3,6-bis(trimethylsilylethynyl)-9-butylcarbazole | 426266-11-7

• 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: 3,6-bis(trimethylsilylethynyl)-9-butylcarbazole
• 英文别名: 2-[9-Butyl-6-(2-trimethylsilylethynyl)carbazol-3-yl]ethynyl-trimethylsilane
• CAS: 426266-11-7
• 化学式: C₂₆H₃₃NSi₂
• 分子量: 415.726
• InChiKey: XHEUYZFJBQHSTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,6-bis(trimethylsilylethynyl)-9-butylcarbazole 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以95%的产率得到3,6-diethynyl-9-butylcarbazole
  参考文献：
  名称：

  咔唑连接的卟啉镊子的合成与表征

  摘要：

  本文报道了3,6-二取代咔唑镊子的合成，光谱表征，双光子吸收和电化学性质。在二乙炔基-咔唑间隔基和5-溴-三芳基卟啉之间的Sonogashira偶联反应过程中，分离了Glaser偶合产生的二聚体，并将该原始化合物的性质与3,6-二取代咔唑双卟啉镊子进行了比较。本文报道的二元组在920 nm处具有最大的两个光子吸收，且两个光子的吸收截面在1200 GM范围内。尽管在Soret区有很强的线性吸收和适度的荧光量子产率，但它们均导致达到30 000 M -1  cm -1的高亮度 。

  DOI：

  10.1002/chem.201501619
• 作为产物：
  描述：

  N-正丁基咔唑 在 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 54.0h， 生成 3,6-bis(trimethylsilylethynyl)-9-butylcarbazole
  参考文献：
  名称：

  咔唑连接的卟啉镊子的合成与表征

  摘要：

  本文报道了3,6-二取代咔唑镊子的合成，光谱表征，双光子吸收和电化学性质。在二乙炔基-咔唑间隔基和5-溴-三芳基卟啉之间的Sonogashira偶联反应过程中，分离了Glaser偶合产生的二聚体，并将该原始化合物的性质与3,6-二取代咔唑双卟啉镊子进行了比较。本文报道的二元组在920 nm处具有最大的两个光子吸收，且两个光子的吸收截面在1200 GM范围内。尽管在Soret区有很强的线性吸收和适度的荧光量子产率，但它们均导致达到30 000 M -1  cm -1的高亮度 。

  DOI：

  10.1002/chem.201501619

文献信息

• Novel Diethynylcarbazole Macrocycles:  Synthesis and Optoelectronic Properties
  作者：Tianyue Zhao、Zhanxiang Liu、Yabin Song、Wei Xu、Deqing Zhang、Daoben Zhu

  DOI：10.1021/jo0611869

  日期：2006.9.1

  Diethynylcarbazole macrocycles 1b and 2b have been synthesized by oxidative coupling of appropriate precursors. In particular, macrocycle 2b was prepared by bimolecular Pd-catalyzed oxidative coupling in 35% isolated yield. The spectroscopic properties of these macrocycles and their precursors were measured in detail. The films of these macrocycles by the dipping method and the Langmuir-Blodgett technique were fabricated to study their photoinduced charge-transfer properties. A rapid and steady cathodic photocurrent of these films was produced in a three-electrode cell when irradiated with white light. A possible mechanism of the photoinduced electron-transfer pathway was suggested.
• Synthesis of a Nanocar with an Angled Chassis. Toward Circling Movement
  作者：Takashi Sasaki、Andrew J. Osgood、Lawrence B. Alemany、Kevin F. Kelly、James M. Tour

  DOI：10.1021/ol702642r

  日期：2008.1.1

  Nanocars with an angled chassis have been synthesized and imaged using scanning tunneling microscopy. These angled chassis nanocars were designed to further our understanding of the directional control and surface-rolling capabilities of this class of nanomachines. The alkylated carbazole inner core might enable the molecular scaffold to produce circular rolling motions of the nanovehicles on surfaces.
• Synthesis and Characterization of Carbazole-Linked Porphyrin Tweezers
  作者：Yi Chang、Clément Michelin、Léo Bucher、Nicolas Desbois、Claude P. Gros、Sébastien Piant、Frédéric Bolze、Yuanyuan Fang、Xiaoqin Jiang、Karl M. Kadish

