9-(2-ethylhexyl)carbazol-2-ylboronic acid | 951225-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(2-ethylhexyl)carbazol-2-ylboronic acid
• 英文别名: 2-boronic-N-(2-ethylhexyl)carbazole；[9-(2-Ethylhexyl)carbazol-2-yl]boronic acid
• CAS: 951225-99-3
• 化学式: C₂₀H₂₆BNO₂
• 分子量: 323.243
• InChiKey: DUMJTAJLKLNHTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-(2-ethylhexyl)carbazol-2-ylboronic acid 在 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 49.0h， 生成 dichloro[10,13-bis(9-(2-ethylhexyl)carbazol-2-yl)dipyrido[3,2-a:2',3'-c]phenazine-N⁴,N⁵]platinum(II)
  参考文献：
  名称：

  Novel 10,13-disubstituted dipyrido[3,2-a:2′,3′-c]phenazines and their platinum(II) complexes: highly luminescent ICT-type fluorophores based on D–A–D structures

  摘要：

  DOI：

  10.1016/j.tetlet.2014.07.069
• 作为产物：
  描述：

  2-溴-9-(2-乙基己基)-9H-咔唑 在 正丁基锂 、 硼酸三异丙酯 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 24.0h， 以67%的产率得到9-(2-ethylhexyl)carbazol-2-ylboronic acid
  参考文献：
  名称：

  Tuning the Intramolecular Charge Transfer Emission from Deep Blue to Green in Ambipolar Systems Based on Dibenzothiophene S,S-Dioxide by Manipulation of Conjugation and Strength of the Electron Donor Units

  摘要：

  The efficient synthesis and photophysical propel ties of a series of ambipolar donor acceptor donor Systems is described where the acceptor is dibenzothrophene S,S-dioxide and the donor is fluorene, carbazole or arylamine The systems exhibit intramolecular charge transfer (ICT) states (available ICT character strengths)}editing to fluorescence emission ranging from deep blue to green with model ate to high photoluminescence quantum yields The emission properties can be effectively tuned by systematically changing die position of substitution on both donor and acceptor units (which affects the extent of conjugation) and the redox potentials of the donor units The results are supported by cyclic voltammetric data and TD-DFT calculations

  DOI：

  10.1021/jo100898a

文献信息

• Improving the performance of phosphorescent polymer light-emitting diodes using morphology-stable carbazole-based iridium complexes
  作者：Kai Zhang、Zhao Chen、Chuluo Yang、Xiaowei Zhang、Youtian Tao、Lian Duan、Liang Chen、Linna Zhu、Jingui Qin、Yong Cao

  DOI：10.1039/b705342h

  日期：——

  A series of morphology-stable carbazole-based iridium(III) complexes with green to red emission have been prepared and characterized by elemental analysis, nuclear magnetic resonance, and mass spectroscopy. Their thermal, electrochemical, electronic absorption, and photoluminescent properties have been studied. Highly efficient polymer light-emitting devices by using these complexes as dopant emitters, both non-conjugated polymer (PVK) and conjugated polymer, polyhedral oligomeric silsesquioxane-terminated poly(9,9-dioctylfluorene) [PFO(poss)], as the host materials, have been achieved. With the device structure of ITO/PEDOT/(PFO(poss) + 30% PBD)–2 wt.% 1/Ba/Al, a maximum external quantum efficiency of 6.4% and a maximum luminous efficiency of 6.00 cd A−1 with red emission at 608 nm were obtained. With the device configuration of ITO/PEDOT/(PFO(poss) + 30% PBD)–4 wt.% 4/Ba/Al, a maximum external quantum efficiency of 9.9% and a maximum luminous efficiency of 22.4 cd A−1 with yellow–green emission at 544 nm were realized. The increased morphology stability of 1 and 2 imparted by the N-decyl long chains at the N atom of carbazole results in significantly better device performance than their short chain analogues 1a and 2a under identical device configurations.

  我们制备了一系列形态稳定的咔唑基铱（III）配合物，这些配合物具有绿色至红色发射，并通过元素分析、核磁共振和质谱对其进行了表征。研究了它们的热学、电化学、电子吸收和光致发光特性。利用这些复合物作为掺杂发射体，以非共轭聚合物（PVK）和共轭聚合物--多面体低聚硅倍半氧烷端聚（9,9-二辛基芴）[PFO(poss)]为宿主材料，实现了高效的聚合物发光器件。采用 ITO/PEDOT/(PFO(poss) + 30% PBD)-2 wt.% 1/Ba/Al 的器件结构，获得了 6.4% 的最大外部量子效率和 6.00 cd A-1 的最大发光效率，并在 608 nm 处发出红色光。在 ITO/PEDOT/(PFO(poss) + 30% PBD)-4 wt.% 4/Ba/Al 的器件配置下，最大外部量子效率为 9.9%，最大发光效率为 22.4 cd A-1，在 544 纳米波长处发出黄绿色光。咔唑 N 原子上的 N-癸基长链提高了 1 和 2 的形态稳定性，因此在相同的器件配置下，其器件性能明显优于短链类似物 1a 和 2a。
• Tuning the Intramolecular Charge Transfer Emission from Deep Blue to Green in Ambipolar Systems Based on Dibenzothiophene <i>S</i>,<i>S</i>-Dioxide by Manipulation of Conjugation and Strength of the Electron Donor Units
  作者：Kathryn C. Moss、Konstantinos N. Bourdakos、Vandana Bhalla、Kiran T. Kamtekar、Martin R. Bryce、Mark A. Fox、Helen L. Vaughan、Fernando B. Dias、Andrew P. Monkman

  DOI：10.1021/jo100898a

  日期：2010.10.15

  The efficient synthesis and photophysical propel ties of a series of ambipolar donor acceptor donor Systems is described where the acceptor is dibenzothrophene S,S-dioxide and the donor is fluorene, carbazole or arylamine The systems exhibit intramolecular charge transfer (ICT) states (available ICT character strengths)}editing to fluorescence emission ranging from deep blue to green with model ate to high photoluminescence quantum yields The emission properties can be effectively tuned by systematically changing die position of substitution on both donor and acceptor units (which affects the extent of conjugation) and the redox potentials of the donor units The results are supported by cyclic voltammetric data and TD-DFT calculations
• Novel 10,13-disubstituted dipyrido[3,2-a:2′,3′-c]phenazines and their platinum(II) complexes: highly luminescent ICT-type fluorophores based on D–A–D structures
  作者：Tatsuya Shigehiro、Shigeyuki Yagi、Takeshi Maeda、Hiroyuki Nakazumi、Hideki Fujiwara、Yoshiaki Sakurai

  DOI：10.1016/j.tetlet.2014.07.069

  日期：2014.9