(4-hexadecyloxy)phenylacetylene | 318472-41-2

• 英文名称: (4-hexadecyloxy)phenylacetylene
• 英文别名: 1-ethynyl-4-(hexadecyloxy)benzene；1-Ethynyl-4-hexadecoxybenzene
• CAS: 318472-41-2
• 化学式: C₂₄H₃₈O
• 分子量: 342.565
• InChiKey: JKBQZBZVXPURSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-二溴-4-甲基噻唑 、 (4-hexadecyloxy)phenylacetylene 在 copper(l) iodide 、 四(三苯基膦)钯 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以86%的产率得到2,5-bis[(4-hexadecyloxyphenyl)ethynyl]-4-methylthiazole
  参考文献：
  名称：

  Synthesis of Liquid Crystals with Bent-Rod Structure: 4-Methylthiazole Derivatives with Nematic Phase

  摘要：

  Liquid-crystalline 2,5-diarylethynyl-4-methylthiazole derivatives with bent-rod structures were prepared by a palladium-catalyzed cross-coupling reaction. The 2,5-diarylethynyl-4-methylthiazole derivatives prepared in the present study exhibit only the nematic phase.

  DOI：

  10.1080/10587250108030012
• 作为产物：
  描述：

  溴代十六烷 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 (4-hexadecyloxy)phenylacetylene
  参考文献：
  名称：

  Synthesis and Mesomorphic Properties of Some Fluorinated Benzoate Liquid Crystals

  摘要：

  Three series of [4-(4'-n-alkyloxyphenyl)acetylenyl]-2,6-difluorophenyl fluorinated benezoates and one series of fluorinated benzoates with 2,3,5,6-tetrafluorophenylene group and semi-perfluorocarbon chain have been synthesized. Their phase transition temperatures have been measured by texture observation in a polarizing microscope and confirmed by DSC. For the series without fluorocarbon chains, increasing the quantity of fluorosubstituents on the terminal phenyl groups decreased nematic stability (TN-1), but the breadth of the SmA phase range was increased. Lateral fluorosubstitution in the central group lowered the nematic stability (TN-1) and decreased the breadth of the SmA phase range. The series with semiperfluorocarbon chains were more likely to form SmA phases than the series with hydrogencarbon chains, and with the increasing of fluorosubstituents quantity on the terminal phenyl groups nematic and SmA stability (T(N-)1 and TSmA-N) were both decreased.

  DOI：

  10.1080/10587250210534

文献信息

• A New Class of Star-Shaped Discotic Liquid Crystal Containing a 2, 4, 6-Triphenyl-1, 3, 5-triazine Unit as a Core
  作者：Chi-Han Lee、Takakazu Yamamoto

  DOI：10.1246/bcsj.75.615

  日期：2002.3

  A new class of discotic liquid crystals based on 2, 4, 6-triphenyl-1, 3, 5-triazine as a core and [(4-alkoxyphen-yl)ethynyl] benzene ester as rigid arms has been synthesized by a Pd(0)/Cu(I)-catalyzed carbon–carbon coupling reaction. The obtained compounds exhibited liquid-crystalline properties.

  以2, 4, 6-三苯基-1, 3, 5-三嗪为核心，以[(4-烷氧基苯-基)乙炔基]苯酯为刚性臂的新型盘状液晶由Pd( 0)/Cu(I)-催化的碳-碳偶联反应。所得化合物表现出液晶性质。
• Synthesis of Pyrene-based Planar Conjugated Polymers and the Regioisomers by Intramolecular Cyclization
  作者：Xiaoyan Zhu、Yonggang Wu、Lina Zhou、Yuan Wang、Hongchi Zhao、Baoxiang Gao、Xinwu Ba

  DOI：10.1002/cjoc.201400793

  日期：2015.4

  easily formed in LP3. The planar conjugated polymers and model compounds show untypical features of ladder‐type polymers, they display broad absorption and blue or blue‐green emission in solution, and interchain π‐π stacking in film still occurs. Moreover, the new polymers and model compounds are characterized by nuclear magnetic resonance (NMR) spectroscopy, gel‐permeation chromatography (GPC) and cyclic

