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第 36 卷第 4 期                             精   细   化   工                                  Vol.36, No.4
             201 9 年 4 月                             FINE CHEMICALS                                 Apr.    2019


              有机电化学与工业
                 三芳胺-均苯三甲酰胺衍生物的自组装及光电性能



                                                         1
                                                                      1*
                                            1
                                   历成龙 ,蒋艺斐 ,张   宝 ,冯亚青                             1,2
                       (1.  天津大学  化工学院,天津    300350;2.  天津化学化工协同创新中心,天津    300072)

                 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。
                 关键词:三芳胺;均苯三甲酰胺;自组装;空穴传输材料;钙钛矿太阳能电池;有机电化学与工业
                 中图分类号:TQ630      文献标识码:A      文章编号:1003-5214 (2019) 04-0730-07


                                Self-assembly and Photoelectric Properties of an

                            Triarylamine-1,3,5-benzenetricarboxamide Derivative

                                                                                        1,2
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                                                                        1*
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                                LI Cheng-long , JIANG Yi-fei , ZHANG Bao , FENG Ya-qing
                 〔1. School of  Chemical Engineering and Technology, Tianjin  University, Tianjin  300350, China;  2. The  National
                 Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China〕
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                                                                               5
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                 Abstract:  A  triarylamine-1,3,5-benzenetricarboxamide  derivative,  N ,N ,N -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.
                 Key words: triarylamine; 1,3,5-benzenetricarboxamide; self-assembly; hole transport material; perovskite
                 solar cell; electro-organic chemistry and industry
                 Foundation  items:  National  Natural  Science  Foundation  of  China  (21761132007);  Tianjin  Science  and
                 Technology Innovation Platform Program (14TXGCCX00017)


                                                                                              [1]
                 有机功能分子在光电转换、催化、传感器等领                          的相互作用及其形成的聚集态结构 。超分子聚合
            域具有非常大的应用前景。其在器件中的应用性能                             物是溶液态或凝聚态的单体通过具有明确方向性和
            不仅取决于有机分子的结构,而且取决于分子之间                             可逆性的非共价键作用力(氢键、离子键、π-π堆


                 收稿日期:2018-08-22;  定用日期:2018-12-24; DOI: 10.13550/j.jxhg.20180617
                 基金项目:国家自然科学基金(21761132007);天津市科技创新平台计划(14TXGCCX00017)
                 作者简介:历成龙(1993—),男,硕士生,E-mail:lclgoogoo@163.com。联系人:张   宝(1976—),男,副教授,E-mail:baozhang@tju.edu.cn。
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