1-ethynyl-4-nonylbenzene | 123501-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-ethynyl-4-nonylbenzene
• 英文别名: 4-nonylphenyl-acetylene
• CAS: 123501-86-0
• 化学式: C₁₇H₂₄
• 分子量: 228.378
• InChiKey: FBTDGSIIZWDHBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-ethynyl-4-nonylbenzene 在 四甲基乙二胺 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 生成 1-Nonyl-4-[4-(4-nonylphenyl)buta-1,3-diynyl]benzene
  参考文献：
  名称：

  Synthesis of diphenyl-diacetylene-based nematic liquid crystals and their high birefringence properties

  摘要：

  我们合成了两系列基于二苯二炔（DPDA）的材料，分别为具有不同长度的烷氧基和烷基尾（DPDA–OCm和DPDA–Cm），并测量它们在不同波长和温度下的向列相双折射率（Δn）。我们发现，随着m的增加，Δn呈下降趋势，这可能是由于低Δn烷基尾的稀释效应。此外，在两组材料中，DPDA–OCm材料的Δn相对较高，在接近各向同性到向列相转变温度的10°C时，DPDA–OC1在550 nm处的Δn达到了最高值0.4。此外，我们观察到了Δn的温度依赖性，它与有序参数（s）成正比。从对s = 1（完美取向状态）的外推来看，可以推测DPDA–O基团具有提供非常大的Δn（0.9）的潜力。

  DOI：

  10.1039/c2jm16002a
• 作为产物：
  描述：

  4-正壬基苯乙酮 在 五氯化磷 、 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 生成 1-ethynyl-4-nonylbenzene
  参考文献：
  名称：

  Chemically-Induced Discotic Liquid Crystals. Structural Studies with Nmr Spectroscopy

  摘要：

  Deuterium NMR spectroscopy provides an especially important technique with which to investigate a wide range of liquid crystal behaviour. Here, we describe its use in the structural study of liquid crystals formed from discotic or disc-like molecules and, to illustrate the breadth and power of the NMR method, we have selected two systems in which the liquid crystal phases are chemically induced. The binary mixtures are similar in that one component is a radial multiyne but differ significantly in the nature of the chemical inductor. In one case the inductor is a nitrated fluorenone which has a similar anisotropy to the radial multiyne while for the second system the inductor, a substituted o-xylene is considerably smaller and far less anisotropic. By measuring the deuterium NMR spectra of suitably deuteriated versions of the components we show how it is possible to investigate the orientational order of the components in the various induced phases, their effective molecular symmetry, the molecular geometry, the chain flexibility and orientational order together with the phase symmetry. The results of these investigations are described and explained.

  DOI：

  10.1080/15421400390213311

文献信息

• Dianthraceno[a,e]pentalenes: synthesis, crystallographic structures and applications in organic field-effect transistors
  作者：Gaole Dai、Jingjing Chang、Wenhua Zhang、Shiqiang Bai、Kuo-Wei Huang、Jianwei Xu、Chunyan Chi

  DOI：10.1039/c4cc07630c

  日期：——

  Two stable dianthraceno[a,e]pentalenes were synthesized and DAP2 exhibited a high charge carrier mobility of 0.65 cm² V⁻¹ s⁻¹ due to its dense packing.

  合成了两种稳定的二蒽[a,e]五环烯，并且由于其密集的堆积，DAP2 表现出高达0.65 cm² V⁻¹ s⁻¹的载流子迁移率。
• Catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts in water
  作者：Nikolai A. Bumagin、Ludmila I. Sukhomlinova、Elena V. Luzikova、Tatiana P. Tolstaya、Irina P. Beletskaya

  DOI：10.1016/0040-4039(95)02255-4

  日期：1996.2

  The catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts are shown to occur in aqueous K2CO3 in the presence of 10 mol.% Bu3N under very mild conditions using PdCl2(PPh3)2 and CuI as catalyst precursor to give substituted tolans in high yields.

  结果表明，在非常温和的条件下，使用PdCl 2（PPh 3）2和CuI作为催化剂的前体，末端乙炔与碘芳烃和二芳基碘鎓盐的催化偶合在K 2 CO 3水溶液中在10 mol。％Bu 3 N的存在下发生。以高收率得到取代的tolan。
• Thienoacene-Fused Pentalenes: Syntheses, Structures, Physical Properties and Applications for Organic Field-Effect Transistors
  作者：Gaole Dai、Jingjing Chang、Xueliang Shi、Wenhua Zhang、Bin Zheng、Kuo-Wei Huang、Chunyan Chi

  DOI：10.1002/chem.201405652

  日期：2015.1.26

  their unique electronic absorption spectra. These new compounds exhibited good thermal stability and ordered packing in solid state and thus their applications in organic field‐effect transistors (OFETs) were also investigated. The highest field‐effect hole mobility of 0.016, 0.036 and 0.001 cm2 V−1 s−1 was achieved for solution‐processed thin films of 1–3, respectively.

  三可溶且稳定thienoacene稠合并环戊二烯衍生物（1 - 3合成了不同的π共轭长度。X射线晶体学分析和密度泛函理论（DFT）计算表明，由于芳族硫杂并苯并苯单元与抗芳族戊烯部分之间的相互作用，它们具有独特的几何和电子结构。结果，它们都具有小的能隙并且显示出两性氧化还原行为。时间依赖性（TD）DFT计算用于解释其独特的电子吸收光谱。这些新化合物表现出良好的热稳定性，并在固态下有序堆积，因此，还研究了它们在有机场效应晶体管（OFET）中的应用。最高场效应空穴迁移率为0.016、0.036和0.001 cm 2  V -1  s -1对于固溶处理的1到3层薄膜，分别获得了1-5％的结果。
• Bumagin; Sukhomlinova; Luzikova, Russian Journal of Organic Chemistry, 1996, vol. 32, # 7, p. 996 - 1000
  作者：Bumagin、Sukhomlinova、Luzikova、Tolstaya、Beletskaya

  DOI：——

  日期：——
• Phenyl dialkynylcarbinols, a Bioinspired Series of Synthetic Antitumor Acetylenic Lipids
  作者：Margaux Bossuat、Pauline Rullière、Nadège Preuilh、Antonio Peixoto、Etienne Joly、Jean-Guillaume Gomez、Maroua Bourkhis、Frédéric Rodriguez、Fernanda Gonçalves、Isabelle Fabing、Hafida Gaspard、Vania Bernardes-Génisson、Valérie Maraval、Stéphanie Ballereau、Remi Chauvin、Sébastien Britton、Yves Génisson

  DOI：10.1021/acs.jmedchem.3c00859

  日期：2023.10.26