4,7-dibromo-2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-1H-benzo[d]imidazole | 1259532-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4,7-dibromo-2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-1H-benzo[d]imidazole
• CAS: 1259532-61-0
• 化学式: C₁₃H₈Br₂N₂O₂S
• 分子量: 416.093
• InChiKey: HDSBQVRPSAVQFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  47.14
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,7-dibromo-2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-1H-benzo[d]imidazole 、 三丁基(2,3-二氢噻吩并[3,4-b]-[1,4]二恶英-5-基)锡烷 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以60.3%的产率得到2,4-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-7-(2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Donor–acceptor–donor type conjugated polymers for electrochromic applications: benzimidazole as the acceptor unit

  摘要：

  Donor-acceptor-donor (DAD) type benzimidazole (Blm) and 3,4 ethylenedioxythiophene (EDOT) bearing monomers were synthesized and electrochemically polymerized. Pendant group at 2-C position of the imidazole ring was functionalized with phenyl (P1), EDOT (P2) and ferrocene (P3) in order to observe substituent effect on electrochemical and electrochromic properties of corresponding polymers. Spectroelectrochemical results showed that different pendant groups resulted in polymers with slightly different optical band gaps (1.75, 1.69 and 1.77 eV respectively) and different number of achievable colored states. Optoelectronic performance and comparison of results with other well known pi-accepting benzazole bearing DAD type polymers were reported in detail. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2010.10.045
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 4,7-dibromo-2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Donor–acceptor–donor type conjugated polymers for electrochromic applications: benzimidazole as the acceptor unit

  摘要：

  Donor-acceptor-donor (DAD) type benzimidazole (Blm) and 3,4 ethylenedioxythiophene (EDOT) bearing monomers were synthesized and electrochemically polymerized. Pendant group at 2-C position of the imidazole ring was functionalized with phenyl (P1), EDOT (P2) and ferrocene (P3) in order to observe substituent effect on electrochemical and electrochromic properties of corresponding polymers. Spectroelectrochemical results showed that different pendant groups resulted in polymers with slightly different optical band gaps (1.75, 1.69 and 1.77 eV respectively) and different number of achievable colored states. Optoelectronic performance and comparison of results with other well known pi-accepting benzazole bearing DAD type polymers were reported in detail. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2010.10.045