3',4''-dioctyl-2,2':5',2'':5'',2'''-tetrathienyl | 655241-79-5

• 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: 3',4''-dioctyl-2,2':5',2'':5'',2'''-tetrathienyl
• 英文别名: 3',4''-dioctyl-2,2':5',2'':5'',2'''-quaterthiophene；3-Octyl-5-(4-octyl-5-thiophen-2-ylthiophen-2-yl)-2-thiophen-2-ylthiophene
• CAS: 655241-79-5
• 化学式: C₃₂H₄₂S₄
• 分子量: 554.949
• InChiKey: FSTWNKKRSRGHIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3',4''-dioctyl-2,2':5',2'':5'',2'''-tetrathienyl 在 四(三苯基膦)钯 、 tetrakis(triphenylarsine)palladium(0) N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 、 氯仿 、 水 、 1,2-二氯乙烷 为溶剂， 反应 73.0h， 生成 3'',4'''-dioctyl-5'''''-(diphenylamino)-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene-5-carboxaldehyde
  参考文献：
  名称：

  Λ-Type Regioregular Oligothiophenes:  Synthesis and Second-Order NLO Properties

  摘要：

  The synthesis of a new series of Lambda-type, D-Pi-A regioregular oligothiophenes is described. The simultaneous presence of the chiral centers and the Lambda-type structure disfavored the formation of centro-symmetrical dimeric assemblies. Hence, enhanced first hyperpolarizabilities beta(HRS) were measured in comparison with those of the corresponding monomers.

  DOI：

  10.1021/jo070888a
• 作为产物：
  描述：

  2-溴-3-辛基噻吩 在 palladium diacetate 、 palladium diacetate 偶氮二异丁腈 、 四丁基溴化铵 、 碘 、 三正丁基氢锡 、 potassium carbonate 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 9.0h， 生成 3',4''-dioctyl-2,2':5',2'':5'',2'''-tetrathienyl
  参考文献：
  名称：

  Palladium-catalyzed coupling reactions towards the synthesis of well-defined thiophene-oligomers

  摘要：

  Heck- and Ullmann-type palladium-catalyzed reactions were used in order to perform the synthesis of 3',4"-dioctyl-2,2',5'2",5",2"'-tetrathienyl. The desired oligothiophene was synthesized in five steps with a total yield of 38% by a Heck-type reaction of bromo-derivatives and a yield of 45% by an Ullmann-type reaction of iodo-precursors. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00626-0

文献信息

• Palladium-catalyzed coupling reactions towards the synthesis of well-defined thiophene-oligomers
  作者：Jwanro Hassan、Christel Gozzi、Emmanuelle Schulz、Marc Lemaire

  DOI：10.1016/s0022-328x(03)00626-0

  日期：2003.12

  Heck- and Ullmann-type palladium-catalyzed reactions were used in order to perform the synthesis of 3',4"-dioctyl-2,2',5'2",5",2"'-tetrathienyl. The desired oligothiophene was synthesized in five steps with a total yield of 38% by a Heck-type reaction of bromo-derivatives and a yield of 45% by an Ullmann-type reaction of iodo-precursors. (C) 2003 Elsevier B.V. All rights reserved.
• Λ-Type Regioregular Oligothiophenes:  Synthesis and Second-Order NLO Properties
  作者：Samia Zrig、Guy Koeckelberghs、Thierry Verbiest、Bruno Andrioletti、Eric Rose、André Persoons、Inge Asselberghs、Koen Clays

  DOI：10.1021/jo070888a

  日期：2007.7.1

  The synthesis of a new series of Lambda-type, D-Pi-A regioregular oligothiophenes is described. The simultaneous presence of the chiral centers and the Lambda-type structure disfavored the formation of centro-symmetrical dimeric assemblies. Hence, enhanced first hyperpolarizabilities beta(HRS) were measured in comparison with those of the corresponding monomers.