5-(4-bromobutyl)-2,2':5',2''-terthiophene | 787583-67-9

• 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: 5-(4-bromobutyl)-2,2':5',2''-terthiophene
• 英文别名: 2-(4-bromobutyl)-5-(5-(thiophen-2-yl)thiophen-2-yl)thiophene；2-(4-Bromobutyl)-5-(5-thiophen-2-ylthiophen-2-yl)thiophene
• CAS: 787583-67-9
• 化学式: C₁₆H₁₅BrS₃
• 分子量: 383.397
• InChiKey: WPYGXPWYVJBQQD-UHFFFAOYSA-N

物化性质

• 熔点：
  60-62 °C
• 沸点：
  467.3±45.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-bromobutyl)-2,2':5',2''-terthiophene 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 68.0h， 生成
  参考文献：
  名称：

  Spacer length dependence of photoinduced electron transfer in heterosupramolecular assemblies of TiO2 nanoparticles and terthiophene

  摘要：

  已制备并研究了通过5、9和13个单键饱和间隔子连接的TiO2纳米粒子（<3 nm）和荧光共轭三噻吩低聚物的异质超分子组装体，以探讨混合有机-无机系统中光诱导电荷转移的距离依赖性。在氯仿中，这些低聚物-TiO2偶联体的电荷转移速率随着间隔子长度的增加从2.5 × 1010降低到1.6 × 109 s−1。因此，即使是最长的连接子，电荷转移也相对较快。速率常数并不随间隔子长度简单地呈指数衰减，每个键的衰减对数值相对较低（0.3 < β < 0.6）。这一效应可归因于纳米粒子表面的近邻烷基链对电子耦合的逆向折叠或放大作用。

  DOI：

  10.1039/b405424e
• 作为产物：
  描述：

  1,4-二溴丁烷 、 alpha-三联噻吩 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.17h， 以42%的产率得到5-(4-bromobutyl)-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Spacer length dependence of photoinduced electron transfer in heterosupramolecular assemblies of TiO2 nanoparticles and terthiophene

  摘要：

  已制备并研究了通过5、9和13个单键饱和间隔子连接的TiO2纳米粒子（<3 nm）和荧光共轭三噻吩低聚物的异质超分子组装体，以探讨混合有机-无机系统中光诱导电荷转移的距离依赖性。在氯仿中，这些低聚物-TiO2偶联体的电荷转移速率随着间隔子长度的增加从2.5 × 1010降低到1.6 × 109 s−1。因此，即使是最长的连接子，电荷转移也相对较快。速率常数并不随间隔子长度简单地呈指数衰减，每个键的衰减对数值相对较低（0.3 < β < 0.6）。这一效应可归因于纳米粒子表面的近邻烷基链对电子耦合的逆向折叠或放大作用。

  DOI：

  10.1039/b405424e

文献信息

• 一种低聚噻吩衍生物及其应用
  申请人：南方医科大学

  公开号：CN104496962B

  公开（公告）日：2017-01-04

  本发明属于有机化学领域，具体涉及一种低聚噻吩衍生物，其分子结构如下式(Ⅰ)所示，式中R1是氢，3‑溴丙基，4‑溴丁基，3‑氨基丙基，4‑氨基丁基，3‑叠氮基丙基，4‑叠氮基丁基，3‑(3‑氟‑5‑(三氟甲基)苯甲酰胺基)丙基和4‑(3‑氟‑5‑(三氟甲基)苯甲酰胺基)丁基其中一种；R2是氢，3‑溴丙基，4‑溴丁基，3‑氨基丙基，4‑氨基丁基，3‑叠氮基丙基和4‑叠氮基丁基其中一种；n＝1,2,3或者4。本发明所述的低聚噻吩衍生物具有抑制流感病毒的效果。
• Oligothiophene compounds inhibit the membrane fusion between H5N1 avian influenza virus and the endosome of host cell
  作者：Zhibo Zhu、Zhili Yao、Xiantian Shen、Zhipeng Chen、Xiangtao Liu、Jon R. Parquette、Shuwen Liu

  DOI：10.1016/j.ejmech.2017.02.040

  日期：2017.4

  Hemagglutinin (HA) which is essential for influenza viral infection and replication has become a target for the design of anti-influenza drugs. A novel series of oligothiophene compounds focused on the target were synthesized as specific inhibitors against the H5 subtype of influenza A viruses because oligothiophene has Pi-Pi stronger pep interactions with residues F110(2) and M24(1) of HA2 side chains. Oligothiophene compounds were designed and synthesized by a series of alkylation, azidation, amination and amidation reactions. The entry inhibitory activities of those compounds were tested at a cellular level against H5N1 influenza pseudovirus. Compound 3sf was revealed as the most active inhibitor in this series with an IC50 of 0.029 mM. The activity of 3sf is almost 1000 times that of the positive reference compound (CL-385319). A structure-activity analysis of these compounds demonstrated that the size of the oligothiophene compounds was very important for the inhibitory activity. Four compounds (3sk, 3sf, 3sc and 4sc) of strong inhibitiory activity against H5N1 influenza pseudovirus were assessed against H1N1 influenza virus MDCK. They also showed strong inhibitiory activity with IC50s of 3.292 mu M, 1.240 mu M, 1.119 mu M and 0.768 mu M, respectively. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Tunneling Probability Increases with Distance in Junctions Comprising Self-Assembled Monolayers of Oligothiophenes
  作者：Yanxi Zhang、Saurabh Soni、Theodorus L. Krijger、Pavlo Gordiichuk、Xinkai Qiu、Gang Ye、Harry T. Jonkman、Andreas Herrmann、Karin Zojer、Egbert Zojer、Ryan C. Chiechi

  DOI：10.1021/jacs.8b09793

  日期：2018.11.7

  Molecular tunneling junctions should enable the tailoring of charge-transport at the quantum level through synthetic chemistry but are hindered by the dominance of the electrodes. We show that the frontier orbitals of molecules can be decoupled from the electrodes, preserving their relative energies in self-assembled monolayers even when a top-contact is applied. This decoupling leads to the remarkable observation of tunneling probabilities that increase with distance in a series of oligothiophenes, which we explain using a two-barrier tunneling model. This model is generalizable to any conjugated oligomers for which the frontier orbital gap can be determined and predicts that the molecular orbitals that dominate tunneling charge-transport can be positioned via molecular design rather than by domination of Fermi-level pinning arising from strong hybridization. The ability to preserve the electronic structure of molecules in tunneling junctions facilitates the application of well-established synthetic design rules to tailor the properties of molecular-electronic devices.