N-(4-ethynylphenyl)-3,4,5-tris(hexadecyloxy)benzamide | 1201810-32-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-ethynylphenyl)-3,4,5-tris(hexadecyloxy)benzamide
• 英文别名: N-(4-ethynylphenyl)-3,4,5-trihexadecoxybenzamide
• CAS: 1201810-32-3
• 化学式: C₆₃H₁₀₇NO₄
• 分子量: 942.547
• InChiKey: OFOKTJNRZXJTJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.2
• 重原子数：
  68
• 可旋转键数：
  51
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-二溴芘 、 N-(4-ethynylphenyl)-3,4,5-tris(hexadecyloxy)benzamide 在 正丙胺 、 四(三苯基膦)钯 作用下， 以74%的产率得到3,4,5-trihexadecoxy-N-[4-[2-[6-[2-[4-[(3,4,5-trihexadecoxybenzoyl)amino]phenyl]ethynyl]pyren-1-yl]ethynyl]phenyl]benzamide
  参考文献：
  名称：

  Luminescent Ethynyl−Pyrene Liquid Crystals and Gels for Optoelectronic Devices

  摘要：

  Two functional ethynyl-pyrene derivatives have been designed and synthesized by di- and tetra-substitutions of bromo pyrene derivatives with N-(4-ethynylphenyl)-3,4,5-tris(hexadecyloxy)benzamide fragments. The photoluminescence wavelength of the pyrene core can be tuned by the substitution pattern and the state of matter (solid, solution, gel, or liquid crystal). The disubstituted pyrene derivative 1 is not mesomorphic but produces robust and highly fluorescent gels in DMF, toluene, and cyclohexane. The well-defined fibers and ropes of the gel states were characterized by SEM and laser scanning confocal microscopy, and extended over several micrometers. The gels were integrated as active layers in field-effect transistors, which provided good bulk electron and hole charge mobilities as well as light emission generation. The tetra-substituted pyrene derivative is not a gelator but displays a stable liquid crystalline phase with 2D hexagonal symmetry between 20 and 200 degrees C. The pronounced luminescence properties of the mesophase allow one to observe original mesophase textures with flower-like patterns directly by fluorescence microscopy without crossed-polarizers.

  DOI：

  10.1021/ja908061q
• 作为产物：
  描述：

  3,4,5-tris(hexadecyloxy)-N-(4-((trimethylsilyl)ethynyl)phenyl)benzamide 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 以95%的产率得到N-(4-ethynylphenyl)-3,4,5-tris(hexadecyloxy)benzamide
  参考文献：
  名称：

  Luminescent Ethynyl−Pyrene Liquid Crystals and Gels for Optoelectronic Devices

  摘要：

  Two functional ethynyl-pyrene derivatives have been designed and synthesized by di- and tetra-substitutions of bromo pyrene derivatives with N-(4-ethynylphenyl)-3,4,5-tris(hexadecyloxy)benzamide fragments. The photoluminescence wavelength of the pyrene core can be tuned by the substitution pattern and the state of matter (solid, solution, gel, or liquid crystal). The disubstituted pyrene derivative 1 is not mesomorphic but produces robust and highly fluorescent gels in DMF, toluene, and cyclohexane. The well-defined fibers and ropes of the gel states were characterized by SEM and laser scanning confocal microscopy, and extended over several micrometers. The gels were integrated as active layers in field-effect transistors, which provided good bulk electron and hole charge mobilities as well as light emission generation. The tetra-substituted pyrene derivative is not a gelator but displays a stable liquid crystalline phase with 2D hexagonal symmetry between 20 and 200 degrees C. The pronounced luminescence properties of the mesophase allow one to observe original mesophase textures with flower-like patterns directly by fluorescence microscopy without crossed-polarizers.

  DOI：

  10.1021/ja908061q

文献信息

• Luminescence modulation in liquid crystalline phases containing a dispiro[fluorene-9,11′-indeno[1,2-b]fluorene-12′,9′′-fluorene] core
  作者：Sébastien Thiery、Benoît Heinrich、Bertrand Donnio、Cyril Poriel、Franck Camerel

  DOI：10.1039/c4tc00038b

  日期：——

  Luminescence modulations of a bulky dispiro[fluorene-9,11′-indeno[1,2-b]fluorene-12′,9′′-fluorene] (DSF-IF) core embedded in thermotropic liquid crystal phases.

  一个大的二螺旋[芴-9,11′-吲哚[1,2-b]芴-12′,9′′-芴]（DSF-IF）核心嵌入热致液晶相中的发光调制。
• Luminescent Ethynyl−Pyrene Liquid Crystals and Gels for Optoelectronic Devices
  作者：Stéphane Diring、Franck Camerel、Bertrand Donnio、Thierry Dintzer、Stefano Toffanin、Raffaella Capelli、Michele Muccini、Raymond Ziessel

  DOI：10.1021/ja908061q

  日期：2009.12.23

  Two functional ethynyl-pyrene derivatives have been designed and synthesized by di- and tetra-substitutions of bromo pyrene derivatives with N-(4-ethynylphenyl)-3,4,5-tris(hexadecyloxy)benzamide fragments. The photoluminescence wavelength of the pyrene core can be tuned by the substitution pattern and the state of matter (solid, solution, gel, or liquid crystal). The disubstituted pyrene derivative 1 is not mesomorphic but produces robust and highly fluorescent gels in DMF, toluene, and cyclohexane. The well-defined fibers and ropes of the gel states were characterized by SEM and laser scanning confocal microscopy, and extended over several micrometers. The gels were integrated as active layers in field-effect transistors, which provided good bulk electron and hole charge mobilities as well as light emission generation. The tetra-substituted pyrene derivative is not a gelator but displays a stable liquid crystalline phase with 2D hexagonal symmetry between 20 and 200 degrees C. The pronounced luminescence properties of the mesophase allow one to observe original mesophase textures with flower-like patterns directly by fluorescence microscopy without crossed-polarizers.