3,3'',3'''',4,4'',4''''-Hexabutyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene | 321853-04-7

• 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: 3,3'',3'''',4,4'',4''''-Hexabutyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
• 英文别名: 3,4-Dibutyl-2,5-bis[5-(3,4-dibutylthiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 321853-04-7
• 化学式: C₄₄H₆₀S₅
• 分子量: 749.29
• InChiKey: RTSVOOFTXBEJMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.4
• 重原子数：
  49
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3'',3'''',4,4'',4''''-Hexabutyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene 在 Hg(CH₃COO)2 、 碘 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以87%的产率得到5,5''''-diiodo-3,3'',3'''',4,4'',4''''-hexabutyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
  参考文献：
  名称：

  Homologous series of regioregular alkylsubstituted oligothiophenes up to an 11-mer

  摘要：

  A complete series of structurally well-defined butylated oligothiophenes up to an Il-mer was synthesized by a combination of aryl-aryl cross-coupling reactions and cyclization of 1,3-butadiyne precursors with sulfide anions. Palladium-catalyzed cross-coupling of halogenated thiophene units with trimethylsilylacetylene effectively yields ethynylated thiophenes which after deprotection are oxidatively coupled to the corresponding 1,3-butadiynes. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00254-x
• 作为产物：
  描述：

  3,4-二丁基噻吩 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) N-溴代丁二酰亚胺(NBS) 、 magnesium 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 3,3'',3'''',4,4'',4''''-Hexabutyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
  参考文献：
  名称：

  Homologous series of regioregular alkylsubstituted oligothiophenes up to an 11-mer

  摘要：

  A complete series of structurally well-defined butylated oligothiophenes up to an Il-mer was synthesized by a combination of aryl-aryl cross-coupling reactions and cyclization of 1,3-butadiyne precursors with sulfide anions. Palladium-catalyzed cross-coupling of halogenated thiophene units with trimethylsilylacetylene effectively yields ethynylated thiophenes which after deprotection are oxidatively coupled to the corresponding 1,3-butadiynes. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00254-x

文献信息

• Synthesis and electronic properties of series of oligothiophene-[1,10]phenanthrolines
  作者：Martin Ammann.、Peter Bäuerle

  DOI：10.1039/b508572a

  日期：——

  of a general interest in organic materials chemistry. In this paper, we describe a straightforward synthetic procedure, which gives access to a series of 2-(oligothienyl)-[1,10]phenanthrolines (nT-phen), 2,9-bis(oligothienyl)-[1,10]phenanthrolines (nT-phen-nT) and 2,2'-(oligothienyl)bis-[1,10]phenanthrolines (phen-nT-phen). By a Negishi-type cross coupling of 2-iodo-[1,10]phenanthroline or 2,9-diiodo-[1

  在其分子主链中包含金属结合位点的有机半导体在有机材料化学中是普遍关注的。在本文中，我们描述了一种简单的合成程序，该程序可访问一系列2-（oligothienyl）-[1,10] phenothrolines（nT-phen），2,9-bis（oligothienyl）-[1,10]菲咯啉（nT-phen-nT）和2,2'-（低聚噻吩基）双-[1,10]菲咯啉（phen-nT-phen）。通过将2-碘-[1,10]菲咯啉或2,9-二碘-[1,10]菲咯啉与原位生成的不同单，三和五喹噻吩的α-锌衍生物进行Negishi型交叉偶联，我们能够在中等条件下合成相应的寡噻吩基-菲咯啉，从而获得优异的收率。此外，对新材料的光学性质的表征表明，这两个亚基 寡聚噻吩和菲咯啉在π结合中。氧化还原特性的表征揭示了[1,10]菲咯啉作为nT-phen-nT系列中pi桥联单元的作用的其他证据。
• Synthesis of the First Fullyα-Conjugated Macrocyclic Oligothiophenes: Cyclo[n]thiophenes with Tunable Cavities in the Nanometer Regime
  作者：Jens Krömer、Idoia Rios-Carreras、Gerda Fuhrmann、Christiane Musch、Markus Wunderlin、Tony Debaerdemaeker、Elena Mena-Osteritz、Peter Bäuerle

  DOI：10.1002/1521-3773(20001002)39:19<3481::aid-anie3481>3.0.co;2-o

  日期：2000.10.2
• Homologous series of regioregular alkylsubstituted oligothiophenes up to an 11-mer
  作者：Jens Krömer、Peter Bäuerle

  DOI：10.1016/s0040-4020(01)00254-x

  日期：2001.4

  A complete series of structurally well-defined butylated oligothiophenes up to an Il-mer was synthesized by a combination of aryl-aryl cross-coupling reactions and cyclization of 1,3-butadiyne precursors with sulfide anions. Palladium-catalyzed cross-coupling of halogenated thiophene units with trimethylsilylacetylene effectively yields ethynylated thiophenes which after deprotection are oxidatively coupled to the corresponding 1,3-butadiynes. (C) 2001 Published by Elsevier Science Ltd.