  合成了几种平面的含polymers单元的共轭聚合物和模型化合物。前体聚合物和模型化合物是通过Pd（0）催化的Suzuki反应获得的，然后在存在酸的情况下通过分子内环化形成平面结构。我们通过使用模型化合物，这表明调查分子内环化反应的区域异构体顺式-和反-structures在阶梯型聚合物形成LP1，并且顺式更容易在形成-结构LP3。平面共轭聚合物和模型化合物显示梯型聚合物的非典型特征，它们在溶液中显示出广泛的吸收和蓝或蓝绿色发射，并且膜中仍存在链间π-π堆积。此外，新型聚合物和模型化合物的特征在于核磁共振波谱，凝胶渗透色谱法和循环伏安法。
• Zipping and unzipping monolayers: switchable monolayer oligomerization and adhesion <i>via</i> thiol–disulfide interconversion
  作者：Jian He、Kyle J. Myerson、Matthew B. Zimmt

  DOI：10.1039/c7cc07846c

  日期：——

  Triphenyleneethynylene (TPE) monolayers at the solution–HOPG interface are oligomerized by the oxidation of pendant thioethers to form disulfide cross-links. The oligomerized TPE monolayer adheres strongly to HOPG. Disulfide reduction unzips the oligomers to form a monomeric TPE monolayer with pendant thiols. Subsequent oxidation and reduction treatments zip and unzip the monolayer.

  溶液-HOPG界面上的三亚苯基乙炔基（TPE）单层通过侧基硫醚的氧化反应形成二硫键交联而低聚。寡聚的TPE单层牢固地粘附在HOPG上。二硫化物还原使低聚物解压缩，形成带有侧基硫醇的单体TPE单层。随后的氧化和还原处理将单层拉链拉开。
• Reactive two-component monolayers template bottom-up assembly of nanoparticle arrays on HOPG
  作者：Chen Fang、Hua Zhu、Ou Chen、Matthew B. Zimmt

  DOI：10.1039/c8cc04058c

  日期：——

  Two triphenyleneethynylene derivatives, 1OH and 2, self-assemble a patterned monolayer (ML) at the solution–graphite (HOPG) interface. The monolayer is used to template bottom-up self-assembly of a 5 nm/19 nm double pitch pattern of gold nanoparticles on HOPG.

  两种三苯基乙炔衍生物，1OH和2，在溶液-石墨(HOPG)界面自组装成有图案的单分子层(ML)。该单分子层用于模板自下而上在HOPG上自组装5 nm/19 nm双步距金纳米颗粒的形成。
• Design and investigation of calamitic liquid crystals with low aspect-ratios: rigid y-shaped 1,2,4-tris(4-alkoxyphenylethynyl)benzenes
  作者：Hsiu-Fu Hsu、Hsin-Chou Chen、Chung-Hao Kuo、Bo-Cheng Wang、Hsien-Tai Chiu

  DOI：10.1039/b511530b

  日期：——

  The synthesis and characterization of triynylbenzenes, 1-iodo-2,4,5-tri(4-alkoxyphenylethynyl)benzenes (1), are reported, and their structure–mesomorphism relationship is investigated. These compounds possess a y-shaped geometry with rigid linear spacers and a stable nematic phase that was achieved by lengthening the alkoxy chains or replacing the iodo group with a smaller atom. The low aspect ratios and identified calamitic nature of these rigid y-shaped liquid crystals make them suitable as potential candidates to be used in the liquid crystal layer of liquid crystal display devices for improving viewing angles. In addition, the geometry of 1 was modified stepwise from a rigid y-geometry to a rigid rectangle for realization of the unstable nematic behaviors of the previously reported board-like 1,2,4,5-tetrakis(4-tridecyloxyphenylethynyl)benzene that was expected to potentially show biaxial nematic phases. The sizes of the fourth side-arm and hence the aspect ratios of these tetra-substituted benzenes are ascribed to the less liquid crystallinity.

  报告了 1-碘-2,4,5-三(4-烷氧基苯乙炔基)苯 (1) 三炔基苯的合成和表征，并研究了它们的结构-同构关系。通过延长烷氧基链或用较小的原子取代碘基，这些化合物具有带有刚性线性间隔的 Y 形几何形状和稳定的向列相。这些刚性 y 型液晶的低纵横比和确定的钙钛矿性质使它们适合作为液晶显示设备液晶层的潜在候选材料，以改善视角。此外，1 的几何形状也从刚性 y 形逐步修改为刚性矩形，以实现之前报道的板状 1,2,4,5-四(4-十三烷氧基苯乙炔基)苯的不稳定向列行为，这种不稳定向列行为有望显示出双轴向列相。第四侧臂的尺寸以及这些四取代苯的长宽比都归因于较低的液态结晶度。