1,4-diiodo-2,5-bis(prop-2-ynyloxy)benzene | 798541-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-diiodo-2,5-bis(prop-2-ynyloxy)benzene
• 英文别名: 1,4-Diiodo-2,5-bis(prop-2-ynoxy)benzene
• CAS: 798541-95-4
• 化学式: C₁₂H₈I₂O₂
• 分子量: 438.003
• InChiKey: HXWKLXVRAXHFRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-diiodo-2,5-bis(prop-2-ynyloxy)benzene 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 copper(l) iodide 作用下， 以 二氯甲烷 、 邻二甲苯 为溶剂， 反应 72.0h， 生成 1-[[2,5-Bis[2-(2-methylphenyl)ethynyl]-4-[(2,3,4,5-tetraphenylphenyl)methoxy]phenoxy]methyl]-2,3,4,5-tetraphenylbenzene
  参考文献：
  名称：

  Jacketed Poly(p-phenyleneethynylene)s:  Nonaggregating Conjugated Polymers as Blue-Emitting Rods

  摘要：

  A series of dendronized poly(p-phenyleneethynylene)s were synthesized by the Pd-catalyzed coupling of a tetraphenylbenzene-substituted aromatic diiodide to 2,5-didodecyl-1,4-diethynylbenzene to form PPEs in excellent yield and high degree of polymerization. The tetraphenylbenzene-substituted monomer was obtained by a Diels-Alder reaction of a diethynylated arene with tetraphenylcyclopentadienone. The influence of the tether length (connecting the tetraphenylbenzene units to the main chain of the polymer) on the optical properties of the polymers was investigated. The closer the tetraphenylbenzene units were placed to the main chain, the larger is their effect upon the PPE's optical properties. In the case where the tether is shortest, i.e., two atoms, the optical properties of the PPE in the solid state and in solution are identical.

  DOI：

  10.1021/ma048535q
• 作为产物：
  描述：

  3-溴丙炔 、 2,5-二碘-1,4-苯二醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以95%的产率得到1,4-diiodo-2,5-bis(prop-2-ynyloxy)benzene
  参考文献：
  名称：

  Jacketed Poly(p-phenyleneethynylene)s:  Nonaggregating Conjugated Polymers as Blue-Emitting Rods

  摘要：

  A series of dendronized poly(p-phenyleneethynylene)s were synthesized by the Pd-catalyzed coupling of a tetraphenylbenzene-substituted aromatic diiodide to 2,5-didodecyl-1,4-diethynylbenzene to form PPEs in excellent yield and high degree of polymerization. The tetraphenylbenzene-substituted monomer was obtained by a Diels-Alder reaction of a diethynylated arene with tetraphenylcyclopentadienone. The influence of the tether length (connecting the tetraphenylbenzene units to the main chain of the polymer) on the optical properties of the polymers was investigated. The closer the tetraphenylbenzene units were placed to the main chain, the larger is their effect upon the PPE's optical properties. In the case where the tether is shortest, i.e., two atoms, the optical properties of the PPE in the solid state and in solution are identical.

  DOI：

  10.1021/ma048535q

文献信息

• Conjugated polyelectrolytes with galactose-containing side chains for targeted hepatoma cell imaging
  作者：Mingli Zhang、Pan Wu、Wei-Tao Dou、Hai-Hao Han、Xiao-Peng He、Chunyan Tan、Yuyang Jiang

  DOI：10.1039/c7cc02363d

  日期：——

  Three cationic conjugated polyelectrolytes (CPEs) with a common poly(p-phenylene ethynylene) backbone and different galactose-containing side chains were designed and synthesized. These CPEs were characterized and their application in targeted hepatoma cell imaging was demonstrated.

  设计并合成了具有共同的聚对苯撑乙炔基主链和不同的含半乳糖侧链的三种阳离子共轭聚电解质（CPE）。对这些CPE进行了表征，并证明了它们在靶向肝癌细胞成像中的应用。
• Synthesis, characterization, and OLED application of oligo(p-phenylene ethynylene)s with polyhedral oligomeric silsesquioxanes (POSS) as pendant groups
  作者：Vuthichai Ervithayasuporn、Junichi Abe、Xin Wang、Toshinori Matsushima、Hideyuki Murata、Yusuke Kawakami

  DOI：10.1016/j.tet.2010.10.009

  日期：2010.11

  Two new classes of mono- and oligo(p-phenylene ethynylene)s grafted with polyhedral oligomeric silsesquioxanes (POSS) were synthesized via ‘click’ chemistry and palladium-catalyzed Sonogashira cross-coupling. These materials with cubic silsesquioxanes are very robust with excellent thermal stability in air (T5%loss>330 °C) and exhibited Tg>80 °C. All the compounds showed high photoluminescence with

  通过“点击”化学和钯催化的Sonogashira交叉偶联合成了两类新的接枝有多面体低聚倍半硅氧烷（POSS）的单和低聚对亚苯基乙炔基。这些具有立方倍半硅氧烷的材料非常坚固，在空气中具有出色的热稳定性（T 5％损失> 330°C），T g > 80°C。所有化合物在溶液中均显示出高的光致发光性，并具有一定范围的蓝光发射和高达80％的量子产率。低聚的扩展π共轭分子p的PE POSS保持在固体状态下相对高的PL量子效率，相较于单- pPEs POSS。初步报道了其中一些材料为带有活性掺杂剂PVK和PBD的多层OLED组件。
• Click Chemistry as a Powerful Tool for the Construction of Functional Poly(<i>p</i><i>-</i>phenyleneethynylene)s:  Comparison of Pre- and Postfunctionalization Schemes
  作者：Brian C. Englert、Selma Bakbak、Uwe H. F. Bunz

  DOI：10.1021/ma050484p

  日期：2005.7.1

  1,3-Dipolar cycloadditions have been used to prepare a series of functionalized poly(p-phenyleneethynylene)s (PPEs). This was accomplished by employing a PPE with pendent triisopropyl-silylacetylene groups. The triisopropylsilyl groups can be removed in situ, exposing free alkynes in the side chains of the polymer to react with azides in a postpolymerization functionalization strategy in a 1,3-dipolar cycloaddition. The properties of these polymers were explored and compared to polymers of the same molecular structure but synthesized by a prepolymerization functionalization approach. Polymers of the same structure exhibit identical H-1 NMR, C-13 NMR, and IR spectra regardless of whether they were obtained by a conventional route or by postfunctionalization of a suitable PPE. UV-vis and fluorescence spectra are similar in solution. Postmodification through click chemistry, when compared to premodification, is an excellent method to produce functionalized, defect-free PPEs. Reaction of the azides with the main chain alkyne units is not observed.