11-hydroxyundecyl 2,5-dibromobenzoate | 546109-92-6

• 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: 11-hydroxyundecyl 2,5-dibromobenzoate
• CAS: 546109-92-6
• 化学式: C₁₈H₂₆Br₂O₃
• 分子量: 450.211
• InChiKey: MZOBWWBTSDCMRN-UHFFFAOYSA-N

物化性质

• 沸点：
  477.8±25.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-hydroxyundecyl 2,5-dibromobenzoate 在 palladium dichloride copper(l) iodide 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 11-hydroxyundecyl 2,5-ethynylbenzoate
  参考文献：
  名称：

  Amphiphilic Phenyl−Ethynylene Polymers and Copolymers. Synthesis, Characterization, and Optical Emission Properties

  摘要：

  A series of new rigid amphiphilic aryl-ethynylene homopolymers and copolymers with phenyl, pyridinyl, thionyl, or carbazolyl as aryl units has been synthesized. A single side chain on the phenyl rings (alkyl-hydroxyl ester group) provides an amphiphilic character to the polymer backbone. The polymers are characterized by NMR, elemental analysis and size exclusion chromatography (SEC); the thermal properties are analyzed by TGA, DSC, and X-ray diffraction. The polymers with side chains are enough amphiphilic to give stable Langmuir films on water, and the LB films can be transferred on hydrophilic or hydrophobic substrates. The films are deposited on treated glass or silicon substrate. Analyzed by grazing incidence X-ray analysis (GIXA) and by atomic force microscopy (AFM), they reveal well-structured layering periods of 3.5 and 2.7-2.9 nm for the phenyl homopolymer (pPEnBz) and the copolymers with pyridine (pPEn(Bz-co-Py)) and thiophene (pPEn(Bz-co-Ti)), respectively. These results suggest a rearrangement in a Y-type bilayer for the pPEnBz on a hydrophilic substrate. For copolymers pPEn(Bz-co-Py), and pPEn(Bz-co-Ti), deposited on a hydrophobic substrate, the self-assembly within one layer consists of interdigitated alkyl chains. In solid-state films the polymers and copolymers show a rather good photoluminescence yield and large Stokes-shifts with emission peaks at 539, 502, 569, and 563 nin for pPEnBz, pPEn(Bz-co-Py), pPEn(Bz-co-Ti), and pPEn(Bz-co-Cz), respectively. The photoluminescence quantum yields are decreasing in the series by 23, 15, 12, and 7% respectively, while no emission is observed from pPEnPy. A dichroism on LB films has been found in absorption (R = 2.0, 2.04 and 1.3) and in emission spectra (R = 3.4, 4.0 and 2.6) for pPEnBz, pPEn(Bz-co-Ti) and pPEn(Bz-co-Py), respectively. LED properties are demonstrated using the ITO/polymer/LiF-Al sandwich, yielding photon emission at 555 and 550 nin for pPEnBz and pPEn(Bz-co-Py). These results are very important for the future realization by LB deposition technique of more sophisticated devices for polarized emission with further enhanced brightness and improved light efficiency.

  DOI：

  10.1021/ma020121e
• 作为产物：
  描述：

  11-溴-1-十一醇 、 2,5-二溴苯甲酸 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 以 苯 为溶剂， 以95%的产率得到11-hydroxyundecyl 2,5-dibromobenzoate
  参考文献：
  名称：

  Amphiphilic Phenyl−Ethynylene Polymers and Copolymers. Synthesis, Characterization, and Optical Emission Properties

  摘要：

  A series of new rigid amphiphilic aryl-ethynylene homopolymers and copolymers with phenyl, pyridinyl, thionyl, or carbazolyl as aryl units has been synthesized. A single side chain on the phenyl rings (alkyl-hydroxyl ester group) provides an amphiphilic character to the polymer backbone. The polymers are characterized by NMR, elemental analysis and size exclusion chromatography (SEC); the thermal properties are analyzed by TGA, DSC, and X-ray diffraction. The polymers with side chains are enough amphiphilic to give stable Langmuir films on water, and the LB films can be transferred on hydrophilic or hydrophobic substrates. The films are deposited on treated glass or silicon substrate. Analyzed by grazing incidence X-ray analysis (GIXA) and by atomic force microscopy (AFM), they reveal well-structured layering periods of 3.5 and 2.7-2.9 nm for the phenyl homopolymer (pPEnBz) and the copolymers with pyridine (pPEn(Bz-co-Py)) and thiophene (pPEn(Bz-co-Ti)), respectively. These results suggest a rearrangement in a Y-type bilayer for the pPEnBz on a hydrophilic substrate. For copolymers pPEn(Bz-co-Py), and pPEn(Bz-co-Ti), deposited on a hydrophobic substrate, the self-assembly within one layer consists of interdigitated alkyl chains. In solid-state films the polymers and copolymers show a rather good photoluminescence yield and large Stokes-shifts with emission peaks at 539, 502, 569, and 563 nin for pPEnBz, pPEn(Bz-co-Py), pPEn(Bz-co-Ti), and pPEn(Bz-co-Cz), respectively. The photoluminescence quantum yields are decreasing in the series by 23, 15, 12, and 7% respectively, while no emission is observed from pPEnPy. A dichroism on LB films has been found in absorption (R = 2.0, 2.04 and 1.3) and in emission spectra (R = 3.4, 4.0 and 2.6) for pPEnBz, pPEn(Bz-co-Ti) and pPEn(Bz-co-Py), respectively. LED properties are demonstrated using the ITO/polymer/LiF-Al sandwich, yielding photon emission at 555 and 550 nin for pPEnBz and pPEn(Bz-co-Py). These results are very important for the future realization by LB deposition technique of more sophisticated devices for polarized emission with further enhanced brightness and improved light efficiency.

  DOI：

  10.1021/ma020121e