10-(5-bromothiophen-2-yl)-9H-pyreno[4,5-d]imidazole | 1300113-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 10-(5-bromothiophen-2-yl)-9H-pyreno[4,5-d]imidazole
• CAS: 1300113-86-3
• 化学式: C₂₁H₁₁BrN₂S
• 分子量: 403.302
• InChiKey: XTOYSLMSSRMQTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.68
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  10-(5-bromothiophen-2-yl)-9H-pyreno[4,5-d]imidazole 在 四(三苯基膦)钯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.5h， 生成 5-Dodecyl-4-[5-[5-[5-(5-dodecyl-3,5-diazapentacyclo[9.6.2.02,6.07,19.014,18]nonadeca-1(17),2(6),3,7,9,11(19),12,14(18),15-nonaen-4-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-3,5-diazapentacyclo[9.6.2.02,6.07,19.014,18]nonadeca-1(17),2(6),3,7,9,11(19),12,14(18),15-nonaene
  参考文献：
  名称：

  Symmetrical fluorescent oligothiophene and benzene centered bispyrenoimidazole derivatives with double n-dodecyl chains showing high thermal stability

  摘要：

  A family of symmetrical oligothiophene (dithiophene, terthiophene, and quaterthiophene) or benzene centered bispyrenoimidazole derivatives, having the same coplanar pyrenoimidazole terminal groups at each side, has been synthesized via Radziszewski, N-alkylation, and the following Pd(PPh3)(4) catalyzed Suzuki and Stille coupling reactions. Double n-dodecyl chains are introduced to the molecules at the same time in order to increase their solubility in organic solvents. UV-vis and fluorescence spectra as well as thermal properties have been studied. The results demonstrate that compound 4 with a benzene linker displays the strongest fluorescence intensity, and oligothiophene centered bispyrenoimidazole derivatives 5-7 show obvious bathochromic shifts compared with benzene centered compound 4. It is worth mentioning that this family of compounds exhibits excellent thermal stability with the decomposition temperature higher than 400 degrees C even if the incorporation of double n-dodecyl chains. Furthermore, X-ray single-crystal structures of one representative compound 4 center dot(CHCl3)(2) and an intermediate 3 have been described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.003
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 芘-4,5-二酮 在 ammonium acetate 、 溶剂黄146 作用下， 反应 24.0h， 以66%的产率得到10-(5-bromothiophen-2-yl)-9H-pyreno[4,5-d]imidazole
  参考文献：
  名称：

  Novel Pyrenoimidazole-Based Organic Dyes for Dye-Sensitized Solar Cells

  摘要：

  A novel class of organic dyes containing pyrenoimidazole donors, cyanoacryllc acid acceptors, and ollgothiophene pi-linkers has been synthesized and characterized. The electro-optical properties of these dyes can be tuned by changing the conjugation length of the pi-linkers. A dye containing terthiophene in the conjugation pathway exhibited a solar energy-to-electricity conversion efficiency of 5.65%.

  DOI：

  10.1021/ol2006874