N,N-bis(4-(3,6-di-tert-butylcarbazol-9-yl)phenyl)-4-(thiophen-2-yl)aniline | 1429922-06-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-bis(4-(3,6-di-tert-butylcarbazol-9-yl)phenyl)-4-(thiophen-2-yl)aniline
• 英文别名: N,N-bis[4-(3,6-di-tert-butylcarbazol-9-yl)phenyl]-4-(thiophen-2-yl)aniline；N,N-bis[4-(3,6-ditert-butylcarbazol-9-yl)phenyl]-4-thiophen-2-ylaniline
• CAS: 1429922-06-4
• 化学式: C₆₂H₆₃N₃S
• 分子量: 882.268
• InChiKey: BGTUABQUVJBOGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.3
• 重原子数：
  66
• 可旋转键数：
  10
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  41.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-bis(4-(3,6-di-tert-butylcarbazol-9-yl)phenyl)-4-(thiophen-2-yl)aniline 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91%的产率得到4,7-bis{5-(N,N-bis[4-(3,6-di-tert-butylcarbazol-N-yl)phenyl]aminophenyl)-thien-2-yl}-2,1,3-benzothiadiazole
  参考文献：
  名称：

  An efficient solution processed non-doped red emitter based on carbazole–triphenylamine end-capped di(thiophen-2-yl)benzothiadiazole for pure red organic light-emitting diodes

  摘要：

  新型咔唑-三苯胺端封二（噻吩-2-基）苯并噻二唑具有很高的热稳定性和电化学稳定性，作为溶液加工的OLED无掺杂空穴传输红色发射体的潜力巨大。 实现了具有CIE坐标和（0.66，0.33）的高亮度效率以及3.97 cd A∙1的纯红色器件。

  DOI：

  10.1039/c3cc41154k
• 作为产物：
  描述：

  2-噻吩硼酸 、 N,N-bis(4-(3,6-di-tert-butylcarbazol-9-yl)phenyl)-4-iodoaniline 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以72%的产率得到N,N-bis(4-(3,6-di-tert-butylcarbazol-9-yl)phenyl)-4-(thiophen-2-yl)aniline
  参考文献：
  名称：

  An efficient solution processed non-doped red emitter based on carbazole–triphenylamine end-capped di(thiophen-2-yl)benzothiadiazole for pure red organic light-emitting diodes

  摘要：

  新型咔唑-三苯胺端封二（噻吩-2-基）苯并噻二唑具有很高的热稳定性和电化学稳定性，作为溶液加工的OLED无掺杂空穴传输红色发射体的潜力巨大。 实现了具有CIE坐标和（0.66，0.33）的高亮度效率以及3.97 cd A∙1的纯红色器件。

  DOI：

  10.1039/c3cc41154k

文献信息

• Synthesis and Characterization of 2D-D-π-A-Type Organic Dyes Bearing Bis(3,6-di-<i>tert</i>-butylcarbazol-9-ylphenyl)aniline as Donor Moiety for Dye-Sensitized Solar Cells
  作者：Tanika Khanasa、Nittaya Jantasing、Somphob Morada、Nararak Leesakul、Ruangchai Tarsang、Supawadee Namuangruk、Tinnagon Kaewin、Siriporn Jungsuttiwong、Taweesak Sudyoadsuk、Vinich Promarak

  DOI：10.1002/ejoc.201201479

  日期：2013.5

  2D-D-π-A-type organic dyes, namely CCTTnA (n = 1–3), bearing bis(3,6-di-tert-butylcarbazol-9-ylphenyl)aniline as an electron-donor moiety (2D-D), oligothiophene segments with a number of thiophene units from one to three units as π-conjugated spacers (π), and cyanoacrylic acid as the electron acceptor (A) were synthesized and characterized as dye sensitizers for dye-sensitized solar cells (DSSCs). These

  一系列新型 2D-D-π-A 型有机染料，即 CCTTnA（n = 1-3），带有双（3,6-二-叔丁基咔唑-9-基苯基）苯胺作为电子供体部分(2D-D)，合成了具有 1 到 3 个噻吩单元作为 π 共轭间隔基 (π) 和氰基丙烯酸作为电子受体 (A) 的低聚噻吩链段，并将其表征为染料敏化太阳能的染料敏化剂细胞（DSSC）。这些化合物表现出高的热稳定性和电化学稳定性。对这些染料的详细研究表明，外围咔唑供体 (2D) 对溶液中染料和吸附在 TiO2 膜上的染料的红移吸收光谱以及入射单色光子到电流转换效率的加宽都有有益影响（IPCE）DSSC 的光谱，从而提高能量转换效率 (η)。在这些染料中，CCTT3A 显示出最好的光伏性能，最大入射单色光子到电流转换效率 (IPCE) 值为 80%，短路光电流密度 (Jsc) 为 9.98 mA cm-2，开路0.70 V 的电压 (Voc) 和 0.67
• Bis(carbazol-9-ylphenyl)aniline End-Capped Oligoarylenes as Solution-Processed Nondoped Emitters for Full-Emission Color Tuning Organic Light-Emitting Diodes
  作者：Tanika Khanasa、Narid Prachumrak、Rattanawaree Rattanawan、Siriporn Jungsuttiwong、Tinnagon Keawin、Taweesak Sudyoadsuk、Thawatchai Tuntulani、Vinich Promarak

  DOI：10.1021/jo4008332

  日期：2013.7.5

  A series of bis(3,6-di-tert-butylcarbazol-9-ylphenyl)aniline end-capped oligoarylenes, BCPA-Ars, are synthesized by double palladium-catalyzed cross-coupling, reactions. By using this bis(carbazol-9-yl)triphenylamine moiety as an end cap, we are able to reduce the crystallization and retain the high emission ability of these planar fluorescent oligoarylene cores in the solid state, as well as improve the amorphous stability and solubility of the materials. The results of optical and electrochemical studies show that their HOMOs, LUMOs, and energy gaps can be easily modified or fine-tuned by either varying the degree of pi-conjugation or using electron affinities of the aryl cores which include fluorene, oligothiophenes, 2,1,3-benzothiadiazole, 4,7-diphenyl-4-yl-2,1,3-benzothiadiazole, and 4,7-dithien-2-yl-2,1,3-benzothiadiazole. As a result, their emission spectra measured in solution and thin films can cover the full UV-vis spectrum (426-644 nm). Remarkably, solution-processed nondoped BCPA-Ars-based OLEDs could show moderate to excellent device performance with emission colors spanning the whole visible spectrum (deep blue to red). Particularly, the RGB (red, green, blue) OLEDs exhibit good color purity close to the pure RGB colors. This report offers a practical approach for both decorating the highly efficient but planar fluorophores and tuning their emission colors to be suitable for applications in nondoped and solution-processable full-color emission OLEDs.