4-(二苯基氨基)苯基硼酸二甲酯 | 1019056-21-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-(二苯基氨基)苯基硼酸二甲酯
• 英文名称: dimethyl 4-(diphenylamino)phenylboronate
• 英文别名: 4-dimethoxyboranyl-N,N-diphenylaniline
• CAS: 1019056-21-3
• 化学式: C₂₀H₂₀BNO₂
• 分子量: 317.195
• InChiKey: SZNYLJBYFLHNHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  438.2±28.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(二苯基氨基)苯基硼酸二甲酯 在 盐酸 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 甲苯 为溶剂， 反应 20.0h， 生成 1-(3',5'-dibromophenyl)-4-diphenylaminobenzene
  参考文献：
  名称：

  Synthesis of Triphenylamine-Modified Arylates and Ketones via Suzuki Coupling Reactions

  摘要：

  [image omitted] A series of triphenylamine-mdified arylates and ketones were synthesized via Pd-catalyzed Suzuki coupling reaction of triphenylamine boronic acid with aryl bromide. The triphenylamine boronic acid was synthesized by iodization of 4-bromoaniline, Ullmann reaction of 1-bromo-4-iodobenzene with diphenylamine, and boronic acidification of 4-bromotriphenylamine.

  DOI：

  10.1080/00397911003706982
• 作为产物：
  描述：

  对溴碘苯 在 正丁基锂 、 copper(l) chloride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 邻二甲苯 、 甲苯 为溶剂， 反应 48.0h， 生成 4-(二苯基氨基)苯基硼酸二甲酯
  参考文献：
  名称：

  Synthesis of Triphenylamine-Modified Arylates and Ketones via Suzuki Coupling Reactions

  摘要：

  [image omitted] A series of triphenylamine-mdified arylates and ketones were synthesized via Pd-catalyzed Suzuki coupling reaction of triphenylamine boronic acid with aryl bromide. The triphenylamine boronic acid was synthesized by iodization of 4-bromoaniline, Ullmann reaction of 1-bromo-4-iodobenzene with diphenylamine, and boronic acidification of 4-bromotriphenylamine.

  DOI：

  10.1080/00397911003706982

文献信息

• Efficient and stable dye-sensitized solar cells based on phenothiazine sensitizers with thiophene units
  作者：Wenjun Wu、Jiabao Yang、Jianli Hua、Jin Tang、Lei Zhang、Yitao Long、He Tian

  DOI：10.1039/b918282a

  日期：——

  Three new phenothiazine organic dyes containing thiophene, 3-(5-(3-(4-(bis(4-methoxy phenyl)amino)phenyl)-10-octyl-10H-phenothiazin-7-yl)thiophen-2-yl)-2-cyanoacrylic acid (P1), 3-(5-(3-(4-(diphenylamino)phenyl)-10-octyl-10H-phenothiazin-7-yl)thiophen-2-yl)-2-cyanoacrylic acid (P2) and 2-cyano-3-(5-(10-octyl-3-(4-(2,2-diphenylvinyl)phenyl)-10H-phenothiazin-7-yl)thiophen-2-yl) acrylic acid (P3) were designed and synthesized as sensitizers for application in dye-sensitized solar cells (DSSCs). For these dyes, the phenothiazine derivative moiety and the cyanoacetic acid take the roles of electron donor and electron acceptor, respectively. The absorption spectra, electrochemical and photovoltaic properties of P1–P3 and the cell long-term stability were extensively investigated. It was found that HOMO and LUMO energy level tuning can be conveniently accomplished by alternating the donor moiety. The DSSCs based on dye P2 showed the best photovoltaic performance: a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 84.9%, a short-circuit photocurrent density (Jsc) of 10.84 mA cm−2, an open-circuit photovoltage (Voc) of 592 mV, and a fill factor (ff) of 0.69, corresponding to an overall conversion efficiency of 4.41% under standard global AM 1.5 solar light conditions. These results demonstrated that the DSSCs based on phenothiazine dyes could achieve both high performance and good stability.

