2-[12-(2,3,5,6-tetrafluorophenyl)dodecyloxy]-tetrahydro-2H-pyran | 1227664-39-2

• 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: 2-[12-(2,3,5,6-tetrafluorophenyl)dodecyloxy]-tetrahydro-2H-pyran
• CAS: 1227664-39-2
• 化学式: C₂₃H₃₄F₄O₂
• 分子量: 418.515
• InChiKey: XNDTVPQYAIHLRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  29.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  5''-bromo-5-hexyl-3''-methyl-2,2':5'2''-terthiophene 、 2-[12-(2,3,5,6-tetrafluorophenyl)dodecyloxy]-tetrahydro-2H-pyran 在 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 C₄₂H₅₄F₄O₂S₃
  参考文献：
  名称：

  Nanostructured Liquid Crystals Combining Ionic and Electronic Functions

  摘要：

  New molecular materials combining ionic and electronic functions have been prepared by using liquid crystals consisting of terthiophene-based mesogens and terminal imidazolium groups. These liquid crystals show thermotropic smectic A phases. Nanosegregation of the pi-conjugated mesogens and the ionic imidazolium moieties leads to the formation of layered liquid-crystalline (LC) structures consisting of 2D alternating pathways for electronic charges and ionic species. These nanostructured materials act as efficient electrochromic redox systems that exhibit coupled electrochemical reduction and oxidation in the ordered bulk states. For example, compound 1 having the terthienylphenylcyanoethylene mesogen and the imidazolium triflate moiety forms the smectic LC nanostructure. Distinct reversible electrochromic responses are observed for compound 1 without additional electrolyte solution on the application of double-potential steps between 0 and 2.5 V in the smectic A phase at 160 degrees C. In contrast, compound 2 having a tetrafluorophenylterthiophene moiety and compound 3 having a phenylterthiophene moiety exhibit irreversible cathodic reduction and reversible anodic oxidation in the smectic A phases. The use of poly(3,4-ethylenedioxythiophene)-poly(4-styrene sulfonate) (PEDOT-PSS) as an electron-accepting layer on the cathode leads to the distinct electrochromic responses for 2 and 3. These results show that new self-organized molecular redox systems can be built by nanosegregated pi-conjugated liquid crystals containing imidazolium moieties with and without electroactive thin layers on the electrodes.

  DOI：

  10.1021/ja101366x
• 作为产物：
  描述：

  1,2,4,5-四氟苯 、 2-[(12-bromododecyl)oxy]tetrahydro-2H-pyran 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以86%的产率得到2-[12-(2,3,5,6-tetrafluorophenyl)dodecyloxy]-tetrahydro-2H-pyran
  参考文献：
  名称：

  Nanostructured Liquid Crystals Combining Ionic and Electronic Functions

  摘要：

  New molecular materials combining ionic and electronic functions have been prepared by using liquid crystals consisting of terthiophene-based mesogens and terminal imidazolium groups. These liquid crystals show thermotropic smectic A phases. Nanosegregation of the pi-conjugated mesogens and the ionic imidazolium moieties leads to the formation of layered liquid-crystalline (LC) structures consisting of 2D alternating pathways for electronic charges and ionic species. These nanostructured materials act as efficient electrochromic redox systems that exhibit coupled electrochemical reduction and oxidation in the ordered bulk states. For example, compound 1 having the terthienylphenylcyanoethylene mesogen and the imidazolium triflate moiety forms the smectic LC nanostructure. Distinct reversible electrochromic responses are observed for compound 1 without additional electrolyte solution on the application of double-potential steps between 0 and 2.5 V in the smectic A phase at 160 degrees C. In contrast, compound 2 having a tetrafluorophenylterthiophene moiety and compound 3 having a phenylterthiophene moiety exhibit irreversible cathodic reduction and reversible anodic oxidation in the smectic A phases. The use of poly(3,4-ethylenedioxythiophene)-poly(4-styrene sulfonate) (PEDOT-PSS) as an electron-accepting layer on the cathode leads to the distinct electrochromic responses for 2 and 3. These results show that new self-organized molecular redox systems can be built by nanosegregated pi-conjugated liquid crystals containing imidazolium moieties with and without electroactive thin layers on the electrodes.

  DOI：

  10.1021/ja101366x