9-ethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) carbazole | 1311405-88-5

• 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-ethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) carbazole
• 英文别名: 9-Ethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole
• CAS: 1311405-88-5
• 化学式: C₂₀H₂₄BNO₂
• 分子量: 321.227
• InChiKey: WJLFWWYYMIHTJC-UHFFFAOYSA-N

物化性质

• 沸点：
  426.8±27.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-ethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) carbazole 在 iron(III) chloride 、 四(三苯基膦)钯 、 吡啶盐酸盐 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 7.0h， 生成 10-ethyl-10H-phenanthro[9,10-b]carbazol-3-ol
  参考文献：
  名称：

  PHENANTHROCARBAZOLE COMPOUND, AND ORGANIC ELECTROLUMINESCENT DEVICE USING SAME

  摘要：

  本发明涉及一种用于有机电致发光器件的材料，包括具有特定结构的苯并咔唑基化合物，以及包括该化合物的有机电致发光器件。更具体地说，苯并咔唑基化合物被应用为磷光和荧光有机电致发光器件的材料，从而提供具有改善发光效率、亮度、热稳定性、驱动电压、寿命等特性的有机发光器件。

  公开号：

  US20130048975A1
• 作为产物：
  描述：

  2-溴咔唑 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 7.0h， 生成 9-ethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) carbazole
  参考文献：
  名称：

  超分子聚合物中自适应芳香族阳离子π驱动的尺寸多晶型用于芳香族/环状脂肪族化合物的光催化氧化和分离

  摘要：

  分子构件的精确组装对于设计超分子组装体 (SA) 的多态性至关重要。我们开发了一种自适应芳香族阳离子-π结合基序来控制单体的自组装方向性，以促进二维（2D）和三维（3D）结晶超分子结构的创建。这些多态SA将在各个领域得到应用。

  DOI：

  10.1002/anie.202402760

文献信息

• Air stable electron-transporting and ambipolar bay substituted perylene bisimides
  作者：Renji R. Reghu、Hari Krishna Bisoyi、Juozas V. Grazulevicius、Padmesh Anjukandi、Valentas Gaidelis、Vygintas Jankauskas

  DOI：10.1039/c1jm11091h

  日期：——

  Four new perylene bisimides containing carbazolyl and triphenylamino electron-donor groups in the bay region have been designed, synthesized and characterized. The materials possess high thermal stability and form uniform films. They display a wide absorption window extending to the near infrared region of the spectrum and demonstrate efficient photoinduced intramolecular electron transfer. Ionization potential values of these perylene bisimide derivatives measured by photoelectron spectroscopy range from 5.8 eV to 6 eV. Charge-transporting properties were investigated by the xerographic time of flight (XTOF) technique. Complementary ambipolar charge-transport was observed in differently linked carbazolyl substituted perylene bisimides while the triphenylamino substituted material exhibited competent electron drift mobility (>10−3 cm2 V−1 cm−1) under ambient conditions. Density functional theory (DFT) calculations were performed for carbazolyl bay substituted perylene bisimides in order to understand the complementary ambipolar charge transport as well as the difference in the optical properties.

  设计、合成并表征了四种新型的含有卡巴唑和三苯胺电子供体基团的贝尔林双酰亚胺，主要集中在其边缘区域。这些材料具有高热稳定性，并形成均匀的薄膜。它们在光谱中展现了延伸至近红外区域的宽吸收窗口，并显示出有效的光诱导分子内电子转移。这些贝尔林双酰亚胺衍生物的电离势值通过光电子光谱测量，范围在5.8 eV到6 eV之间。通过静电复印时间飞行（XTOF）技术研究了其电荷传输特性。在不同连接方式的卡巴唑取代的贝尔林双酰亚胺中观察到互补的双极电荷传输，而三苯胺取代的材料在环境条件下展现出良好的电子漂移迁移率（>10−3 cm² V−1 s−1）。为理解互补的双极电荷传输及其光学性质差异，进行了卡巴唑边替代贝尔林双酰亚胺的密度泛函理论（DFT）计算。
• Structure–properties relationship of carbazole and fluorene hybrid trimers: experimental and theoretical approaches
  作者：Ausra Tomkeviciene、Juozas V. Grazulevicius、Dmytro Volyniuk、Vygintas Jankauskas、Gjergji Sini