  设计并合成了三种含有噻吩的新的苯噻嗪有机染料：3-(5-(3-(4-(二(4-甲氧基苯基)氨基)苯基)-10-辛基-10H-苯噻嗪-7-基)噻吩-2-基)-2-氰基丙烯酸 (P1)、3-(5-(3-(4-(二苯基氨基)苯基)-10-辛基-10H-苯噻嗪-7-基)噻吩-2-基)-2-氰基丙烯酸 (P2) 和2-氰基-3-(5-(10-辛基-3-(4-(2,2-二苯乙烯)苯基)-10H-苯噻嗪-7-基)噻吩-2-基)丙烯酸 (P3)，作为染料敏化太阳能电池（DSSCs）的敏化剂。在这些染料中，苯噻嗪衍生物部分和氰基丙烯酸分别充当电子供体和电子受体。对P1–P3的吸收光谱、电化学和光电性能以及电池的长期稳定性进行了广泛研究。研究发现，通过交替供体部分可以方便地调节HOMO和LUMO能级。基于染料P2的DSSCs表现出最佳的光电性能：在标准全球AM 1.5太阳光条件下，最大单色入射光子电流转换效率（IPCE）为84.9%，短路光电流密度（Jsc）为10.84 mA/cm²，开路光电压（Voc）为592 mV，填充因子（ff）为0.69，整体转换效率为4.41%。这些结果表明，基于苯噻嗪染料的DSSCs能够实现高性能和良好的稳定性。
• Violet-blue- or pure-blue-emitting triphenylamine derivatives: synthesis and properties
  作者：Zhi-Ping Wu、Gui-Jun Liu、Cai-Cai Zhu、Zhi-Mei Li、Xi-Cun Gao、Qian-Yong Cao

  DOI：10.1139/cjc-2012-0473

  日期：2013.11

  We report the synthesis and optoelectronic properties of a series of nine triphenylamine derivatives. They were synthesized by Suzuki cross-coupling reactions and characterized by elemental analysis, nuclear magnetic resonance, ultraviolet visible absorption spectra, fluorescence spectra, and cyclic voltammetry. All compounds exhibit reversibly electrochemical behavior. In solid state, compounds 5 and 9 emit near violet blue and compounds 1, 2, 4, 6, 7, and 8 emit deep blue or pure blue and compound 3 emits green. Of all of these compounds, compounds 1, 3, 4, and 8 exhibit high fluorescence quantum yields (44%–68%) with the best coplanarity. Compared with them, compounds 5 and 9 have the lowest fluorescence quantum yields due to the least coplanarity. With the similarity in structure with those reported in literature, these compounds can be potentially useful for blue-emitting, host, and up-converting materials.

  我们报告了一系列九种三苯胺衍生物的合成和光电特性。它们通过铃木偶联反应合成，并通过元素分析、核磁共振、紫外可见吸收光谱、荧光光谱和循环伏安法进行表征。所有化合物均表现出可逆的电化学行为。在固态中，化合物5和9发出近紫蓝色光，化合物1、2、4、6、7和8发出深蓝色或纯蓝色光，化合物3发出绿色光。在所有这些化合物中，化合物1、3、4和8表现出高荧光量子产率（44%–68%），并具有最佳的共面性。与它们相比，化合物5和9由于共面性最差，荧光量子产率最低。与文献中报道的结构相似，这些化合物有望用于蓝光发射、宿主和上转换材料。
• New D—D—π-A triphenylamine–coumarin sensitizers for dye-sensitized solar cells
  作者：Ji He、Yang Liu、Jianrong Gao、Liang Han

  DOI：10.1039/c6pp00410e

  日期：2017.7

  Three D–D–π-A triphenylamine–coumarin sensitizers were designed and synthesized with a triphenylamine and coumarin double donor and a cyanoacrylic acid acceptor. Thiophene, bithiophene and phenylthiophene were used as π-bridges, respectively, and the effects of different π-bridges on the photophysical properties and photovoltaic performance were investigated. With the incorporation of an additional

