5(106):87416~87428.
[4]Esteves C I C,Raposo M M M,Costa S P G.Synthesis and evaluation of benzothiazolyl and benzimidazolyl asparagines as amino acid based selective fluorimetric chemosensors for Cu2+[J].Tetrahedron,2010,66(38):7479~7486.
[5]Batista R M F,Costa S P G,Raposo M M M.Naphthylimidazo-anthraquinones as novel colorimetric and fluorimetric chemosensors for ion sensing[J].Journal of Photochemistry and Photobiology A,2013,259(3):33~40.
[6]Molina P,Tarraga A,Oton F.Imidazole derivatives:Acomprehensive survey of their recognition properties[J].Organic&Biomolecular Chemistry,2012,10(9):1711~1724.
[7]Yilmaz U,Sireci N,Deniz S,et al.Synthesis and microwaveassisted catalytic activity of novel bis-benzimidazole salts bearing furfuryl and thenylmoieties in Heck and Suzuki cross-coupling reactions[J].Applied Organometallic Chemistry,2010,24(5):414~420.
[8]Zhao J,Hu Y,Dong Y,et al.Novel bluish green benzimidazole-based iridium(III)complexes for highly efficient phosphorescent organic light-emitting diodes[J].New Journal of Chemistry,2017,41(5):1973~1979.
[9]Huang J-J,Hung Y-H,Ting P-L,et al.Orthogonally substituted benzimidazole-carbazole benzene as universal hosts for phosphorescent organic light-emitting diodes[J].Organic Letters,2016,18(4):672~675.
[10]Nomura M,Shibasaki Y,Ueda M,et al.New amorphous electron-transporting materials based on tris-benzimidazoles for all wet-process OLED devices[J].Synthetic Metals,2005,151(3):261~268.
[11]Muangpaisal R,Hung W-I,Lin J-T,et al.Binaphthalene bridged bipolar transporting materials for blue electroluminescence:toward high EL efficiency via molecular tuning[J].Tetrahedron,2014,70(18):2992~2998.
[12]Luo Z,Zhu H,Song G,et al.Synthesis and photophysical properties of a series of thermally stable terphenyl-bridged bisbenzimidazoles[J].Dyes and Pigments,2011,88(3):274~279.
[13]Takizawa S Y,Montes V A,Anzenbacher J P.Phenylbenzimidazole-based new bipolar host materials for efficient phosphorescent organic light-emitting diodes[J].Chemistry of Materials,2009,21(12):2452~2458.
[14]Jiang W,Tang J,Ban X,et al.Ideal bipolar host materials with bis-benzimidazole unit for highly efficient solution-processed green electrophosphorescent devices[J].Organic Letters,2014,16(20):5346~5349.
[15]钱永,王建军,张蓉,等.1,1-二(苯并咪唑-2-基)-2-(N-乙基咔唑-3-基)乙烯的合成及其性能研究[J].发光学报,2014,35(6):96~101.
[16]王建军,钱永,龚菁,等.1,1-二(苯并咪唑-2-基)-2-(喹喔啉-2-基)乙烯的合成及其性能[J].合成化学,2015,23(2):281~284.
[17]Sonawane Y A,Rajule R N,Shankarling G S.Synthesis of novel diphenylamine-based fluorescent styryl colorants and study of their thermal,photophysical,and electrochemical properties[J].Monatshefte fur Chemie,2010,141(10):1145~1151.
[18]祁争健,韦斌,王雪梅,等.基于3,4-二烷氧基噻吩的D-A-D型有机共轭分子的合成及其光学和电化学性能[J].物理化学学报,2010,26(12):3310~3316.
[19]Wang M,Zhang G,Zhang D,et al.Fluorescent bio/chemosensors based on silole and tetraphenylethene luminogens with aggregation-induced emission feature[J].Journal of Materials Chemistry,2010,20(1):1858~1867.
[20]Zhao Z,Jacky W Y L,Tang B.Aggregation-induced emission of tetraarylethene luminogens[J].Current Organic Chemistry,2010,14(18):2109~2132.
[21]Ozdemir N,Dayan O,Yavasoglu M T,et al.Synthesis and characterization of 2,2’-(pyridine-2,6-diyl)bis(1H-benzo[d]imidazol-3-ium)2,4,6-trimethylbenzenesulfonate chloride by experimental and theoretical methods[J].Spectrochim Acta A,2014,131:145~152.
[22]Jedrzejewska B,Krawczyk P,Pietrzak M,et al.Styryl dye possessing donor-π-acceptor structure,synthesis,spectroscopic and computational studies[J].Dyes and Pigments,2013,99(3):673~685.
[23]赵跃智,蔡敏敏,钱妍,等.聚集诱导发光体系:化合物种类、发光机制及其应用[J].化学进展,2013,25(2):296~321.
[24]邵晶,赵鑫,林朝阳,等.双极性菲并咪唑有机发光材料的合成与性能[J].材料科学与工程学报,2014,32(1):64~69.
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