(4-乙炔基苯基)(4-吡啶基)乙炔 | 189190-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (4-乙炔基苯基)(4-吡啶基)乙炔
• 英文名称: 4-((4-ethynylphenyl)ethynyl)pyridine
• 英文别名: 4-[2-(4-Ethynylphenyl)ethynyl]pyridine
• CAS: 189190-29-2
• 化学式: C₁₅H₉N
• 分子量: 203.243
• InChiKey: QEUHXPTXFCCCBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-乙炔基苯基)(4-吡啶基)乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 35.0h， 生成 dimethyl 7'-((4-((4-(acetylthio)phenyl)ethynyl)phenyl)ethynyl)-8a'H-spiro[fluorene-9,1'-indolizine]-2',3'-dicarboxylate
  参考文献：
  名称：

  Synthesis of dihydroindolizines for potential photoinduced work function alteration

  摘要：

  Seeking to immobilize photochromophores on metallic surfaces, we have synthesized four molecules which contain both a photoresponsive dihydroindolizine (DHI) core and a sulfur containing moiety, which allow for their assembly onto gold substrates. Sonogashira, Suzuki, or Ullmann couplings are employed to generate pyridines with pendant thioacetates (or disulfides). The pyridines are condensed with spiro[2-cyclopropene-1,9'[9H]fluorene]-2,3-dimethyl ester affording the targeted DHIs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.097
• 作为产物：
  描述：

  4-((三甲基甲硅烷基)乙炔)吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 65.5h， 生成 (4-乙炔基苯基)(4-吡啶基)乙炔
  参考文献：
  名称：

  Synthesis of dihydroindolizines for potential photoinduced work function alteration

  摘要：

  Seeking to immobilize photochromophores on metallic surfaces, we have synthesized four molecules which contain both a photoresponsive dihydroindolizine (DHI) core and a sulfur containing moiety, which allow for their assembly onto gold substrates. Sonogashira, Suzuki, or Ullmann couplings are employed to generate pyridines with pendant thioacetates (or disulfides). The pyridines are condensed with spiro[2-cyclopropene-1,9'[9H]fluorene]-2,3-dimethyl ester affording the targeted DHIs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.097

文献信息

• Effect of the organic fragment on the mesogenic properties of a series of organogold(I) isocyanide complexes. X-ray crystal structure of [Au(CCC5H4N)(CNC6H4O(O)CC6H4OC10H21)]
  作者：Montserrat Ferrer、Mounia Mounir、Laura Rodríguez、Oriol Rossell、Silverio Coco、Pilar Gómez-Sal、Avelino Martín

  DOI：10.1016/j.jorganchem.2005.02.043

  日期：2005.4

  isonitrile.In addition, an unexpected ionic derivative [Au(CCC5H4NC10H21)2][Au(CCC5H4N)2] was formed in the reaction between [PPh4][Au(CCC5H4N)2] and C10H21I. All these compounds have been characterized by IR and NMR spectroscopy and mass spectrometry. The X-ray crystal structure of the compound with R = CCC5H4N shows a linear molecule in which the gold atom is surrounded by the pyridine-containing acetylene

  制备棒状有机金（I）配合物[AuR（CNC 6 H 4 O（O）CC 6 H 4 OC 10 H 21 - p）]，并研究其液晶行为。取决于R的性质，合成方法是不同的。因此，对于R =取代的炔基配体，分两个步骤制备新化合物：（i）[AuCl（tht）]（tht =四氢噻吩）与R'CCH（R'= C 5 H 4 N，C 6 H 4 CN，C 6 H 4 CCC 5 H 4 N）在NaOAc的存在下产生不溶性[Au（CCR'）] n; （ii）后者与异腈CNC 6 H 4 O（O）CC 6 H 4 OC 10 H 21 - p的反应。对于R =氟化芳基，通过从化合物[AuR（ tht）]（R = C 5 F 4 N，C 6 F 4 C 5 H 4 N，C 6 F 5）与异腈。此外，意外的离子衍生物[Au（CCC 5 H 4 NC 10 H 21）2 ] [Au（CCC第五名ħ 4 N）2 ]被形成了[PPH之间的反应4
• Investigation of Two-Photon Absorption Properties in Branched Alkene and Alkyne Chromophores
  作者：Ajit Bhaskar、Guda Ramakrishna、Zhikuan Lu、Robert Twieg、Joel M. Hales、David J. Hagan、Eric Van Stryland、Theodore Goodson

  DOI：10.1021/ja060630m

  日期：2006.9.1

  alkyne branched structures have been synthesized, and their two-photon absorption (2PA) properties are reported. This series of alkene and alkyne trimer systems tests the mechanistic approach for enhancing the 2PA process which is usually dictated by the pi-bridging, delocalization length, and corresponding charge transfer on the 2PA cross sections. The results suggest that alkene branched systems

