1,4-bis(bromomethyl)-2,5-bis(undecyloxy)benzene | 1379868-69-5

• 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: 1,4-bis(bromomethyl)-2,5-bis(undecyloxy)benzene
• CAS: 1379868-69-5
• 化学式: C₃₀H₅₂Br₂O₂
• 分子量: 604.55
• InChiKey: GWJFDDZPGVQQOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  34.0
• 可旋转键数：
  24.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,4-bis(bromomethyl)-2,5-bis(undecyloxy)benzene 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 1,4-di(undecoxy)-2,5-bis[(E)-2-(4-undecoxyphenyl)ethenyl]benzene
  参考文献：
  名称：

  C ？π共轭低聚物中的H /π相互作用指导的自组装

  摘要：

  我们报告了基于低聚亚苯基亚乙烯基（OPV）的π共轭骨架中CH /π氢键驱动的自组装，并通过使用单晶结构在分子水平上追踪了相互作用的起源。OPV的设计在芳族核中带有适当的侧基，并沿分子轴的碳氢化合物或碳氟化合物尾部变化。研究了芳香族π堆积，范德华力，疏水效应和CH /π相互作用对OPV分子的热致液晶性的影响。烃类OPV的单晶结构为π环（氢键受体）和烷基CH（氢键供体）之间存在CH /π相互作用提供了直接证据。四个重要的晶体学参数d c-x = 3.79Å，θ= 21.49°，φ = 150.25°，d Hp-x = 0.73Å，根据典型的CH /π相互作用进行匹配。CH /π相互作用促进了x - y平面中液晶元的紧密堆积，并进一步沿c方向突出轴产生层状结构。在没有CH /π相互作用的情况下，范德华相互作用使装配趋向于Schlieren向列织构。碳氟化合物OPV表现出近晶液晶结构，进一步经历了Smectic

  DOI：

  10.1002/chem.201102670
• 作为产物：
  描述：

  1-溴十一烷 在 氢溴酸 、 溶剂黄146 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 56.0h， 生成 1,4-bis(bromomethyl)-2,5-bis(undecyloxy)benzene
  参考文献：
  名称：

  C ？π共轭低聚物中的H /π相互作用指导的自组装

  摘要：

  我们报告了基于低聚亚苯基亚乙烯基（OPV）的π共轭骨架中CH /π氢键驱动的自组装，并通过使用单晶结构在分子水平上追踪了相互作用的起源。OPV的设计在芳族核中带有适当的侧基，并沿分子轴的碳氢化合物或碳氟化合物尾部变化。研究了芳香族π堆积，范德华力，疏水效应和CH /π相互作用对OPV分子的热致液晶性的影响。烃类OPV的单晶结构为π环（氢键受体）和烷基CH（氢键供体）之间存在CH /π相互作用提供了直接证据。四个重要的晶体学参数d c-x = 3.79Å，θ= 21.49°，φ = 150.25°，d Hp-x = 0.73Å，根据典型的CH /π相互作用进行匹配。CH /π相互作用促进了x - y平面中液晶元的紧密堆积，并进一步沿c方向突出轴产生层状结构。在没有CH /π相互作用的情况下，范德华相互作用使装配趋向于Schlieren向列织构。碳氟化合物OPV表现出近晶液晶结构，进一步经历了Smectic

  DOI：

  10.1002/chem.201102670

文献信息

• Direct Evidence for Secondary Interactions in Planar and Nonplanar Aromatic π-Conjugates and Their Photophysical Characteristics in Solid-State Assemblies
  作者：Mahima Goel、Karnati Narasimha、Manickam Jayakannan

  DOI：10.1021/acs.jpcb.5b01956

  日期：2015.4.16

  Direct evidence for non-covalent secondary interactions in planar and nonplanar aromatic pi-conjugates and their solid-state assemblies is established. A series of horizontally, vertically, and radially expanded oligo(phenylenevinylene)s (H-OPVs, V-OPVs, and R-OPVs, respectively) were designed with a fixed pi-core and variable alkyl chain lengths on the periphery. Single-crystal structures of the OPVs were resolved to trace the secondary interactions that direct the solid-state self-organization and molecular packing of the chromophores. The H-OPVs were found to be planar, and they did not show any secondary interactions in the crystal lattices. The V-OPVs and R-OPVs were found to be nonplanar and to exhibit multiple CH/pi hydrogen-bonding interactions among aryl hydrogen donors and acceptors. The enthalpies of the melting and crystallization transitions revealed that the planar H-OPVs are highly crystalline compared with the nonplanar R-OPVs and V-OPVs. Polarized light microscopy studies revealed the formation of one-dimensional nematic mesophases in H-OPVs. The absolute solid-state photoluminescence quantum yields (PLQYs) of the OPVs were determined using an integrating sphere setup. The highly packed H-OPVs showed low PLQYs compared with those of the weakly packed V-OPVs and R-OPVs. Time-resolved fluorescence decay measurements revealed that the excited-state decay dynamics of highly packed H-OPVs was much faster with respect to their low PLQYs. The decay profiles were found to be relatively slow (with higher life time (tau)) in the V-OPVs and R-OPVs. A field-effect transistor (FET) device was constructed for an OPV sample that showed a hole carrier mobility in the range of 10(-5) cm(2) V-1 s(-1). The present investigation thus provides a new opportunity to trace the role of secondary interactions on pi-conjugated mesophase self-assemblies and their solid-state emission and FET devices, more specifically based on OPV chromophores.