4-bromo-2-(1H,1H,2H,2H,3H,3H-perfluoroisodecyl)phenol | 610778-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-bromo-2-(1H,1H,2H,2H,3H,3H-perfluoroisodecyl)phenol
• 英文别名: 4-Bromo-2-[4,4,5,5,6,6,7,7,8,9,9,9-dodecafluoro-8-(trifluoromethyl)nonyl]phenol；4-bromo-2-[4,4,5,5,6,6,7,7,8,9,9,9-dodecafluoro-8-(trifluoromethyl)nonyl]phenol
• CAS: 610778-18-2
• 化学式: C₁₆H₁₀BrF₁₅O
• 分子量: 583.135
• InChiKey: PIDMBACJRPFEPM-UHFFFAOYSA-N

物化性质

• 沸点：
  335.1±42.0 °C(Predicted)
• 密度：
  1.661±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(1H,1H,2H,2H,3H,3H-perfluoroisodecyl)phenol 在 四(三苯基膦)钯 、 乙二醇二甲醚 、 三溴化硼 、 碳酸氢钠 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 34.0h， 生成 4,4'-diallyloxy-3,3'-bis(1H,1H,2H,2H,3H,3H-perfluoroisodecyl)biphenyl
  参考文献：
  名称：

  具有（半）全氟侧链的棒状双亲分子：具有新液晶相结构的多亲嵌段分子

  摘要：

  作为关键步骤，通过钯催化的交叉偶联反应合成了由刚性联苯单元、两个末端极性 1,2-二醇单元和侧向连接（半）全氟化链组成的新型双亲分子。通过偏光光学显微镜、DSC和X射线散射研究了这些化合物的热致液晶行为，并研究了侧链的长度、数量、结构和位置对介晶性质的影响。在侧向半全氟化链伸长时发现了多种独特的液晶相。对于短链和中链长度，观察到一系列柱状相，并且随着侧链的进一步伸长，发现了一系列具有层状结构的新型中间相。在柱状相中，非极性侧链分离成柱状，这些柱状体嵌入由联苯单元组成的蜂窝状圆柱体网络中。二醇基团的氢键网络串提供保持整体结构的内聚力。改变侧链的长度会影响柱的直径，从而决定包围这些柱所需的联苯单元的数量。这些单位的数量 [4 (c2mm, p4mm)、5 (p2gg)、6 (p6mm)、8 (c2mm) 或 10 (p2gg)] 定义了圆柱体的形状以及柱状相的晶格类型。有人提出，具有 p2gg

  DOI：

  10.1021/ja036213g
• 作为产物：
  描述：

  2-烯丙基酚 在 四(三苯基膦)钯 、 氢溴酸 、 溶剂黄146 、 二甲基亚砜 作用下， 以 正己烷 为溶剂， 生成 4-bromo-2-(1H,1H,2H,2H,3H,3H-perfluoroisodecyl)phenol
  参考文献：
  名称：

  Liquid Crystalline Bolaamphiphiles with Semiperfluorinated Lateral Chains:  Competition between Layerlike and Honeycomb-Like Organization

  摘要：

  Novel bolaamphiphilic triblockmolecules consisting of a rigid biphenyl unit, with a polar 2,3-dihydroxypropyloxy group and a phenolic OH group at opposite ends, as well as a semiperfluorinated chain in a lateral position have been synthesized via palladium catalyzed cross coupling reactions as the key steps. The thermotropic liquid crystalline behavior of these compounds was investigated by polarized light microscopy, DSC and X-ray scattering, and the influence of the length of the lateral chain on the mesomorphic properties was studied. The compound with the shortest chain as well as the long chain derivatives form lamellar mesophases composed of segregated layers of the bolaamphiphilic moieties and sublayers comprising the fluid lateral chains. The layers within the lamellar phases of the short chain compound adopt a positional correlation, leading to a 2D lattice (Col(r)/p2mm), whereas the layers of the lamellar phases of the long chain derivatives are noncorrelated (Lam). Compounds with a medium chain length organize into columnar phases, where the nonpolar lateral chains segregate into columns, which are embedded in networks of regular (Col(h)) or stretched (Col(r)/c2mm) hexagonal cylinder shells consisting of the bolaamphiphilic units. In total, an unusual phase sequence was found, where, with respect to the chain length, columnar mesophases occur between two mesophases with layer organization.