  DOI：10.1002/chem.201501619

  日期：2015.8.17

  Herein the synthesis, spectroscopic characterization, two‐photon absorption and electrochemical properties of 3,6‐disubstituted carbazole tweezers is reported. A dimer resulting from a Glaser homocoupling was isolated during a Sonogashira coupling reaction between a diethynyl‐carbazole spacer and a 5‐bromo‐triarylporphyrin and the properties of this original compound were compared with the 3,6‐disubstituted

  本文报道了3,6-二取代咔唑镊子的合成，光谱表征，双光子吸收和电化学性质。在二乙炔基-咔唑间隔基和5-溴-三芳基卟啉之间的Sonogashira偶联反应过程中，分离了Glaser偶合产生的二聚体，并将该原始化合物的性质与3,6-二取代咔唑双卟啉镊子进行了比较。本文报道的二元组在920 nm处具有最大的两个光子吸收，且两个光子的吸收截面在1200 GM范围内。尽管在Soret区有很强的线性吸收和适度的荧光量子产率，但它们均导致达到30 000 M -1  cm -1的高亮度 。
• Electroactive Dyes Based on 1,8‐Naphthalimide with Acetylene Linkers as Promising OLED Materials – the Relationship Between Structure and Photophysical Properties
  作者：Marek Matussek、Aneta Kurpanik‐Wójcik、Szymon Gogoc、Aleksandra Fijołek、Michał Filapek、Beata Naumczuk、Przemysław Data

  DOI：10.1002/chem.202302115

  日期：2023.11.2

  Four A‐π‐D‐π‐A type small organic molecules with 1,8‐naphthalimide motifs were successfully synthesised. The designed compounds are built of two 1,8‐naphthalimide units linked via ethynyl π‐linkages with selected functionalised donor motifs i. e. 2,2’‐bithiophene, fluorene, phenothiazine and carbazole derivative. The synthesis based on Sonogashira cross‐coupling allowed us to obtain the presented dyes with good yields. The resulting symmetrical small molecules’ optical, electrochemical and thermal properties were thoroughly investigated, and their potential applicability for the OLED devices was demonstrated. In addition, the relationship between molecular structure and properties was considered by employing experimental and theoretical studies. As a result of using various donor groups, it was possible to achieve efficient electroluminescence in the range from green (DEV4) to orange‐red light (DEV3) with a maximum luminance of 3 820 cd/m² for DEV4. Upon the insertion of an acetylene linker to the designed molecules, the free rotation of D and A fragments, and hence the effective π‐electron communication within the entire molecule, is possible, which was confirmed by DFT studies. The obtained dyes are characterised by high thermal stability, reversible oxidation‐reduction process, satisfactory optoelectronic properties and good solubility in organic solvents, which is advisable for the application in small molecular organic light‐emitting diodes (SM‐OLEDs) technology.

  摘要 成功合成了四种具有 1,8-萘二甲酰亚胺基团的 A-π-D-π-A 型有机小分子。所设计的化合物由两个 1,8-萘二甲酰亚胺单元通过乙炔基 π 链接与选定的功能化供体基团（即 2,2'-联噻吩荧光基团）连接而成。2,2'-联噻吩、芴、吩噻嗪和咔唑衍生物。基于 Sonogashira 交叉偶联的合成方法使我们能够以良好的收率获得所介绍的染料。我们对所得到的对称小分子的光学、电化学和热学特性进行了深入研究，并证明了它们在 OLED 设备中的潜在应用性。此外，还通过实验和理论研究探讨了分子结构与性能之间的关系。由于使用了不同的供体基团，因此可以实现从绿光（DEV4）到橙红光（DEV3）的高效电致发光，其中 DEV4 的最大亮度为 3 820 cd/m2。在设计的分子中加入乙炔连接物后，D 和 A 片段可以自由旋转，从而在整个分子中实现有效的 π 电子通信，这一点已通过 DFT 研究得到证实。所获得的染料具有高热稳定性、可逆的氧化还原过程、令人满意的光电特性以及在有机溶剂中的良好溶解性等特点，非常适合应用于小分子有机发光二极管（SM-OLED）技术。