3-octyl-5-[3-octyl-5-[4-[4-octyl-5-[4-octyl-5-[5-[5-[3-octyl-5-(3-octylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]buta-1,3-diynyl]thiophen-2-yl]-2-[5-[5-[3-octyl-5-(3-octylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophene | 217637-19-9

• 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-octyl-5-[3-octyl-5-[4-[4-octyl-5-[4-octyl-5-[5-[5-[3-octyl-5-(3-octylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]buta-1,3-diynyl]thiophen-2-yl]-2-[5-[5-[3-octyl-5-(3-octylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophene
• CAS: 217637-19-9
• 化学式: C₁₁₆H₁₅₄S₁₂
• 分子量: 1933.29
• InChiKey: RUYBZVRUEBXRKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  49.9
• 重原子数：
  128
• 可旋转键数：
  69
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  339
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-octyl-5-[3-octyl-5-[4-[4-octyl-5-[4-octyl-5-[5-[5-[3-octyl-5-(3-octylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]buta-1,3-diynyl]thiophen-2-yl]-2-[5-[5-[3-octyl-5-(3-octylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophene 在 sodium sulfide 作用下， 以72%的产率得到3-Octyl-5-[3-octyl-5-[5-[4-octyl-5-[4-octyl-5-[5-[5-[3-octyl-5-(3-octylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-2-[5-[5-[3-octyl-5-(3-octylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophene
  参考文献：
  名称：

  Synthesis, Optical, and Conductive Properties of Long Oligothiophenes and Their Utilization as Molecular Wires

  摘要：

  本报告回顾了涉及 48 聚体和 72 聚体（对应于单分散聚合物）的超长低聚噻吩的当前发展。同系物的系统研究为α-共轭噻吩体系的光学和导电性质提供了有价值的信息：有效共轭长度在中性态下延伸至约20个噻吩单元，在氧化态下延伸至约30个噻吩单元；这个长度在确定电子结构和电导率方面起着至关重要的作用。此外，活性电荷载体物种都是π-二聚体和链二聚体，并且电荷传输通过这两种物种的变形发生。该描述还描述了低聚噻吩作为允许光诱导电子和/或能量转移的分子线是多么有用。演示了在末端 α-位置用供体单元和受体单元功能化的复杂低聚噻吩的分子线行为。

  DOI：

  10.1246/bcsj.74.1789
• 作为产物：
  描述：

  5-ethynyl-3,4',3'''',3'''''-tetraoctyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene 在 copper diacetate 作用下， 以 吡啶 为溶剂， 以92%的产率得到3-octyl-5-[3-octyl-5-[4-[4-octyl-5-[4-octyl-5-[5-[5-[3-octyl-5-(3-octylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]buta-1,3-diynyl]thiophen-2-yl]-2-[5-[5-[3-octyl-5-(3-octylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophene
  参考文献：
  名称：

  Synthesis, Optical, and Conductive Properties of Long Oligothiophenes and Their Utilization as Molecular Wires

  摘要：

  本报告回顾了涉及 48 聚体和 72 聚体（对应于单分散聚合物）的超长低聚噻吩的当前发展。同系物的系统研究为α-共轭噻吩体系的光学和导电性质提供了有价值的信息：有效共轭长度在中性态下延伸至约20个噻吩单元，在氧化态下延伸至约30个噻吩单元；这个长度在确定电子结构和电导率方面起着至关重要的作用。此外，活性电荷载体物种都是π-二聚体和链二聚体，并且电荷传输通过这两种物种的变形发生。该描述还描述了低聚噻吩作为允许光诱导电子和/或能量转移的分子线是多么有用。演示了在末端 α-位置用供体单元和受体单元功能化的复杂低聚噻吩的分子线行为。

  DOI：

  10.1246/bcsj.74.1789

文献信息

• Synthesis, Optical, and Conductive Properties of Long Oligothiophenes and Their Utilization as Molecular Wires
  作者：Tetsuo Otsubo、Yoshio Aso、Kazuo Takimiya

  DOI：10.1246/bcsj.74.1789

  日期：2001.10

  This account reviews the current development of extraordinarily long oligothiophenes involving the 48-mer and 72-mer, which correspond to mono-disperse polymers. The systematic studies of the homologous series have provided valuable information on the optical and conductive properties of α-conjugated thiophene systems: an effective conjugation length extends to around 20 thiophene units in the neutral state and around 30 thiophene units in the oxidation state; this length plays a critical role in determining the electronic structures and conductivities. In addition, the active charge carrier species are both π-dimers and chain dimers, and charge transport occurs through the transfiguration of both species. This account also describes how useful oligothiophenes are as molecular wires allowing photoinduced electron- and/or energy-transfer. The molecular-wire behaviors of sophisticated oligothiophenes that are functionalized with a donor unit and an acceptor unit at the terminal α-positions are demonstrated.

