3,6-diethynyl-9-hexyl-9H-carbazole | 156972-68-8

• 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-diethynyl-9-hexyl-9H-carbazole
• 英文别名: 3,6-diethynyl-9-hexylcarbazole；N-hexyl-3,6-diethynylcarbazole
• CAS: 156972-68-8
• 化学式: C₂₂H₂₁N
• 分子量: 299.415
• InChiKey: JOBIZPQIJRPBRP-UHFFFAOYSA-N

物化性质

• 沸点：
  420.2±38.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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-diethynyl-9-hexyl-9H-carbazole 、 4-苯甲酰-4`-溴联苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Engineering Solid-State Morphologies in Carbazole–Ethynylene Macrocycles

  摘要：

  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.

  DOI：

  10.1021/ja204795q
• 作为产物：
  描述：

  9-hexyl-3,6-bis((trimethylsilyl)ethynyl)-9H-carbazole 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95.6%的产率得到3,6-diethynyl-9-hexyl-9H-carbazole
  参考文献：
  名称：

  N-取代咔唑的新型钌和铱配合物作为三重态光敏剂

  摘要：

  合成了带有修饰的咔唑部分的新型单核和双核Ru（II）和Ir（III）配合物。与它们的单核类似物相比，其中含咔唑的配体起桥作用的同核双原子络合物（RuCRu和IrClr）在可见光区域显示出增加的吸收，并产生更高的单重态氧量子产率。

  DOI：

  10.1039/c7cc08535d

文献信息

• Multi-photon properties in various condensed phases of dendritic chromophores derived from carbazole and indenoquioxaline units: Synthesis and characterization
  作者：Tzu-Chau Lin、Wei Chien、Shu-Wen Dai、Hao-Wu Lin、Yueh-Ching Liu

  DOI：10.1016/j.dyepig.2019.04.044

  日期：2019.9

  We have used functionalized carbazoles and indenoquonoxalines as the main building units and enthynyl groups as the π-linkages to construct two novel dendritic fluorophores and studied their degenerate multi-photon absorption properties in both the solution phase and the neat-film state within femtosecond and nanosecond regions. In our experiments, these model compounds are found to manifest strong

  我们已经使用功能化的咔唑和茚并喹喔啉作为主要的构建单元，并使用乙炔基作为π键来构建两个新颖的树枝状荧光团，并研究了它们在溶液相以及飞秒和纳秒内的纯膜状态下的简并多光子吸收特性。地区。在我们的实验中，发现这些模型化合物对近红外区域的超短激光脉冲表现出强烈且广泛分散的双光子吸收以及有效的功率限制特性。另外，两种生色团均显示中等至强的三光子诱导的荧光，表明这种支架可作为开发三光子材料的参考结构基序。
• Siloles and Acetenyl Aromatics Copolymers: Synthesis, Characterization and Photophysical Properties
  作者：Zhenhua He、Guoqiao Lai、Zhifang Li、Xiao Yuan、Yongjia Shen、Chengyun Wang

  DOI：10.1002/cjoc.201400870

  日期：2015.5

  of the copolymers were characterized by NMR, FT‐IR techniques. Their thermal and photophysical properties were evaluated by TGA, DSC, UV‐Vis and fluorescence spectroscopy, respectively. The weight‐averaged molecular weights (Mw) of PS‐DyCz and PS‐DyF are 1.20×104 and 3.83×104 Da, respectively. The degree of polymerization is 8 and 22 units. These π‐conjugated polymers exhibited lower band‐gap of 2.25

  两种共聚物，聚（1,1-二甲基-3,4-二苯基甲硅烷基-alt- N-己基-3,6-二乙炔基咔唑）（PS-DyCz）和聚（1,1-二甲基-3,4-二苯基甲硅烷基-alt通过2,5-二溴-1,1-二甲基-3,4-二苯基甲硅烷基和N-己基-3的Sonogashira偶联反应合成了-2,7-二乙炔基-9,9'-二己基芴（PS-DyF）分别为6，二乙炔基咔唑或2,7二乙炔基9,9'二己基芴。通过NMR，FT-IR技术表征共聚物的化学结构。通过TGA，DSC，UV-Vis和荧光光谱分别评估了它们的热和光物理性质。PS-DyCz和PS-DyF的重均分子量（M w）为1.20×10 4和3.83×10 4分别在那儿。聚合度为8和22个单位。这些π共轭聚合物的骨架中存在硅环和CC三键，因此带隙较低，为2.25 eV和2.70 eV，其结果与B3LYP / 6-31G的密度泛函（DFT）计算结果一致* 等级。
• Cyclic [2]Catenane Dimers, Trimers, and Tetramers
  作者：Yi‐Wei Wu、Shun‐Te Tung、Chien‐Chen Lai、Yi‐Hung Liu、Shie‐Ming Peng、Sheng‐Hsien Chiu

