9H-咔唑,9-十四烷基-3,6-二[(三甲基甲硅烷基)乙炔基]- | 197860-65-4

• 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
• 中文名称: 9H-咔唑,9-十四烷基-3,6-二[(三甲基甲硅烷基)乙炔基]-
• 英文名称: 3,6-bis[(trimethylsilyl)ethynyl]-9-tetradecylcarbazole
• 英文别名: 9-Tetradecyl-3,6-bis[(trimethylsilyl)ethynyl]-9H-carbazole；trimethyl-[2-[9-tetradecyl-6-(2-trimethylsilylethynyl)carbazol-3-yl]ethynyl]silane
• CAS: 197860-65-4
• 化学式: C₃₆H₅₃NSi₂
• 分子量: 555.995
• InChiKey: VICQHKPHJDMRIS-UHFFFAOYSA-N

物化性质

• 沸点：
  581.4±50.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.95
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  9H-咔唑,9-十四烷基-3,6-二[(三甲基甲硅烷基)乙炔基]- 在 四(三苯基膦)钯 sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 49.0h， 生成 3,6-Bis(3'-iodo-9'-tetradecylcarbazolyl)-9-tetradecylcarbazole
  参考文献：
  名称：

  Syntheses of Novel Carbazolylacetylene-Derived Macrocycles

  摘要：

  本文介绍了基于咔唑基乙炔单元的新型环状低聚物的合成。在高稀释条件下，3,6-二乙炔基-9-十四烷基咔唑和 3,6-双（3'-碘-9'-十四烷基咔唑基）-9-十四烷基咔唑在钯(PPh3)4/CuI 催化剂存在下发生反应，合成出所需的环状四聚体，收率为 14.3%。除四聚体外，还分离出一种环状八聚体，产率为 5.4%。

  DOI：

  10.1055/s-2001-17518
• 作为产物：
  描述：

  溴代十四烷 在 N-碘代丁二酰亚胺 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.33h， 生成 9H-咔唑,9-十四烷基-3,6-二[(三甲基甲硅烷基)乙炔基]-
  参考文献：
  名称：

  Syntheses of Novel Carbazolylacetylene-Derived Macrocycles

  摘要：

  本文介绍了基于咔唑基乙炔单元的新型环状低聚物的合成。在高稀释条件下，3,6-二乙炔基-9-十四烷基咔唑和 3,6-双（3'-碘-9'-十四烷基咔唑基）-9-十四烷基咔唑在钯(PPh3)4/CuI 催化剂存在下发生反应，合成出所需的环状四聚体，收率为 14.3%。除四聚体外，还分离出一种环状八聚体，产率为 5.4%。

  DOI：

  10.1055/s-2001-17518

文献信息

• Electroluminescent applications of a cyclic carbazole oligomer
  作者：Sumio Maruyama、Xu-tang Tao、Hirofumi Hokari、Taeyong Noh、Yadong Zhang、Tatsuo Wada、Hironori Suzuki、Toshiyuki Watanabe、Seizo Miyata

  DOI：10.1039/a809313j

  日期：——

  A cyclic carbazole oligomer for organic light-emitting diodes is described. This cyclic oligomer has a high glass transition temperature (105 °C), and high quality amorphous film can be prepared by the conventional spin-coating technique. We examined the characteristics of this cyclic oligomer for electron transport layer applications. The device structure of indium tin oxide/hole transport layer/electron transport layer/Al was used. The EL device exhibited green light with a luminance of 60 cd m –2 at 15 V and the external quantum efficiency was 0.44%.

  本文介绍了一种用于有机发光二极管的环状咔唑低聚物。这种环状低聚物具有较高的玻璃化转变温度（105 °C），可以通过传统的旋涂技术制备出高质量的无定形薄膜。我们研究了这种环状低聚物在电子传输层应用方面的特性。我们采用了氧化铟锡/空穴传输层/电子传输层/铝的器件结构。电致发光器件在 15 V 电压下发出亮度为 60 cd m -2 的绿光，外部量子效率为 0.44%。
• Arylene Ethynylene Macrocycles Prepared by Precipitation-Driven Alkyne Metathesis
  作者：Wei Zhang、Jeffrey S. Moore

  DOI：10.1021/ja046531v

  日期：2004.10.1

  A convenient, multigram-scale synthesis of arylene ethynylene macrocycles near room temperature is described. Driven by the precipitation of a diarylacetylene byproduct, alkyne metathesis produces the desired macrocycles in one step from monomers in high yields.
• Engineering Solid-State Morphologies in Carbazole–Ethynylene Macrocycles
  作者：Aaron D. Finke、Dustin E. Gross、Amy Han、Jeffrey S. Moore

  DOI：10.1021/ja204795q

  日期：2011.9.7

  We present a crystallographic study that systematically investigates the effects of the n-alkyl side-chain length on the crystal packing in shape-persistent macrocycles. The solid-state packing of carbazole-ethynylene-containing macrocycles is sensitive to the alkyl-chain length. In macrocycles containing n-alkyl side chains up to nine carbons in length, face-on aromatic. pi interactions predominate, while the addition of one carbon leads to a completely different packing arrangement. Macrocycles with C-10 or C-11 chains exhibit a novel packing motif wherein the alkyl chains intercalate between macrocycles, leading in one case to continuous solvent-filled channels. When crystals of the C-10 macrocycle are bathed in solvent, the included molecules exchange with the external solvent, and the alkyl chain disorder changes in response to changes in the guest volume in order to retain crystallinity. Powder X-ray diffraction data indicate that alkyl-macrocycle interactions in the longer chains "emulate" the distances typical of face-to-face pi interactions, leading to deceptive indicators of pi stacking.
• PREPARATION OF A CARBAZOLE-BASED MACROCYCLE VIA PRECIPITATION-DRIVEN ALKYNE METATHESIS
  作者：Zhang, Wei、Cho, Hyeon Mo、Moore, Jeffrey S.、Denmark, Scott E.、Butler, Christopher R.

  DOI：10.15227/orgsyn.084.0177

  日期：——
• Syntheses of Novel Carbazolylacetylene-Derived Macrocycles
  作者：Sumio Maruyama、Hirofumi Hokari、Tatsuo Wada、Hiroyuki Sasabe

  DOI：10.1055/s-2001-17518

  日期：——

  The syntheses of novel cyclic oligomers based on the carbazolylacetylene unit are described. The desired cyclic tetramer could be synthesized in 14.3% yield by the reaction of 3,6-diethynyl-9-tetradecylcarbazole and 3,6-bis(3’-iodo-9’-tetradecylcarbazolyl)-9-tetradecylcarbazole in the presence of Pd(PPh3)4/CuI as catalysts under high dilution conditions and purified by column chromatography and isolated by preparative gel permeation chromatography. Besides the tetramer, a cyclic octamer was also isolated in 5.4% yield.

  本文介绍了基于咔唑基乙炔单元的新型环状低聚物的合成。在高稀释条件下，3,6-二乙炔基-9-十四烷基咔唑和 3,6-双（3'-碘-9'-十四烷基咔唑基）-9-十四烷基咔唑在钯(PPh3)4/CuI 催化剂存在下发生反应，合成出所需的环状四聚体，收率为 14.3%。除四聚体外，还分离出一种环状八聚体，产率为 5.4%。