3-boronic-N-(2-ethylhexyl)carbazole | 951226-01-0

• 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: 3-boronic-N-(2-ethylhexyl)carbazole
• 英文别名: 9-(2-ethylhexyl)-3-carbazoleboronic acid；9-(2-ethylhexyl)carbazolylboronic acid；N-(2-ethylhexyl)carbazole-3-boronic acid；[9-(2-Ethylhexyl)carbazol-3-yl]boronic acid
• CAS: 951226-01-0
• 化学式: C₂₀H₂₆BNO₂
• 分子量: 323.243
• InChiKey: SRARPTPHQDUZCU-UHFFFAOYSA-N

物化性质

• 沸点：
  474.0±51.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

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：

  3-boronic-N-(2-ethylhexyl)carbazole 、 2,5-双(4-溴苯基)-1,3,4-恶二唑 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以67%的产率得到2,5-bis(4-(9-(2-ethylhexyl)-9H-carbazol-3-yl)phenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Solution-processable highly efficient yellow- and red-emitting phosphorescent organic light emitting devices from a small molecule bipolar host and iridium complexes

  摘要：

  一种双极性传输化合物2,5-bis(4-(9-(2-乙基己基)-9H-氮杂芴-3-基)苯基)-1,3,4-噁二唑（CzOXD）合成并通过1H NMR、13C NMR、元素分析和质谱进行了全面表征。其热学、电化学、电子吸收和光致发光特性进行了研究。原子力显微镜图像表明，通过从CzOXD/铱复合物混合物的氯仿溶液中旋涂，可以获得光滑且均匀的薄膜。通过湿法工艺制造了高效的小分子有机发光器件。在器件结构为ITO/PEDOT:PSS/Ir复合物：CzOXD/BCP/Alq3/LiF/Al的条件下，获得了最大亮度为15232 cd m−2和电流效率为20 cd A−1的黄色发光OLED，以及在环境条件下获得了4896 cd m−2和4.6 cd A−1的红色发光OLED。

  DOI：

  10.1039/b806306k
• 作为产物：
  描述：

  9-(2-乙基己基)咔唑 在 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 3-boronic-N-(2-ethylhexyl)carbazole
  参考文献：
  名称：

  喹喔啉类有机染料及其合成方法

  摘要：

  本发明公开了一种喹喔啉类有机染料及其合成方法，引入喹喔啉单元(衍生物)作为辅助电子受体，以呋喃作为π‑桥，氰基丙烯酸作为电子受体，通过改变电子供体合成了一系列具有D‑A‑π‑A型喹喔啉类有机染料染料，其中在电子供体上引入烷基链，这有利于抑制染料分子的分子间聚集，增加染料的溶解性，且抑制TiO2电极中注入的电子与电解质中的之间的电子复合，从而改善DSSCs中的光伏性能，本发明制备的染料相比于传统的金属配位染料，展现出更好的摩尔消光系数、短路光电流密度和光电转换效率，从而极大的增强了太阳能电池的效率。

  公开号：

  CN112143252B

文献信息

• Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application
  作者：Gleb V. Baryshnikov、Pawel Gawrys、Khrystyna Ivaniuk、Bernhard Witulski、Richard J. Whitby、Ayham Al-Muhammad、Boris Minaev、Vladyslav Cherpak、Pavlo Stakhira、Dmytro Volyniuk、Gabriela Wiosna-Salyga、Beata Luszczynska、Algirdas Lazauskas、Sigitas Tamulevicius、Juozas V. Grazulevicius

  DOI：10.1039/c6tc01469k

  日期：——

  nine fused aromatic rings, including two pyrrole units, has been obtained in a straightforward and convergent synthesis. Computational chemistry and conformational analysis revealed that the semiconductor's molecule is not planar, the two carbazole moieties being helical twisted from the plane of the anthracene unit. Photophysical and electrochemical measurements showed that this angular fused heteroacene