  已经合成了新的烯烃和炔烃支链结构，并报道了它们的双光子吸收 (2PA) 特性。这一系列的烯烃和炔烃三聚体系统测试了增强 2PA 过程的机械方法，这通常由 pi 桥接、离域长度和 2PA 横截面上的相应电荷转移决定。结果表明烯烃支化系统具有更高的 2PA 截面。虽然稳态吸收和发射测量不能成功预测 2PA 截面的观察趋势，但时间分辨测量已经解释了观察到的趋势。发现，在光激发时，存在超快电荷定位到分子内电荷转移 (ICT) 状态，
• Phosphorescent self-assembled PtII tetranuclear metallocycles
  作者：Sébastien Goeb、Valentina Prusakova、Xianghuai Wang、Aurélie Vézinat、Marc Sallé、Felix N. Castellano

  DOI：10.1039/c1cc10239g

  日期：——

  A series of rigid Pt(II) diimine diacetylide complexes and their corresponding metallocyclic derivatives were synthesized through coordination-driven self-assembly. The photophysical properties of these complexes have been studied in detail, revealing exceptionally high RT phosphorescence quantum yields and lifetimes when the excited state becomes localized on the π-conjugated bridging-ligand following intramolecular charge-transfer sensitization.

  通过配位驱动的自组装合成了一系列刚性铂（II）二亚胺二乙酰配合物及其相应的金属环衍生物。对这些配合物的光物理特性进行了详细研究，结果表明，当激发态在分子内电荷转移敏化后定域在π共轭桥接配体上时，RT磷光量子产率和寿命都非常高。
• Linear ditopic acetylide gold or mercury complexes: synthesis and photophysic studies
  作者：Montserrat Ferrer、Laura Rodrı́guez、Oriol Rossell、Fernando Pina、João C Lima、Mercè Font Bardia、Xavier Solans

  DOI：10.1016/s0022-328x(03)00442-x

  日期：2003.7

  the lower triplet state. Decay times were measured at room temperature in CH2Cl2 for 1aH (1.5 μs) and in ethanol at 77 K (149 and 500 μs for compounds 1aH and 1a′, respectively). Room-temperature emission of compounds 3a and 3aH arises from the lower singlet state and phosphorescence is only observed at 77 K. Theoretical calculations on the nature and energy of singlet and triplet states corroborate

  AlkH炔烃化合物4-乙炔基吡啶（1），4-乙炔基苯甲腈（2）和（4-乙炔基苯基）（4-吡啶基）乙炔（3）与[PPh 4 ] [Au（acac）2 ]反应生成三个新的线性双中心双-炔金（I）化合物[PPH 4 ] [AU（ALK）2 ]（对于AlkH = 1，1A ;对于AlkH = 2，图2a和用于AlkH = 3，图3a）。的反应1A与两者的N-吡啶原子的甲基化过量的甲基碘的结果。类似汞（II）[Hg（Alk）2]化合物通过的锂衍生物反应而得到1，3和（4-溴苯基）（4-吡啶基）乙炔（4）与氯化汞2。所有这些化合物已通过IR和1 H-NMR光谱和质谱进行了表征。1a的X射线晶体结构表明，金原子以线性方式被两个炔烃配体包围。已报道的化合物已作为自组装合成分子多边形的基础材料进行了测试。研究了化合物的发射，测得的量子产率在0.01 < Φ <0.04的范围内。化合物1aH和1a的室温发射'
• Carbazole‐Based Tetrapodal Anchor Groups for Gold Surfaces: Synthesis and Conductance Properties
  作者：Luke J. O'Driscoll、Xintai Wang、Michael Jay、Andrei S. Batsanov、Hatef Sadeghi、Colin J. Lambert、Benjamin J. Robinson、Martin R. Bryce

  DOI：10.1002/anie.201911652

  日期：2020.1.7

  anchor groups used in fundamental conductance studies to more elaborate anchors designed with device stability in mind. This study presents a series of oligo(phenylene-ethynylene) wires with one tetrapodal anchor and a phenyl or pyridyl head group. The new anchors are designed to bind strongly to gold surfaces without disrupting the conductance pathway of the wires. Conductive probe atomic force microscopy

  随着分子规模电子学领域的成熟以及包含分子线的器件的前景变得更加可行，有必要从基础电导研究中使用的简单锚定基团发展到考虑到器件稳定性的更精细的锚定剂。这项研究提出了一系列带有一个四脚锚和一个苯基或吡啶基头部基团的低聚（亚苯基-亚乙炔基）线。新的锚固件旨在牢固地与金表面结合，而不会破坏导线的电导路径。导电探针原子力显微镜（cAFM）用于确定导线在Au-SAM-Pt和Au-SAM-石墨烯结中的自组装单层（SAMs）的电导率，由此得出每个分子的电导率。对于tolane型导线，每个分子的平均电导高达10-4。尽管与Au电极的电子耦合有限，但仍测量到37 G0（Pt）和10-3.78 G0（石墨烯），证明了这种方法的潜力。表面结合几何形状和传输性质的计算研究合理化并支持实验结果。