4-溴-N-苯基-N-对甲苯苯胺 | 183798-74-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-溴-N-苯基-N-对甲苯苯胺
• 中文别名: N-(4-溴苯基)-N-(4-甲基苯基)苯胺
• 英文名称: N-(4-bromo-phenyl)-N-(4-methylphenyl)aniline
• 英文别名: 4-bromo-N-phenyl-N-(4'-methylphenyl)aniline；(4-bromophenyl)(phenyl)p-tolylamine；4-Bromo-N-(4-methylphenyl)-N-phenylaniline；N-(4-bromophenyl)-4-methyl-N-phenylaniline
• CAS: 183798-74-5
• 化学式: C₁₉H₁₆BrN
• 分子量: 338.247
• InChiKey: YMEBIIALDLSINE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-溴-N-苯基-N-对甲苯苯胺 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 生成 4,4'-([2,2'-bithiophene]-5,5'-diyl)bis(N-phenyl-N-(p-tolyl)aniline)
  参考文献：
  名称：

  Chemically Doped and Cross-linked Hole-Transporting Materials as an Efficient Anode Buffer Layer for Polymer Solar Cells

  摘要：

  A series of cross-linkable hole-transporting materials (X-HTMs) consisting of indacenodithiophene, bithiophene, and thiophene units bookended by two triarylamine groups have been designed and synthesized to investigate their suitability as new anode buffer layer for bulk heterojunction polymer solar cells (PSCs). These X-HTMs can be thermally cross-linked at temperature between 150 and 180 C to form robust, solvent-resistant films for subsequent spin-coating of another upper layer. Energy levels of these cross-linked materials were measured by cyclic voltammetry, and the data suggest that these X-HTMs have desirable hole-collecting and electron-blocking abilities to function as an anode buffer layer for PSCs. In addition, by incorporating thiophene or fused ring units into the X-HTM backbone, it effectively improved the hole-carrier motilities. To further improve the conductivity and optical transparency for PSCs, the X-HTM films were p-doped with nitrosonium hexafluoroantimonate (NOSbF6). The doped X-HTM layers showed remarkably enhanced hole-current densities compared to neutral X-HTM under the same electric field bias. The properties of the doped X-HTM film as anode buffer layer has been investigated in PSCs. The resulting devices showed similar performance compared to those made using conducting polymer, poly(3,4-ethylene- dioxylenethiophene):poly(styrenesulfonate) (PEDOT:PSS), as the anode buffer layer. Moreover, a novel bilayer HTM structure consisting of a doped and a neutral layer was employed to exploit the feasibility of combining high conductivity from the doped X-HTM and good electron-blocking ability from the neutral X-HTM together. Interestingly, PSC devices based on this bilayer structure showed enhanced V-oc, J(sc), and FF compared to the devices with only a single-layer doped X-HTM. These results indicate that such X-HTMs are promising alternative materials to PEDOT:PSS as an anode buffer layer for polymer solar cells.

  DOI：

  10.1021/cm2024235
• 作为产物：
  描述：

  4-甲基三苯胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以90%的产率得到4-溴-N-苯基-N-对甲苯苯胺
  参考文献：
  名称：

  Chemically Doped and Cross-linked Hole-Transporting Materials as an Efficient Anode Buffer Layer for Polymer Solar Cells

  摘要：

  A series of cross-linkable hole-transporting materials (X-HTMs) consisting of indacenodithiophene, bithiophene, and thiophene units bookended by two triarylamine groups have been designed and synthesized to investigate their suitability as new anode buffer layer for bulk heterojunction polymer solar cells (PSCs). These X-HTMs can be thermally cross-linked at temperature between 150 and 180 C to form robust, solvent-resistant films for subsequent spin-coating of another upper layer. Energy levels of these cross-linked materials were measured by cyclic voltammetry, and the data suggest that these X-HTMs have desirable hole-collecting and electron-blocking abilities to function as an anode buffer layer for PSCs. In addition, by incorporating thiophene or fused ring units into the X-HTM backbone, it effectively improved the hole-carrier motilities. To further improve the conductivity and optical transparency for PSCs, the X-HTM films were p-doped with nitrosonium hexafluoroantimonate (NOSbF6). The doped X-HTM layers showed remarkably enhanced hole-current densities compared to neutral X-HTM under the same electric field bias. The properties of the doped X-HTM film as anode buffer layer has been investigated in PSCs. The resulting devices showed similar performance compared to those made using conducting polymer, poly(3,4-ethylene- dioxylenethiophene):poly(styrenesulfonate) (PEDOT:PSS), as the anode buffer layer. Moreover, a novel bilayer HTM structure consisting of a doped and a neutral layer was employed to exploit the feasibility of combining high conductivity from the doped X-HTM and good electron-blocking ability from the neutral X-HTM together. Interestingly, PSC devices based on this bilayer structure showed enhanced V-oc, J(sc), and FF compared to the devices with only a single-layer doped X-HTM. These results indicate that such X-HTMs are promising alternative materials to PEDOT:PSS as an anode buffer layer for polymer solar cells.

  DOI：

  10.1021/cm2024235

文献信息

• Biocompatible Nanoparticles with Aggregation Induced Emission Characteristics as Fluorescent Bioprobes and Methods of Using the Same for In Vitro and In Vivo Imaging
  申请人：Tang Benzhong

  公开号：US20140328764A1

  公开（公告）日：2014-11-06

  The development of fluorescent bioprobes comprising organic fluorescent compounds that exhibit aggregation induced emission (AIE) properties, methods of producing the same, and their practical applications for in vitro and in vivo bioimaging.

