1-[N-(4-methylphenyl)-N-phenylamino]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene | 908120-28-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-[N-(4-methylphenyl)-N-phenylamino]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
• 英文别名: N-tolyl-N-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline；N-(4-methylphenyl)-N-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine；N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Ph)-N-Ph-4-methyl-aniline；N-(4-methylphenyl)-N-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)Benzenamine；N-(4-methylphenyl)-N-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS: 908120-28-5
• 化学式: C₂₅H₂₈BNO₂
• 分子量: 385.314
• InChiKey: JPZHLLGPGKEKAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  1-[N-(4-methylphenyl)-N-phenylamino]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene 在 四(三苯基膦)钯 、 potassium carbonate 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 生成
  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 2,6-二甲基吡啶 、 aluminum (III) chloride 、 三氯化硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 1-[N-(4-methylphenyl)-N-phenylamino]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
  参考文献：
  名称：

  Simple inexpensive boron electrophiles for direct arene borylation

  摘要：

  使用由廉价试剂（特别是胺、三氯化硼（BCl3）和三氯化铝（AlCl3））生成的亲电子试剂，可以促进亲电子直接硼化反应，并扩大芳烃底物的适用范围。

  DOI：

  10.1039/c1cc14226g

文献信息

• [EN] PROCESS FOR THE BORYLATION OF ARENES AND HETEROARYLS<br/>[FR] PROCÉDÉ DE BORYLATION D'ARÈNES ET D'HÉTÉROARYLES
  申请人：UNIV MANCHESTER

  公开号：WO2012025760A1

  公开（公告）日：2012-03-01

  This invention relates to a novel process for the borylation of arenes and heteroaryls. The present invention also provides novel borenium cations, which act as electrophiles for electrophilic substitution on the arene or heteroaryl ring, as well as to methodology for the preparation of these cations.

  这项发明涉及一种新型芳烃和杂环芳烃硼化的过程。本发明还提供了新型硼离子阳，它们作为芳烃或杂环芳烃环上亲电取代的亲电试剂，以及用于制备这些阳离子的方法学。
• JP6081210
  申请人：——

  公开号：——

  公开（公告）日：——
• JP6091240
  申请人：——

  公开号：——

  公开（公告）日：——
• Chemically Doped and Cross-linked Hole-Transporting Materials as an Efficient Anode Buffer Layer for Polymer Solar Cells
  作者：Ying Sun、Shang-Chieh Chien、Hin-Lap Yip、Yong Zhang、Kung-Shih Chen、David F. Zeigler、Fang-Chung Chen、Baoping Lin、Alex K.-Y. Jen

  DOI：10.1021/cm2024235

  日期：2011.11.22

  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.
• Simple inexpensive boron electrophiles for direct arene borylation
  作者：Alessandro Del Grosso、Matthew D. Helm、Sophia A. Solomon、Dolores Caras-Quintero、Michael J. Ingleson

  DOI：10.1039/c1cc14226g

  日期：——

  Electrophilic direct borylation is facilitated, and arene substrate scope enhanced, by using electrophiles derived from inexpensive reagents; specifically an amine, BCl3 and AlCl3.

  使用由廉价试剂（特别是胺、三氯化硼（BCl3）和三氯化铝（AlCl3））生成的亲电子试剂，可以促进亲电子直接硼化反应，并扩大芳烃底物的适用范围。