  设计并使用三苯胺和香豆素双供体和氰基丙烯酸受体合成了三种D-D-π-A三苯胺-香豆素敏化剂。分别以噻吩，联噻吩和苯基噻吩为π桥，研究了不同π桥对光物理性质和光电性能的影响。通过并入一个额外的噻吩单元，联噻吩π桥有助于更好的光吸收，因此具有更好的J SC与噻吩的π桥相比。尽管具有苯基噻吩π桥的染料比噻吩π桥的染料具有较差的吸收光谱，但它的光电转换效率为4.99％，并表现出三种敏化剂的最佳光电性能，这归因于其有效的光子对光子效应。电流转换效率，慢的电荷复合速率和良好的电子注入效率。
• Bithiazole-bridged dyes for dye-sensitized solar cells with high open circuit voltage performance
  作者：Jinxiang He、Wenjun Wu、Jianli Hua、Yihua Jiang、Sanyin Qu、Jing Li、Yitao Long、He Tian

  DOI：10.1039/c0jm03811c

  日期：——

  Five new metal-free organic dyes (T1–T5) containing bithiazole moieties were synthesized and used for dye-sensitized solar cells (DSSCs). Their absorption spectra, electrochemical and photovoltaic properties were fully characterized. Electrochemical measurement data indicate that the tuning of the HOMO and LUMO energy levels can be conveniently accomplished by alternating the donor moiety. All of these dyes performed as sensitizers for the DSSC test, and the photovoltaic performance data of these bithiazole-bridged dyes showed higher open circuit voltages (745–810 mV). Among the five dyes, T1 showed the best photovoltaic performance: a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 83.8%, a short-circuit photocurrent density (Jsc) of 11.78 mA cm−2, an open-circuit photovoltage (Voc) of 810 mV, and a fill factor (ff) of 0.60, corresponding to an overall conversion efficiency of 5.73% under standard global AM 1.5 solar light condition, which reached 93% with respect to that of an N719-based device fabricated under similar conditions. The result shows that the metal-free dyes based on bithiazole π-conjugation are promising candidates for improvement of the performance of DSSCs.

  合成了五种含有双噻唑分子的新型无金属有机染料（T1-T5），并将其用于染料敏化太阳能电池（DSSC）。对它们的吸收光谱、电化学和光伏特性进行了全面表征。电化学测量数据表明，通过交替使用供体分子，可以方便地调整 HOMO 和 LUMO 能级。所有这些染料在 DSSC 测试中都发挥了敏化剂的作用，而且这些双噻唑桥联染料的光电性能数据显示出较高的开路电压（745-810 mV）。在这五种染料中，T1 的光伏性能最好：最大单色入射光子到电流的转换效率（IPCE）为 83.8%，短路光电流密度（Jsc）为 11.78 mA cm-2，开路光电电压（Voc）为 810 mV，填充因子（ff）为 0.与在类似条件下制造的基于 N719 的器件相比，该器件的转换效率达到 93%。结果表明，基于双噻唑π共轭的无金属染料是提高 DSSC 性能的理想候选材料。
• Novel organic dyes with anchoring group of quinoxaline-2, 3-diol and the application in dye-sensitized solar cells
  作者：Lei Wang、Xichuan Yang、Xiuna Wang、Licheng Sun

  DOI：10.1016/j.dyepig.2014.09.019

  日期：2015.2

  Two organic quinoxaline dyes (WQ-1 and WQ-2) with a structure of quinoxaline-2, 3-diol as the electron withdrawing and anchoring group were synthesized and applied in the dye-sensitized solar cells. Fourier transform infrared spectroscopy and two other reference dyes (WQ-R1 and WQ-R2) without the hydroxyl groups were introduced to ascertain the adsorption properties of the dye series. The effect of the new electron acceptor and anchoring group on the performance of solar cells was investigated systematically. Under the standard light illumination (100 mW m(-2)), WQ-2 got an efficiency of 2.25%, with a short circuit photocurrent density of 5.51 mA cm(-2), an open circuit voltage of 0.612 V and a fill factor of 66.74%. (C) 2014 Elsevier Ltd. All rights reserved.