  DOI：10.1039/c4cp00302k

  日期：——

  Synthesis and properties of fluorene and carbazole derivatives having three electrophores per molecule with different architectures are reported. The synthesized compounds possess high thermal stabilities with 5% weight loss temperatures exceeding 350 °C. They form glasses with glass transition temperatures ranging from 60 to 68 °C. Cyclovoltammetric experiments revealed the high electrochemical stability of the fluorene trimer. In contrast, 2- and 2,7-fluorenyl substituted carbazole derivatives show irreversible oxidation in the CV experiments. The electron photoemission spectra of the films of the synthesized compounds revealed ionization potentials of 5.65–5.89 eV. Hole drift mobilities in the amorphous layers of the synthesized compounds reach 10−2 cm2 V−1 s−1 at high electric fields, as established by a xerographic time-of-flight technique. DFT calculations show that HOMO and LUMO orbitals of the compounds are very similar in energy and shape. The similar hole mobilities observed for the three compounds are discussed in the frame of the Marcus theory. An important influence of the alkyl groups on the ionization potentials and on the hole mobilities was also observed and its origin is discussed.

  本文报道了具有不同结构、每个分子有三个电荷的芴和咔唑衍生物的合成和性质。合成的化合物具有很高的热稳定性，5%重量损失温度超过350°C。它们形成的玻璃的玻璃化转变温度在60到68°C之间。循环伏安实验表明芴三聚体具有很高的电化学稳定性。相比之下，2-和2,7-芴基取代的咔唑衍生物在CV实验中表现出不可逆的氧化。合成化合物的薄膜的电子光发射光谱显示电离电位为5.65-5.89eV。根据静电复印飞行时间技术，合成化合物的非晶层中的空穴漂移迁移率在强电场下达到10-2 cm2 V-1 s-1。DFT计算表明化合物的HOMO和LUMO轨道在能量和形状上非常相似。在Marcus理论的框架下讨论了三种化合物中观察到的相似空穴迁移率。还观察到烷基对电离电位和空穴迁移率的重要影响，并讨论了其起源。
• Phenanthrocarbazole compound, and organic electroluminescent device using same
  申请人：Hong Jin-Seok

  公开号：US09017829B2

  公开（公告）日：2015-04-28

  The present invention relates to a material for an organic electroluminescent device, including a phenanthrocarbazole-based compound having a specific structure, and an organic electroluminescent device including the same. More specifically, the phenanthrocarbazole-based compound is applied as a material for a phosphorescent and fluorescent organic electroluminescent device, thereby providing an organic light emitting device with improved light emitting efficiency, luminance, thermal stability, driving voltage, lifetime and the like.

  本发明涉及一种用于有机电致发光器件的材料，包括一种具有特定结构的菲咯咔唑基化合物和包括其的有机电致发光器件。更具体地，该菲咯咔唑基化合物被应用为磷光和荧光有机电致发光器件的材料，从而提供了一种具有改进的发光效率、亮度、热稳定性、驱动电压、寿命等特性的有机发光器件。
• 一类强D-A型有机近红外二区发光材料的合成及其应用
  申请人：桂林理工大学

  公开号：CN117865950A

  公开（公告）日：2024-04-12

  本发明属于生物医学材料领域，提供了一类具有AIE性质的近红外二区发光材料的制备及其应用，其结构为：#imgabs0#，其中Ar为具有AIE性质的基团如三苯胺和咔唑衍生物，X为氢元素，氟元素和氯元素等，本发明的近红外发光材料具有AIE性质，其合成简单，且近红外发光效率高、吸收和发射光谱可调、光稳定好，能够克服生物组织的自吸收和自发荧光的干扰等优点。
• Systematic Structure–Property Investigations on a Series of Alternating Carbazole–Thiophene Oligomers
  作者：Shin-ichiro Kato、Satoru Shimizu、Atsushi Kobayashi、Toshitada Yoshihara、Seiji Tobita、Yosuke Nakamura

  DOI：10.1021/jo402416f

  日期：2014.1.17

  A series of alternating carbazole-thiophene oligomers, namely 2,7-linked carbazole-thiophene oligomers 1, 3, 5, 7, and 9 and 3,6-linked ones 2, 4, 6, 8, and 10, in which the molecular length was systematically elongated, were synthesized by Suzuki-Miyaura coupling reactions. The effects of the conjugation connectivity between the carbazole and thiophene moieties and the molecular length on the electronic, photophysical, and electrochemical properties of 1-10 were comprehensively investigated. In the present oligomer architectures, the connection with thiophene at the 2,7-positions of carbazole ensures pi-conjugation to a high extent and high fluorescence quantum yields, while that at the 3,6-positions enhances the donor ability. The increase in the molecular length of the 2,7-linked oligomers effectively extends pi-conjugation. The relationship between structural variations and photophysical properties was examined by fluorescence lifetime measurements in detail. The X-ray crystal structure of 6 was also disclosed.