  一种新的双咔唑并蒽由九个稠合的芳族环组成，包括两个吡咯单元，已通过简单且会聚的合成方法获得。计算化学和构象分析表明，半导体分子不是平面的，两个咔唑部分是从蒽单元的平面螺旋形扭曲的。光物理和电化学测量表明，尽管其扩展的π共轭分子框架，该角型稠合杂并苯具有低的HOMO能级和宽的带隙。基于其相对较低的HOMO水平，与其他相关的线性稠合并苯和杂并苯相比，该半导体具有较高的环境稳定性。双咔唑并蒽已被用作白色发光二极管（WOLED）中的发光层。提出白色OLED特征是由于来自活性半导体层的双重发光特性是基于小分子的分子发光和通过合适的固态聚集体而可能的离散的准分子发射。值得注意的是，这是在小分子杂并苯而不是低聚物或聚合物中观察到的这种行为的第一个报道实例。
• Photophysical characteristics and photosensitizing abilities of thieno[3,2-b]thiophene-Based photosensitizers for photovoltaic and photocatalytic applications
  作者：Po-Yu Ho、Yi Wang、Sze-Chun Yiu、Yan-Yi Kwok、Chi-Ho Siu、Cheuk-Lam Ho、Lawrence Tien Lin Lee、Tao Chen

  DOI：10.1016/j.jphotochem.2020.112979

  日期：2021.2

  2-b]thiophene π-linker comprising different alkyl side chains were synthesized and characterized. Their photophysical and electrochemical properties were studied and their corresponding performances as photosensitizers (PSs) in dye-sensitized solar cells (DSSCs) and photocatalytic hydrogen production systems were also investigated. A power conversion efficiency (PCE) of 5.25 % in DSSCs and a decent H2 turnover

  合成并表征了六种基于噻吩[3,2 - b ]噻吩π-连接基的施主-π-受体（D-π-A）有机染料。研究了它们的光物理和电化学性质，并研究了它们在染料敏化太阳能电池（DSSC）和光催化制氢系统中作为光敏剂（PSs）的相应性能。在镀铂的TiO 2制氢系统中，DSSC中的功率转换效率（PCE）为5.25％，H 2转化率（TON）为5170（48 h）。结果表明，烷基链工程是设计高级光敏剂的关键步骤之一。
• 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
• Solution-processable highly efficient yellow- and red-emitting phosphorescent organic light emitting devices from a small molecule bipolar host and iridium complexes
  作者：Youtian Tao、Qiang Wang、Chuluo Yang、Kai Zhang、Qi Wang、Taotao Zou、Jingui Qin、Dongge Ma

  DOI：10.1039/b806306k

  日期：——

  A bipolar transport compound, 2,5-bis(4-(9-(2-ethylhexyl)-9H-carbazol-3-yl)phenyl)-1,3,4-oxadiazole (CzOXD), incorporating both electron- and hole-transport functionalities, was synthesized and fully characterized by 1H NMR, 13C NMR, elemental analysis and mass spectrometry. Its thermal, electrochemical, electronic absorption and photoluminescent properties were studied. The atomic force microscopy images indicate that smooth and homogeneous films can be obtained by spin-coating from a chloroform solution of CzOXD/iridium complex blends. Highly efficient small-molecule-based organic light emitting devices were fabricated by a wet process. With the device structure of ITO/PEDOT:PSS/Ir complex : CzOXD/BCP/Alq3/LiF/Al, a maximum luminance of 15232 cd m−2 and current efficiency of 20 cd A−1 for a yellow-emitting OLED, and 4896 cd m−2, 4.6 cd A−1 for a red-emitting OLED were achieved under ambient conditions.

  一种双极性传输化合物2,5-bis(4-(9-(2-乙基己基)-9H-氮杂芴-3-基)苯基)-1,3,4-噁二唑（CzOXD）合成并通过1H NMR、13C NMR、元素分析和质谱进行了全面表征。其热学、电化学、电子吸收和光致发光特性进行了研究。原子力显微镜图像表明，通过从CzOXD/铱复合物混合物的氯仿溶液中旋涂，可以获得光滑且均匀的薄膜。通过湿法工艺制造了高效的小分子有机发光器件。在器件结构为ITO/PEDOT:PSS/Ir复合物：CzOXD/BCP/Alq3/LiF/Al的条件下，获得了最大亮度为15232 cd m−2和电流效率为20 cd A−1的黄色发光OLED，以及在环境条件下获得了4896 cd m−2和4.6 cd A−1的红色发光OLED。