  DOI：

  10.1021/ja048224v

文献信息

• Calamitic Bolaamphiphiles with (Semi)Perfluorinated Lateral Chains:  Polyphilic Block Molecules with New Liquid Crystalline Phase Structures
  作者：Xiaohong Cheng、Marko Prehm、Malay Kumar Das、Jens Kain、Ute Baumeister、Siegmar Diele、Dag Leine、Alfred Blume、Carsten Tschierske

  DOI：10.1021/ja036213g

  日期：2003.9.1

  were studied. A wide variety of unique liquid crystalline phases were found upon elongation of the lateral semiperfluorinated chains. For short- and medium-chain length a series of columnar phases were observed, and upon further elongation of the lateral chain a series of novel mesophases with layer structures were found. In the columnar phases, the nonpolar lateral chains segregate into columns, which

  作为关键步骤，通过钯催化的交叉偶联反应合成了由刚性联苯单元、两个末端极性 1,2-二醇单元和侧向连接（半）全氟化链组成的新型双亲分子。通过偏光光学显微镜、DSC和X射线散射研究了这些化合物的热致液晶行为，并研究了侧链的长度、数量、结构和位置对介晶性质的影响。在侧向半全氟化链伸长时发现了多种独特的液晶相。对于短链和中链长度，观察到一系列柱状相，并且随着侧链的进一步伸长，发现了一系列具有层状结构的新型中间相。在柱状相中，非极性侧链分离成柱状，这些柱状体嵌入由联苯单元组成的蜂窝状圆柱体网络中。二醇基团的氢键网络串提供保持整体结构的内聚力。改变侧链的长度会影响柱的直径，从而决定包围这些柱所需的联苯单元的数量。这些单位的数量 [4 (c2mm, p4mm)、5 (p2gg)、6 (p6mm)、8 (c2mm) 或 10 (p2gg)] 定义了圆柱体的形状以及柱状相的晶格类型。有人提出，具有 p2gg
• Liquid Crystalline Bolaamphiphiles with Semiperfluorinated Lateral Chains:  Competition between Layerlike and Honeycomb-Like Organization
  作者：Xiaohong Cheng、Malay Kumar Das、Ute Baumeister、Siegmar Diele、Carsten Tschierske

  DOI：10.1021/ja048224v

  日期：2004.10.1

  Novel bolaamphiphilic triblockmolecules consisting of a rigid biphenyl unit, with a polar 2,3-dihydroxypropyloxy group and a phenolic OH group at opposite ends, as well as a semiperfluorinated chain in a lateral position have been synthesized via palladium catalyzed cross coupling reactions as the key steps. The thermotropic liquid crystalline behavior of these compounds was investigated by polarized light microscopy, DSC and X-ray scattering, and the influence of the length of the lateral chain on the mesomorphic properties was studied. The compound with the shortest chain as well as the long chain derivatives form lamellar mesophases composed of segregated layers of the bolaamphiphilic moieties and sublayers comprising the fluid lateral chains. The layers within the lamellar phases of the short chain compound adopt a positional correlation, leading to a 2D lattice (Col(r)/p2mm), whereas the layers of the lamellar phases of the long chain derivatives are noncorrelated (Lam). Compounds with a medium chain length organize into columnar phases, where the nonpolar lateral chains segregate into columns, which are embedded in networks of regular (Col(h)) or stretched (Col(r)/c2mm) hexagonal cylinder shells consisting of the bolaamphiphilic units. In total, an unusual phase sequence was found, where, with respect to the chain length, columnar mesophases occur between two mesophases with layer organization.