1,5-bis[(3,5-bis-trimethylsilylethynylphenyl)ethynyl]naphthalene | 599187-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-bis[(3,5-bis-trimethylsilylethynylphenyl)ethynyl]naphthalene
• 英文别名: 2-[3-[2-[5-[2-[3,5-bis(2-trimethylsilylethynyl)phenyl]ethynyl]naphthalen-1-yl]ethynyl]-5-(2-trimethylsilylethynyl)phenyl]ethynyl-trimethylsilane
• CAS: 599187-71-0
• 化学式: C₄₆H₄₈Si₄
• 分子量: 713.229
• InChiKey: VAQVAFRIHWHSLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.55
• 重原子数：
  50.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,5-bis[(3,5-bis-trimethylsilylethynylphenyl)ethynyl]naphthalene 在 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 1,5-bis[2-(3,5-diethynylphenyl)ethynyl]naphthalene
  参考文献：
  名称：

  Synthesis of nanostructures based on 1,4- and 1,3,5-phenylethynyl units with π-extended conjugation. Carbon networks dendrimer base units

  摘要：

  A convenient and efficient synthesis of 3,5-di(silylethynyl)phenylacetylene and p-[3,5-di(silylethynyl)phenylethynyl]phenylacetylene has been carried out. These compounds serve to prepare nanometer-sized conjugated 1,4- and 1,3,5-phenylethynyl oligomers, by means of cross-coupling with a convenient haloaryl derivative, catalysed by palladium(H), in excellent yields. The phenylethynyl homologues show fluorescence emission, the wavelength of which is displaced by approximately 20 nm by each phenylethynyl unit increasing the conjugate chain. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01137-7
• 作为产物：
  描述：

  1,3,5-三溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 46.0h， 生成 1,5-bis[(3,5-bis-trimethylsilylethynylphenyl)ethynyl]naphthalene
  参考文献：
  名称：

  基于1,4-和1,3,5-乙炔基苯基亚基的pi扩展共轭合成纳米结构。碳树突单元。

  摘要：

  从3,5-二（三甲基甲硅烷基乙炔基）苯基乙炔和对-[3,5-二（三甲基甲硅烷基乙炔基）-1-乙炔基苯基]苯基乙炔开始，合成了纳米级共轭的1,4-和1,3,5-乙炔基苯基低聚物。钯（II）/铜（I）催化的方便卤代芳基衍生物交叉偶联反应，收率很高。通过特定的保护-脱保护方法有效地制备了末端乙炔。所获得的所有乙炔基苯基同系物均显示出荧光发射，每个乙炔基苯基单元的红移大约为20 nm，从而增加了共轭链。通过插入1，5-萘亚单元制备平行的共轭乙炔基苯基链，并且该化合物表现出荧光辐射发射。

  DOI：

  10.1021/jo034972b

文献信息

• Synthesis of Nanostructures Based on 1,4- and 1,3,5-Ethynylphenyl Subunits with π-Extended Conjugation. Carbon Dendron Units
  作者：J. Gonzalo Rodríguez、Jorge Esquivias、Antonio Lafuente、Cristina Díaz

  DOI：10.1021/jo034972b

  日期：2003.10.1

  5-ethynylphenyl oligomers were synthesized starting from 3,5-di(trimethylsilylethynyl)phenylacetylene and p-[3,5-di(trimethylsilylethynyl)-1-ethynylphenyl]phenyl acetylene by cross-coupling reaction with a convenient haloaryl derivative, catalyzed by palladium(II)/copper(I), in excellent yield. The terminal acetylenes were efficiently prepared by a specific protection-deprotection methodology. All ethynylphenyl

  从3,5-二（三甲基甲硅烷基乙炔基）苯基乙炔和对-[3,5-二（三甲基甲硅烷基乙炔基）-1-乙炔基苯基]苯基乙炔开始，合成了纳米级共轭的1,4-和1,3,5-乙炔基苯基低聚物。钯（II）/铜（I）催化的方便卤代芳基衍生物交叉偶联反应，收率很高。通过特定的保护-脱保护方法有效地制备了末端乙炔。所获得的所有乙炔基苯基同系物均显示出荧光发射，每个乙炔基苯基单元的红移大约为20 nm，从而增加了共轭链。通过插入1，5-萘亚单元制备平行的共轭乙炔基苯基链，并且该化合物表现出荧光辐射发射。
• Synthesis of nanostructures based on 1,4- and 1,3,5-phenylethynyl units with π-extended conjugation. Carbon networks dendrimer base units
  作者：J.Gonzalo Rodrı́guez、J. Esquivias

  DOI：10.1016/s0040-4039(03)01137-7

  日期：2003.6

  A convenient and efficient synthesis of 3,5-di(silylethynyl)phenylacetylene and p-[3,5-di(silylethynyl)phenylethynyl]phenylacetylene has been carried out. These compounds serve to prepare nanometer-sized conjugated 1,4- and 1,3,5-phenylethynyl oligomers, by means of cross-coupling with a convenient haloaryl derivative, catalysed by palladium(H), in excellent yields. The phenylethynyl homologues show fluorescence emission, the wavelength of which is displaced by approximately 20 nm by each phenylethynyl unit increasing the conjugate chain. (C) 2003 Elsevier Science Ltd. All rights reserved.