2,5-bis[(4-dodecyloxyphenyl)hydroxymethyl]thiophene | 1401254-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-bis[(4-dodecyloxyphenyl)hydroxymethyl]thiophene
• 英文别名: (4-Dodecoxyphenyl)-[5-[(4-dodecoxyphenyl)-hydroxymethyl]thiophen-2-yl]methanol；(4-dodecoxyphenyl)-[5-[(4-dodecoxyphenyl)-hydroxymethyl]thiophen-2-yl]methanol
• CAS: 1401254-85-0
• 化学式: C₄₂H₆₄O₄S
• 分子量: 665.034
• InChiKey: IYFJSUHNMHKQRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  47
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  87.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  吡咯 、 2,5-bis[(4-dodecyloxyphenyl)hydroxymethyl]thiophene 在 三氟化硼乙醚 作用下， 反应 1.0h， 以93%的产率得到2-[(4-dodecoxyphenyl)-[5-[(4-dodecoxyphenyl)-(1H-pyrrol-2-yl)methyl]thiophen-2-yl]methyl]-1H-pyrrole
  参考文献：
  名称：

  Synthesis and Optical and Electronic Properties of Core-Modified 21,23-Dithiaporphyrins

  摘要：

  Core-modified 21,23-dithiaporphyrins, meso-substituted with both electron-withdrawing 4-phenylcarboxylic acids and related butyl esters, and electron-donating phenyl-dodecyl ethers were synthesized. The porphyrins displayed broad absorbance profiles that spanned from 400 to 800 nm with molar absorptivities ranging from 2500 to 200000 M-1 cm(-1). Electrochemical experiments showed the dithiaporphyrins undergo two consecutive, one-electron, quasi-reversible oxidations and reductions at -1.78, -1.43, 0.63, and 0.91 V versus a ferrocene/ferrocenium internal standard. Spectroelectrochemistry and cyclic voltammetry revealed the dithiaporphyrins are stable and can endure many cycles of oxidation and reduction without signs of decomposition. The electronics of the two dithiaporphyrins were similar, and DFT calculations showed the HOMO-LUMO energy difference was smaller than tetrapyrrolic porphyrin analogues. Overall, the combination of desirable electronics, namely: quasi-reversible oxidations and reductions as well as broad absorbance profiles, combined with stability, imply that these core-modified 21,23-dithiaporphyirns could be potentially used as an ambipolar material for organic electronic applications.

  DOI：

  10.1021/jo302707f
• 作为产物：
  描述：

  溴代十二烷 在 正丁基锂 、 四甲基乙二胺 、 potassium carbonate 、 potassium iodide 作用下， 以 正己烷 、 丙酮 为溶剂， 反应 27.0h， 生成 2,5-bis[(4-dodecyloxyphenyl)hydroxymethyl]thiophene
  参考文献：
  名称：

  Synthesis and Optical and Electronic Properties of Core-Modified 21,23-Dithiaporphyrins

  摘要：

  Core-modified 21,23-dithiaporphyrins, meso-substituted with both electron-withdrawing 4-phenylcarboxylic acids and related butyl esters, and electron-donating phenyl-dodecyl ethers were synthesized. The porphyrins displayed broad absorbance profiles that spanned from 400 to 800 nm with molar absorptivities ranging from 2500 to 200000 M-1 cm(-1). Electrochemical experiments showed the dithiaporphyrins undergo two consecutive, one-electron, quasi-reversible oxidations and reductions at -1.78, -1.43, 0.63, and 0.91 V versus a ferrocene/ferrocenium internal standard. Spectroelectrochemistry and cyclic voltammetry revealed the dithiaporphyrins are stable and can endure many cycles of oxidation and reduction without signs of decomposition. The electronics of the two dithiaporphyrins were similar, and DFT calculations showed the HOMO-LUMO energy difference was smaller than tetrapyrrolic porphyrin analogues. Overall, the combination of desirable electronics, namely: quasi-reversible oxidations and reductions as well as broad absorbance profiles, combined with stability, imply that these core-modified 21,23-dithiaporphyirns could be potentially used as an ambipolar material for organic electronic applications.

  DOI：

  10.1021/jo302707f