methyl (1R,4aS,10aR)-1,4a-dimethyl-7-(N-(4-phenylphenyl)anilino)-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate | 1450984-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: methyl (1R,4aS,10aR)-1,4a-dimethyl-7-(N-(4-phenylphenyl)anilino)-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• CAS: 1450984-69-6
• 化学式: C₃₆H₃₇NO₂
• 分子量: 515.695
• InChiKey: OVKKUKWOMOXGNY-ICMREOOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 13-amino-deisopropyldehydroabietate 在 三叔丁基膦 、 palladium diacetate 、 sodium t-butanolate 作用下， 以 邻二甲苯 为溶剂， 生成 methyl (1R,4aS,10aR)-1,4a-dimethyl-7-(N-(4-phenylphenyl)anilino)-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
  参考文献：
  名称：

  Synthesis and properties of new luminescent hole transporting materials of triarylamine with dehydroabietic acid methyl ester moieties

  摘要：

  A series of triarylamines based on dehydroabietic acid methyl ester moieties (6a-h) were synthesized for possible application as hole transporting materials for organic electroluminescent devices. The target compounds were characterized by elemental analysis, FT-IR, NMR, and mass spectrometry. Their optical, electrochemical, and thermal properties were investigated using UV-vis, PL spectroscopy, cyclic voltammetry (CV), thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC), respectively. CV measurements show that the compounds present suitable HOMO values (in a range of -4.63 to -5.11 eV) for hole injection, which is confirmed by theoretical calculations. All compounds were thermally stable. Organic light-emitting diode devices having 6f, 6g, and 6h as a hole transporting layer showed better performance of maximum brightness, turn-on voltage, and maximum luminous efficiency than a comparable device NPB. These compounds could be excellent candidates for applications in OLED devices. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.071

文献信息

• 一类基于脱氢枞酸芳环的化合物及其制备方法
  申请人：中国林业科学研究院林产化学工业研究所

  公开号：CN108658801A

  公开（公告）日：2018-10-16

  本发明提供了一类基于脱氢枞酸芳环的化合物及其制备方法。以脱氢枞酸为原料经过酯化、硝化、还原、C‑N偶联反应得到式1所示化合物，再以式1所示化合物为原料与NBS反应得到式2所示化合物，最后以式2所示化合物与芳环硼酸反应得到式3所示化合物。本发明反应条件温和，操作简单。
• Three series π-extended fluorescent compounds based on dehydroabietic acid triarylamine moiety: Syhthesis, photophysical properties and hole transporting properties
  作者：Guanni Tan、Jie Song、Xinwen Zhang、Yanan Gao、Shibin Shang、Zhanqian Song、Hong Gao

  DOI：10.1016/j.dyepig.2020.108551

  日期：2020.10

  Fluorescent compounds based on a dehydroabietic acid skeleton with favorable photophysical properties show promise for use as the hole-transporting layer in organic light-emitting diodes (OLEDs). In this work, we report the synthesis of three series of compounds (15 in total), series 1 (1a–1e), series 2 (2a–2e), and series 3 (3a–3e), by linking polycyclic aromatic hydrocarbons (PAHs) to dehydroabietic

  基于具有良好光物理性质的脱氢松香酸骨架的荧光化合物显示出有望用作有机发光二极管（OLED）中的空穴传输层。在这项工作中，我们报告了三个系列化合物（总共15个），系列1（1a - 1e），系列2（2a - 2e）和系列3（3a - 3e）的合成。），方法是通过CC偶联反应将多环芳烃（PAH）与基于脱氢松香酸的三芳胺部分连接。这三个系列的化合物表现出紫外线吸收，荧光发射，电化学和热学性质，以及最高的分子轨道能级和能隙，使其适合用作空穴传输材料。具有1a，2a或3d作为空穴传输层的OLED在最大亮度，开启电压，最大外部量子效率，最大发光效率和功率效率方面表现出比基于常规器件的同类设备更好的性能空穴传输材料。特别是带有1a的设备具有最高的性能，最大亮度为21445 cd / m 2，低开启电压为2.8 V，最大外部量子效率为1.62％，最大亮度效率为4.9 cd / A，最大功率效率为3.7 lm