  本报告回顾了涉及 48 聚体和 72 聚体（对应于单分散聚合物）的超长低聚噻吩的当前发展。同系物的系统研究为α-共轭噻吩体系的光学和导电性质提供了有价值的信息：有效共轭长度在中性态下延伸至约20个噻吩单元，在氧化态下延伸至约30个噻吩单元；这个长度在确定电子结构和电导率方面起着至关重要的作用。此外，活性电荷载体物种都是π-二聚体和链二聚体，并且电荷传输通过这两种物种的变形发生。该描述还描述了低聚噻吩作为允许光诱导电子和/或能量转移的分子线是多么有用。演示了在末端 α-位置用供体单元和受体单元功能化的复杂低聚噻吩的分子线行为。
• Synthesis and Properties of the Longest Oligothiophenes:  The Icosamer and Heptacosamer
  作者：Hidetaka Nakanishi、Naoto Sumi、Yoshio Aso、Tetsuo Otsubo

  DOI：10.1021/jo981541y

  日期：1998.11.1
• Synthesis and Properties of a Series of the Longest Oligothiophenes up to the 48-mer
  作者：Naoto Sumi、Hidetaka Nakanishi、Shinpei Ueno、Kazuo Takimiya、Yoshio Aso、Tetsuo Otsubo

  DOI：10.1246/bcsj.74.979

  日期：2001.5

  A series of the longest class of oligothiophenes extended at intervals of seven thiophene units from the 6-mer up to the 48-mer has been synthesized by a combination of the random Eglinton coupling reaction of mono- and di-ethynylsexithiophenes and a subsequent sodium sulfide-induced cyclization reaction of the resulting oligo(sexithienylene-diethynylene)s. Their structures were well characterized by MALDI-TOF MS and 1H NMR spectroscopy. The molecular weights of the oligothiophenes and oligo(sexithienylene-diethynylene)s, measured by gel-permeation liquid chromatography using the polystyrene standard, are nearly double the actual ones, indicating that they keep highly rigid rod-type shapes. According to a molecular model, the molecular lengths of the longest oligothiophene 48-mer and the longest oligo(sexithienylene-diethynylene) reach approximately 18.6 nm and 25.0 nm, respectively. In the electronic absorption and emission spectra, the π–π* transitions of the oligothiophenes demonstrate progressive red shifts with increasing chain length up to the 20-mer. In the cyclic voltammograms, furthermore, the first oxidation potentials tend to continue negative shifts up to the 34-mer. In accordance with these spectral changes, the doped conductivities steadily increase and approach that of a structurally related polymer.

  通过单乙炔基和二乙炔基噻吩的无规埃格林顿偶联反应，以及随后硫化钠诱导的低聚（噻吩-二乙炔）环化反应，合成了一系列最长的低聚噻吩，这些低聚噻吩从 6-聚合体一直延伸到 48-聚合体，每隔 7 个噻吩单元。它们的结构通过 MALDI-TOF MS 和 1H NMR 光谱得到了很好的表征。以聚苯乙烯为标准，通过凝胶渗透液相色谱法测得的低聚噻吩和低聚(sexithienylene-diethynylene)s 的分子量几乎是实际分子量的两倍，表明它们保持着高刚性的棒状形状。根据分子模型，最长的低聚噻吩 48-mer 和最长的低聚（sexithienylene-diethynylene）的分子长度分别约为 18.6 nm 和 25.0 nm。在电子吸收光谱和发射光谱中，低聚噻吩的 π-π* 转变随着链长的增加而逐渐发生红移，直至 20-mer。此外，在循环伏安图中，第一氧化电位趋于继续负移，直至 34 个聚合物。根据这些光谱变化，掺杂后的电导率稳步上升，并接近结构相关聚合物的电导率。