  DOI：10.1002/anie.201505903

  日期：2015.9.28

  Dimeric, trimeric, and tetrameric cyclic [2]catenanes have been prepared directly through one‐pot sodium‐ion‐templated dynamic imine formation from a diamine and a tetraaldehyde. NaBH4 mediated reduction of the labile imino bonds of these cyclic [2]catenane oligomers, followed by methylation of the resulting secondary amino groups enabled the isolation and characterization of oligomeric cyclic [2]catenanes

  二聚，三聚和四聚环状[2]儿茶酚烷是通过一锅钠离子模板法由二胺和四醛动态形成亚胺而直接制备的。NaBH 4介导的使这些环状[2]环烷低聚物的不稳定亚氨基键还原，然后对所得仲氨基进行甲基化，从而能够将低聚环状[2]邻苯二酚作为稳定的，共价连接的化合物进行分离和表征。
• Breaking Radial Dipole Symmetry in Planar Macrocycles Modulates Edge‐to‐Edge Packing and Disrupts Cofacial Stacking
  作者：Yan Li、Henry D. Castillo、James R. Dobscha、Amanda R. Morgan、Steven L. Tait、Amar H. Flood

  DOI：10.1002/chem.202302946

  日期：2024.2.7

  Dipolar interactions are ever‐present in supramolecular architectures, though their impact is typically revealed by making dipoles stronger. While it is also possible to assess the role of dipoles by altering their orientations by using synthetic design, doing so without altering the molecular shape is not straightforward. We have now done this by flipping one triazole unit in a rigid macrocycle, tricarb. The macrocycle is composed of three carbazoles (2 Debye) and three triazoles (5 Debye) defining an array of dipoles aligned radially but organized alternately in and out. These dipoles are believed to dictate edge‐to‐edge tiling and face‐to‐face stacking. We modified our synthesis to prepare isosteric macrocycles with the orientation of one triazole dipole rotated 40°. The new dipole orientation guides edge‐to‐edge contacts to reorder the stability of two surface‐bound 2D polymorphs. The impact on dipole‐enhanced π stacking, however, was unexpected. Our stacking model identified an unchanged set of short‐range (3.4 Å) anti‐parallel dipole contacts. Despite this situation, the reduction in self‐association was attributed to long‐range (~6.4 Å) dipolar repulsions between π‐stacked macrocycles. This work highlights our ability to control the build‐up and symmetry of macrocyclic skeletons by synthetic design, and the work needed to further our understanding of how dipoles control self‐assembly.

  摘要 双极相互作用在超分子结构中无处不在，但其影响通常是通过使偶极子变得更强来揭示的。虽然也可以通过合成设计改变偶极子的取向来评估偶极子的作用，但在不改变分子形状的情况下这样做并不简单。现在，我们通过翻转刚性大环--三碳化合物--中的一个三唑单元实现了这一目的。这个大环由三个咔唑（2 Debye）和三个三唑（5 Debye）组成，形成了一个径向排列但内外交替的偶极子阵列。据信，这些偶极子决定了边到边的堆积和面对面的堆积。我们修改了合成方法，制备出将一个三唑偶极子的取向旋转 40°的同位大环。新的偶极子取向引导边到边接触，重新安排了两种表面结合二维多晶体的稳定性。然而，这对偶极子增强 π 堆积的影响却出乎意料。我们的堆叠模型确定了一组不变的短程（3.4 Å）反平行偶极接触。尽管如此，自结合的减少还是归因于π堆叠大环之间的长程（约 6.4 Å）偶极斥力。这项工作凸显了我们通过合成设计控制大环骨架的堆积和对称性的能力，以及进一步了解偶极如何控制自组装所需的工作。
• Fluorene compound, polymers thereof having a polyphenylene group, and EL element comprising the same
  申请人：Korea Institute of Science and Technology

  公开号：US20030099838A1

  公开（公告）日：2003-05-29

  A fluorene compound and polymers thereof having a polyphenylene group, and EL element comprising the same, which can be prepared through a Diels-Alder reaction of a compound having one or more cyclopentadienone group and a compound having one or more acetylene group and can be used as a core material for organic and polymeric EL element and/or other optical devices.

  通过具有一个或多个环戊二烯酮基团的化合物与具有一个或多个炔基团的化合物的 Diels-Alder 反应，可制备具有聚苯基团的芴化合物及其聚合物，以及由其组成的 EL 元件，该元件可用作有机和聚合物 EL 元件和/或其他光学器件的核心材料。