5-dodecyl-2-(triethoxymethyl)thiophene | 1443982-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-dodecyl-2-(triethoxymethyl)thiophene
• 英文别名: 2-Dodecyl-5-(triethoxymethyl)thiophene；2-dodecyl-5-(triethoxymethyl)thiophene
• CAS: 1443982-43-1
• 化学式: C₂₃H₄₂O₃S
• 分子量: 398.651
• InChiKey: NTFLGOGVWXYBJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-dodecyl-2-(triethoxymethyl)thiophene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四丁基溴化铵 、 potassium carbonate 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 水 、 甲苯 为溶剂， 反应 39.0h， 生成 4,8-bis(4-dodecylphenyl)-2,6-bis(5-dodecylthien-2-yl)benzo[1,2-d;4,5-d′]bis(oxazole)
  参考文献：
  名称：

  Influence of Conjugation Axis on the Optical and Electronic Properties of Aryl-Substituted Benzobisoxazoles

  摘要：

  Six different 2,6-diethyl-4,8-diarylbenzo[1,2-d:4,5-d']bis(oxazoles) and four different 2,4,6,8-tetraarylbenzobisoxazoles were synthesized in two steps: a Lewis acid catalyzed orthoester cyclization followed by a Suzuki or Stille cross-coupling with various arenes. The influence of aryl group substitution and/or conjugation axis variation on the optical and electronic properties of these benzobis(oxazole) (BBO) compounds was evaluated Structural modifications could be used to alter the HOMO, LUMO, and band gap over a range of 1.0, 0.5, and 0.5 eV, respectively. However, depending on the location and identity of the substituent, the HOMO level Can be altered without significantly impacting the LUMO level. This is supported by the calculated frontier molecular orbitals. Our results indicate that the FMOs and band gaps of benzobisoxazoles can be readily modified either jointly or individually.

  DOI：

  10.1021/jo4007927
• 作为产物：
  描述：

  原碳酸四乙酯 、 2-溴-5-十二烷基噻吩 在 异丙基氯化镁 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以51%的产率得到5-dodecyl-2-(triethoxymethyl)thiophene
  参考文献：
  名称：

  Influence of Conjugation Axis on the Optical and Electronic Properties of Aryl-Substituted Benzobisoxazoles

  摘要：

  Six different 2,6-diethyl-4,8-diarylbenzo[1,2-d:4,5-d']bis(oxazoles) and four different 2,4,6,8-tetraarylbenzobisoxazoles were synthesized in two steps: a Lewis acid catalyzed orthoester cyclization followed by a Suzuki or Stille cross-coupling with various arenes. The influence of aryl group substitution and/or conjugation axis variation on the optical and electronic properties of these benzobis(oxazole) (BBO) compounds was evaluated Structural modifications could be used to alter the HOMO, LUMO, and band gap over a range of 1.0, 0.5, and 0.5 eV, respectively. However, depending on the location and identity of the substituent, the HOMO level Can be altered without significantly impacting the LUMO level. This is supported by the calculated frontier molecular orbitals. Our results indicate that the FMOs and band gaps of benzobisoxazoles can be readily modified either jointly or individually.

  DOI：

  10.1021/jo4007927

文献信息

• Influence of Conjugation Axis on the Optical and Electronic Properties of Aryl-Substituted Benzobisoxazoles
  作者：Brian C. Tlach、Aimée L. Tomlinson、Alden G. Ryno、Dawn D. Knoble、Dana L. Drochner、Kyle J. Krager、Malika Jeffries-EL

  DOI：10.1021/jo4007927

  日期：2013.7.5

  Six different 2,6-diethyl-4,8-diarylbenzo[1,2-d:4,5-d']bis(oxazoles) and four different 2,4,6,8-tetraarylbenzobisoxazoles were synthesized in two steps: a Lewis acid catalyzed orthoester cyclization followed by a Suzuki or Stille cross-coupling with various arenes. The influence of aryl group substitution and/or conjugation axis variation on the optical and electronic properties of these benzobis(oxazole) (BBO) compounds was evaluated Structural modifications could be used to alter the HOMO, LUMO, and band gap over a range of 1.0, 0.5, and 0.5 eV, respectively. However, depending on the location and identity of the substituent, the HOMO level Can be altered without significantly impacting the LUMO level. This is supported by the calculated frontier molecular orbitals. Our results indicate that the FMOs and band gaps of benzobisoxazoles can be readily modified either jointly or individually.