1,2-dimethyl-3-(12-(2,3,5,6-tetrafluoro-4-(5''-hexyl-3-methyl-[2,2':5',2''-terthiophen]-5-yl)phenyl)dodecyl)-1H-imidazol-3-ium bromide | 1227664-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 1,2-dimethyl-3-(12-(2,3,5,6-tetrafluoro-4-(5''-hexyl-3-methyl-[2,2':5',2''-terthiophen]-5-yl)phenyl)dodecyl)-1H-imidazol-3-ium bromide
• CAS: 1227664-41-6
• 化学式: Br*C₄₂H₅₃F₄N₂S₃
• 分子量: 837.992
• InChiKey: ULQPMFCYLIJJOC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  10.94
• 重原子数：
  52.0
• 可旋转键数：
  21.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,2-dimethyl-3-(12-(2,3,5,6-tetrafluoro-4-(5''-hexyl-3-methyl-[2,2':5',2''-terthiophen]-5-yl)phenyl)dodecyl)-1H-imidazol-3-ium bromide 、 silver trifluoromethanesulfonate 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到
  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：

  1,2-二甲基咪唑 、 5-(4-(12-bromododecyl)-2,3,5,6-tetrafluorophenyl)-5''-hexyl-3-methyl-2,2':5',2''-terthiophene 以 甲苯 为溶剂， 反应 12.0h， 以45%的产率得到1,2-dimethyl-3-(12-(2,3,5,6-tetrafluoro-4-(5''-hexyl-3-methyl-[2,2':5',2''-terthiophen]-5-yl)phenyl)dodecyl)-1H-imidazol-3-ium bromide
  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