三芳胺-均苯三甲酰胺衍生物的自组装及光电性能
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摘要
以对碘苯酚和溴代正十二烷为原料,合成了一种三芳胺-均苯三甲酰胺基衍生物N,N?,N?-三{3-[(4-{双[4-(十二烷氧基)苯基]氨基}苯基)氨基]丙基}-1,3,5-苯三甲酰胺(H1),以超分子组装的方法实现了三芳胺功能单元的长程有序排列。紫外-可见吸收光谱及荧光光谱研究表明,H1在弱极性溶剂正庚烷中有较明显的自组装特性;分别用光学显微镜和SEM观察了H1的自组装形貌;通过量子化学计算和电化学性质测试考察了H1的空穴传输性能,计算结果和实验测得的HOMO能级(?5.14 eV)、LUMO能级(?1.80 eV)均与钙钛矿的HOMO能级(?5.43 eV)和LUMO能级(?3.93 eV)匹配,同时测得H1的热分解温度为445℃。研究表明,H1可以作为空穴传输材料在有机电化学与工业中应用于钙钛矿太阳能电池。
A triarylamine-1,3,5-benzenetricarboxamide derivative, N1,N3,N5-tris[3-(4-{bis[4-(dodecyloxy)phenyl]amino}phenylamino)propyl]benzene-1,3,5-tricarboxamide(H1) was synthesized by using 4-iodophenol and 1-bromododecane as raw materials. And ordered long range arrangement of triarylamine functional units was achieved by using a supramolecular assembly method. UV-vis absorption and fluorescence spectra showed that H1 had self-assembly characteristics in the weak polar solvent n-heptane. The self-assembly morphology of H1 was observed by optical microscope and SEM, respectively. Further,quantum chemical calculations and electrochemical measurements were performed. The calculated results and measured HOMO level(?5.14 eV) and LUMO level(?1.80 eV) were matched with the HOMO level(?5.43 eV) and LUMO level(?3.93 eV) of perovskite. The thermal decomposition temperature of H1 was found to be 445 ℃. Thus, H1 could be applied as a hole transport material in the perovskite solar cell of electro-organic chemistry and industry.
A triarylamine-1,3,5-benzenetricarboxamide derivative, N1,N3,N5-tris[3-(4-{bis[4-(dodecyloxy)phenyl]amino}phenylamino)propyl]benzene-1,3,5-tricarboxamide(H1) was synthesized by using 4-iodophenol and 1-bromododecane as raw materials. And ordered long range arrangement of triarylamine functional units was achieved by using a supramolecular assembly method. UV-vis absorption and fluorescence spectra showed that H1 had self-assembly characteristics in the weak polar solvent n-heptane. The self-assembly morphology of H1 was observed by optical microscope and SEM, respectively. Further,quantum chemical calculations and electrochemical measurements were performed. The calculated results and measured HOMO level(?5.14 eV) and LUMO level(?1.80 eV) were matched with the HOMO level(?5.43 eV) and LUMO level(?3.93 eV) of perovskite. The thermal decomposition temperature of H1 was found to be 445 ℃. Thus, H1 could be applied as a hole transport material in the perovskite solar cell of electro-organic chemistry and industry.
引文
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[3]Xu Jiangfei(徐江飞),Zhang Xi(张希).Study on supramolecular polymers in china:An overview and outlook[J].Acta Polymerica Sinica(高分子学报),2017,(1),37-48.
[4]Kong Xiangfei(孔翔飞),Yao Wei(姚威),Dai Shengping(戴胜平),et al.Progress of intermolecular self-assembled discotic liquid crystal materials[J].Fine Chemicals(精细化工),2018,35(3):361-371.
[5]Yan X,Wang F,Zheng B,et al.Stimuli-responsive supramolecular polymeric materials[J].Chemical Society Reviews,2012,41(18):6042-6065.
[6]Jain A,George S J.New directions in supramolecular electronics[J].Materials Today,2015,18(4):206-214.
[7]Li Xianggao(李祥高),Wu Anshu(吴安树),He Lili(何莉莉),et al.Synthesis and property of 4-(4?,4′-diphenyl-1?,3?-butadienyl)-N,N-bis(4?-methylphenyl)aniline[J].Fine Chemicals(精细化工),2005,22(8):572-574.
[8]Liang M,Chen J.Arylamine organic dyes for dye-sensitized solar cells[J].Chemical Society Reviews,2013,42(8):3453-3488.
[9]Meng Xiangfang(孟祥芳),Li Xianggao(李祥高),Wang Shirong(王世荣).Multifunctional polymeric electroluminescent materials[J].Fine Chemicals(精细化工),2002,19(12):703-706.
[10]Ge Mengyuan(葛梦媛),Zhao Xin(赵鑫),Yan Qiufang(严秋钫),et al.Synthesis and spectral and electrochemical properties of novel triphenylamine derivatives[J].Fine Chemicals(精细化工),2012,29(3):231-249.
[11]Bordeau G,Lartia R,Metge G,et al.Trinaphthylamines as robust organic materials for two-photon-induced fluorescence[J].Journal of the American Chemical Society,2008,130(50):16836-16837.
[12]Moulin E,Niess F,Maaloum M,et al.The hierarchical self-assembly of charge nanocarriers:A highly cooperative process promoted by visible light[J].Angewandte Chemie,2010,49(39):6974-6978.
[13]Mouliné,Busseron E,Domoto Y,et al.Self-assembly of benzenetris[bis(p-benzyloxy)triphenylamine]carboxamide[J].Comptes RendusChimie,2016,19(1/2):117-122.
[14]Huang X L,Zou J H,Liu J Z,et al.A high Tg small-molecule arylamine derivative as a doped hole-injection/transport material for stable organic light-emitting diodes[J].Organic Electronics,2018,58:139-144.
[15]Xing L B,Yang B,Wang X J,et al.Reversible sol-to-gel transformation of uracil gelators:Specific colorimetric and fluorimetric sensor for fluoride ions[J].Langmuir,2013,29(9):2843-2848.
[16]Meng Lingzhi(孟令芝),Gong Shuling(龚淑玲),He Yongbing(何永炳).Organic spectral analysis[M].2nd ed.Wuhan:Wuhan University Press(武汉:武汉大学出版社),2003:115-117.
[17]Van H R,van Buul A M,Castriciano M A,et al.Supramolecular porphyrin polymers in solution and at the solid-liquid interface.[J].Nano Letters,2008,8(1):253-259.
[18]Reddy N M,Pan T Y,Rajan Y C,et al.Porphyrin sensitizers withπ-extended pull units for dye-sensitized solar cells[J].Physical Chemistry Chemical Physics,2013,15(21):8409-8415.
[19]Wu Qichao(吴启超),Qiu Hailing(丘海玲),Xie Bowen(谢博文),et al.Synthesis and photovoltaic application research of two asymmetric perylene diimide small molecules[J].Fine Chemicals(精细化工),2017,34(10):1180-1184.
[20]Wang Haiying(王海营).Study on design,synthesis and characterization of fluorescent molecules based on arylamine[D].Suzhou:Suzhou University(苏州:苏州大学),2010.
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