  有机荧光化合物构成的发光生物探针的发展，其具有聚集诱导发射（AIE）特性，生产方法以及它们在体外和体内生物成像方面的实际应用。
• 由三苯胺构建的主体大环和多侧枝三苯胺空穴 传输材料
  申请人：孔庆刚

  公开号：CN104030995B

  公开（公告）日：2016-07-06

  本发明提供一种由三苯胺构建的主体大环上取代有多个三苯胺侧枝空穴传输材料。通过将2-溴芴酮构建到含有能相互反应的功能团三苯胺单体中，进一步将三分子这样的单体环化，再通过简单的化学反应，在大环的侧面至少再构建三个三苯胺侧枝结构，形成一类含多个三苯胺构建的主体大环和侧枝型富电子空穴传输材料。该富电子式a、式b、式c大环型三芳胺化合物具有近似三维球形结构。本发明所设计合成的富电子大环型三芳胺化合物具有较高的玻璃化温度，能形成稳定的、均匀的无定型薄膜，无420纳米以上波长的荧光发射，可作为空穴传输材料用于光电转换器件中。
• 3D Monodisperse Oligofluorenes with Non-Conjugated Triphenylamine-Based Cores: Synthesis and Optoelectronic Properties
  作者：Xiaomo Zhang、Yiwu Quan、Zhe Cui、Qingmin Chen、Jianfu Ding、Jianping Lu

  DOI：10.1002/ejoc.200901140

  日期：2010.4

  Two 3D monodisperse oligofluorenes with non-conjugated triphenylamine-based cores have been synthesized by Friedel-Crafts copolycondensation reaction. The oligomers, PF 3 -TPA and PF 3 -TPA 3 , consist of three fluorene pentamer arms that are connected non-conjugately through a triphenylamine (TPA) and 1,3,5-tris(triphenylamino)benzene core (TPA 3 ), respectively, at the 9-position of the central fluorene

  通过 Friedel-Crafts 共缩聚反应合成了两种具有非共轭三苯胺基核的 3D 单分散低聚芴。低聚物PF 3 -TPA 和PF 3 -TPA 3 由三个芴五聚体臂组成，它们通过三苯胺（TPA）和1,3,5-三（三苯氨基）苯核（TPA 3 ）非共轭连接，分别位于五芴臂中心芴的 9 位。核的共面结构和五芴臂中心的连接产生了低聚物的 3D 结构。这种特殊的结构有效地延缓了五芴臂的结晶趋势，并使材料完全无定形的形态结构。两种低聚物都在薄膜中发出高效率的深蓝色荧光（Φ pl-film = PF 3 -TPA 3 的 67% 和 PF 3 -TPA 的 86%）。在核中引入三苯胺单元促进了空穴注入能力，同时没有明显削弱低聚物的电子注入能力。制造多层器件 ITO/PEDOT-PSS/PF 3 -TPA 3 和 PF 3 -TPA/TPBI/LiF/Al 以研究两种低聚物的电致发光 (EL) 特性。两种低聚物都显示出
• [EN] NOVEL COMPOUNDS, DERIVATIVES THEREOF AND THEIR USE IN HETEROJUNCTION DEVICES<br/>[FR] NOUVEAUX COMPOSÉS, LEURS DÉRIVÉS ET LEUR UTILISATION AU SEIN DE DISPOSITIFS À HÉTÉROJONCTION
  申请人：UNIV MELBOURNE

  公开号：WO2010060160A1

  公开（公告）日：2010-06-03

  The invention relates to novel polyaromatic and polyheteroaromatic compounds and derivatives thereof. The compounds display high solubility in organic solvents. A further aspect of the invention relates to the use of the novel compounds in the fabrication of organic film based heterojunction devices. In one form the devices display high conversion efficiencies in solar cell applications.

  该发明涉及新型多芳香和多杂芳化合物及其衍生物。这些化合物在有机溶剂中显示出很高的溶解度。该发明的另一个方面涉及将这些新型化合物用于制造基于有机薄膜的异质结器件。在某种形式中，这些器件在太阳能电池应用中显示出很高的转换效率。
• [EN] HETEROCYCLIC COMPOUNDS AND THEIR USE IN ELECTRO-OPTICAL OR OPTO-ELECTRONIC DEVICES<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEUR UTILISATION DANS DES DISPOSITIFS ÉLECTRO-OPTIQUES OU OPTO-ÉLECTRONIQUES
  申请人：POWER OLEDS LTD

  公开号：WO2017013420A1

  公开（公告）日：2017-01-26

  Compounds exhibiting high hole mobility and/or high glass transition temperatures together with favourable HOMO, LUMO and triplet levels are provided which are 2-(4'-Diphenylamino)phenyl-8-(1'-thianthrenyl)- dibenzothiophene and 4-(1-Thianthrenyl)-bis(triphenylamine). The compounds may be used for hole transport layers e.g. in OLED devices.

  提供了表现出高空穴迁移率和/或高玻璃转变温度以及有利的HOMO、LUMO和三重态能级的化合物，其中包括2-(4'-二苯胺基)苯基-8-(1'-噻芴基)-二苯并噻吩和4-(1-噻芴基)-双(三苯胺)。这些化合物可以用于有机发光二极管（OLED）设备中的空穴传输层。