4-(4-octyloxyphenylethynyl)phenylacetylene | 1162754-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-octyloxyphenylethynyl)phenylacetylene
• 英文别名: 1-ethynyl-4-((4-(octyloxy)phenyl)ethynyl)benzene；1-Ethynyl-4-[2-(4-octoxyphenyl)ethynyl]benzene；1-ethynyl-4-[2-(4-octoxyphenyl)ethynyl]benzene
• CAS: 1162754-51-9
• 化学式: C₂₄H₂₆O
• 分子量: 330.47
• InChiKey: KVPYWHYRNJMQEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  4-碘乙酰基苯酚 、 4-(4-octyloxyphenylethynyl)phenylacetylene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以97.2%的产率得到4-[4-(4-octyloxyphenylethynyl)phenylethynyl]phenyl acetate
  参考文献：
  名称：

  具有 3,3'-(4H,4'H)-Spirobi(2H-萘并[1,2-b]吡喃)骨架的旋光螺环化合物的合成及其作为向列液晶手性掺杂剂的应用

  摘要：

  用于向列液晶的具有螺结构的手性掺杂剂由光学活性的 3,3'-(4H,4'R)-螺二(2H-萘并[1,2-b]吡喃)-6,6'-二羧酸合成，并评估了它们的螺旋扭曲力 (HTP) 值。具有 S 构型的手性掺杂剂在主体向列液晶中诱导负螺旋。发现新型酯连接的螺手性掺杂剂表现出大的摩尔 HTP 值。特别是，在侧链部分具有两个嘧啶结构的手性掺杂剂显示出最高的摩尔 HTP 值，为 62.1 μm -1 mol -1 kg。相比之下，醚连接的手性掺杂剂显示出相对较小的摩尔 HTP 值。

  DOI：

  10.1246/bcsj.82.519
• 作为产物：
  描述：

  4-octyloxyphenylacetylene 在 copper(l) iodide 、 四(三苯基膦)钯 、 水 、 二异丙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成 4-(4-octyloxyphenylethynyl)phenylacetylene
  参考文献：
  名称：

  Unichromophoric Platinum-Acetylides That Contain Pentiptycene Scaffolds: Torsion-Induced Dual Emission and Steric Shielding of Dynamic Quenching

  摘要：

  The effect of the rigid bulky pentiptycene scaffolds on the photoluminescence, redox properties, and oxygen sensing behavior of unichromophoric Pt-acetylides is reported. When the pentiptycene groups are near the Pt(PBu3)(2) center, the Pt-acetylides display both blue fluorescence and green phosphorescence with long phosphorescence lifetimes (90-202 mu s) in THF. Their phosphorescence intensity is highly sensitive to molecular oxygen, and the emission color depends on the concentration of not only oxygen but also the complexes, which allows a feasible determination of oxygen in the range of 1-5% air volume. The dynamic quenching rate constants decrease linearly with increasing the number of pentiptycene groups, revealing the steric shielding effect of the peripheral rings of pentiptycene. A dependence of oxidation potential on the number of pentiptycene groups also revealed the steric shielding effect on the electron transfer between the complexes and the electrode. In a PMMA matrix, the dual emissive properties are diminished due to increased phosphorescence and decreased fluorescence intensity, and the phosphorescence lifetimes are significantly increased (up to similar to 700 mu s), leading to an "on-off" optical response to oxygen concentration. Both the dual emissive properties and long-lived triplet excitons are attributed to diminished spin-orbit couplings caused by twisting and steric shielding of the if-conjugated backbone around the Pt center.

  DOI：

  10.1021/ic4025052

文献信息

• Synthesis, characterization and DFT calculations of new ethynyl-bridged C60 derivatives
  作者：Simon Rondeau-Gagné、Carles Curutchet、François Grenier、Gregory D. Scholes、Jean-François Morin

  DOI：10.1016/j.tet.2010.03.092

  日期：2010.6

  A new series of soluble C-60 derivatives for organic electronic application has been synthesized by ethynylation reaction using different electron-donating and electron-withdrawing groups of varying length. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Optically Active Spiro Compounds with a 3,3′-(4<i>H</i>,4′<i>H</i>)-Spirobi(2<i>H</i>-naphtho[1,2-<i>b</i>]pyran) Skeleton and Their Applications as Chiral Dopants for Nematic Liquid Crystals
  作者：Kenta Tojo、Tatsuya Arisawa、Yoshio Aoki、Daiyo Terunuma

  DOI：10.1246/bcsj.82.519

  日期：2009.3.15

  Chiral dopants with a spiro structure for nematic liquid crystals were synthesized from optically active 3,3'-(4H,4'R)-spirobi(2H-naphtho[1,2-b]pyran)-6,6'-dicarboxylic acid, and their helical twisting power (HTP) values were evaluated. Chiral dopants having the S configuration induced minus helices in the host nematic liquid crystals. It was found that the novel ester-linked spiro chiral dopants exhibited

  用于向列液晶的具有螺结构的手性掺杂剂由光学活性的 3,3'-(4H,4'R)-螺二(2H-萘并[1,2-b]吡喃)-6,6'-二羧酸合成，并评估了它们的螺旋扭曲力 (HTP) 值。具有 S 构型的手性掺杂剂在主体向列液晶中诱导负螺旋。发现新型酯连接的螺手性掺杂剂表现出大的摩尔 HTP 值。特别是，在侧链部分具有两个嘧啶结构的手性掺杂剂显示出最高的摩尔 HTP 值，为 62.1 μm -1 mol -1 kg。相比之下，醚连接的手性掺杂剂显示出相对较小的摩尔 HTP 值。
• Unichromophoric Platinum-Acetylides That Contain Pentiptycene Scaffolds: Torsion-Induced Dual Emission and Steric Shielding of Dynamic Quenching
  作者：Che-Jen Lin、Chih-Yuan Chen、Sandip Kumar Kundu、Jye-Shane Yang

  DOI：10.1021/ic4025052

  日期：2014.1.21

  The effect of the rigid bulky pentiptycene scaffolds on the photoluminescence, redox properties, and oxygen sensing behavior of unichromophoric Pt-acetylides is reported. When the pentiptycene groups are near the Pt(PBu3)(2) center, the Pt-acetylides display both blue fluorescence and green phosphorescence with long phosphorescence lifetimes (90-202 mu s) in THF. Their phosphorescence intensity is highly sensitive to molecular oxygen, and the emission color depends on the concentration of not only oxygen but also the complexes, which allows a feasible determination of oxygen in the range of 1-5% air volume. The dynamic quenching rate constants decrease linearly with increasing the number of pentiptycene groups, revealing the steric shielding effect of the peripheral rings of pentiptycene. A dependence of oxidation potential on the number of pentiptycene groups also revealed the steric shielding effect on the electron transfer between the complexes and the electrode. In a PMMA matrix, the dual emissive properties are diminished due to increased phosphorescence and decreased fluorescence intensity, and the phosphorescence lifetimes are significantly increased (up to similar to 700 mu s), leading to an "on-off" optical response to oxygen concentration. Both the dual emissive properties and long-lived triplet excitons are attributed to diminished spin-orbit couplings caused by twisting and steric shielding of the if-conjugated backbone around the Pt center.