3'',4''-dihexyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene | 196800-60-9

• 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''-dihexyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
• 英文别名: 3,4-Dihexyl-2,5-bis(5-thiophen-2-ylthiophen-2-yl)thiophene
• CAS: 196800-60-9
• 化学式: C₃₂H₃₆S₅
• 分子量: 580.968
• InChiKey: DOGYVZMWRZIAML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-噻吩硼酸 、 在 tris-(dibenzylideneacetone)dipalladium(0) 、 3-(dicyclohexylphosphino)-1-methyl-2-phenyl-1H-indole 、 caesium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以82%的产率得到3'',4''-dihexyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
  参考文献：
  名称：

  卤代噻吩基的配体激活的Pd催化的Suzuki-Miyaura偶联合成基于噻吩的π共轭低聚物。

  摘要：

  证明了具有配体活性的Pd催化的卤代噻吩基的Suzuki-Miyaura偶联可合成包括噻吩基噻吩在内的各种基于噻吩的π共轭低聚物。吲哚基膦配体在该转化中起重要作用。噻吩硼酸得到了很好的应用，这可能为噻吩硼酸在材料化学中基于噻吩的π共轭低聚物的合成中的应用开辟了一个窗口。

  DOI：

  10.1002/asia.201800395

文献信息

• Oligothiophene Functionalized Dimethyldihydropyrenes I: Syntheses and Photochromicity
  作者：Stephen G. Robinson、Vittorio A. Sauro、Reginald H. Mitchell

  DOI：10.1021/jo901070y

  日期：2009.9.4

  The syntheses of 2,7-di-tert-butyldimethyldihydrobenzo[e]pyrenes with thienyl (6), terthienyl (7), and pentathienyl (14) side chains at the 4,5- positions, ter- and pentathienyl side chains at the 4-position with ter- (39) and pentathienylcarbonyl (40) side chains at the 10- and 11-positions, 2-naphthoyl-7-tert-butyldimethyldihydropyrenes with ter- (53), penta- (54), and septithienyl (55) side chains at the 4,9-positions are described. These compounds are all photochromic and open to the corresponding cyclophanedienes with long wavelength ( > 490 nm) light, and as such, the conjugative path could change considerably, making them suitable to investigate as potentially switchable conducting molecules. In this paper, the syntheses and the photochemical and thermal isomerizations are studied in the accompanying paper, the electrochemical and conductive properties are studied. Here, a comparison of the relative opening rates to that of the benzo[e]pyrene 4 (with no thienyl substituents) is made, and all of the above photochromes show considerably enhanced photo-opening of the DHPs to the CPDs. As examples, 14, 40, and 54 were cycled between the open and closed forms, and no decomposition was observed; however, when 54 was irradiated for 40 h with 254 nm light, some radicals did form, which enhanced the thermal closing rate, and so extensive irradiation with short wave UV is better avoided. The thermal closing reactions were also studied, and all of the above compounds close faster than benzo-CPD 4', though for the highly photochromic ter- and pentathienyl benzo-CPDs 39' and 40', the rate was not too enhanced from that of 4' and so are probably the best compromise between fast photochromicity and slow thermal reversion.
• ORGANIC PHOTOELECTRIC CONVERSION ELEMENT
  申请人：Uetani Yasunori

  公开号：US20120100285A1

  公开（公告）日：2012-04-26

  An organic photoelectric conversion element having a high absorbance at 600 nm can be provide by a method for manufacturing an organic photoelectric conversion element having a pair of electrodes at least one of which is transparent or translucent, and an organic layer between the electrodes, the method comprising a step of applying a solution that contains a conjugated polymer compound having a thiophenediyl group as a repeating unit and a sulfur-containing heterocyclic compound on one of the electrodes to form an applied film, and a step of drying the applied film at a temperature of 70° C. or less to form the organic layer.
• US8723163B2
  申请人：——

  公开号：US8723163B2

  公开（公告）日：2014-05-13
• Synthesis of Thiophene‐Based π‐Conjugated Oligomers via Ligand‐Enabled Pd‐Catalyzed Suzuki–Miyaura Coupling of Haloterthienyls
  作者：Jie Guo、Yong Wu、Fuk Yee Kwong、Heng Zhang、Aiwen Lei

  DOI：10.1002/asia.201800395

  日期：2018.7.4

  A ligand‐enabled Pd‐catalyzed Suzuki–Miyaura coupling of haloterthienyls for the synthesis of various thiophene‐based π‐conjugated oligomers including quinquethiophenes is demonstrated. An indolyl phosphine ligand plays an important role in this transformation. Thiopheneboronic acids were well applied, which might open up a window for the application of thiopheneboronic acids in the synthesis of thiophene‐based

  证明了具有配体活性的Pd催化的卤代噻吩基的Suzuki-Miyaura偶联可合成包括噻吩基噻吩在内的各种基于噻吩的π共轭低聚物。吲哚基膦配体在该转化中起重要作用。噻吩硼酸得到了很好的应用，这可能为噻吩硼酸在材料化学中基于噻吩的π共轭低聚物的合成中的应用开辟了一个窗口。