5"'-bromo-3,3"'-dihexyl-2,2':5',2":5",2"'-quaterthiophene-5-carbaldehyde | 796867-49-7

• 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: 5"'-bromo-3,3"'-dihexyl-2,2':5',2":5",2"'-quaterthiophene-5-carbaldehyde
• 英文别名: 5-[5-[5-(5-Bromo-3-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]-4-hexylthiophene-2-carbaldehyde
• CAS: 796867-49-7
• 化学式: C₂₉H₃₃BrOS₄
• 分子量: 605.748
• InChiKey: HCTSBHKJDZQATJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5"'-bromo-3,3"'-dihexyl-2,2':5',2":5",2"'-quaterthiophene-5-carbaldehyde 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.5h， 生成 3,3'''-dihexyl-5'''-ethynyl-[2,2':5',2'':5'',2'''-quaterthiophene]-5-carboxaldehyde
  参考文献：
  名称：

  Thieno[3,4-d]imidazolium-containing Molecular Wire: Switching Behavior of Photoinduced Intramolecular Electron Transfer

  摘要：

  已经合成了锌-卟啉-寡噻吩-富勒烯三元复合体，其中二乙炔基噻吩[3,4-d]咪唑离子作为寡噻吩的中心单元。通过将咪唑盐中的对离子从I−置换为F−，观察到锌-卟啉单元的荧光显著增强，表明光诱导的分子内电子转移可以通过对该单元的电子扰动来控制。

  DOI：

  10.1246/cl.2006.1366
• 作为产物：
  描述：

  5,5'-二溴-2,2'-联噻吩 在 N-溴代丁二酰亚胺(NBS) 、 magnesium 、 三氯氧磷 作用下， 以 二硫化碳 、 乙醚 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 5"'-bromo-3,3"'-dihexyl-2,2':5',2":5",2"'-quaterthiophene-5-carbaldehyde
  参考文献：
  名称：

  二茂铁-低聚噻吩-富勒烯三联体的合成和光物理性质

  摘要：

  为了促进以前在低聚噻吩-富勒烯二聚体（nT-C60）中观察到的光诱导电荷分离，我们设计了在低聚噻吩的未取代末端位点上带有强电子给体的二茂铁的附加附件，并合成了两种类型的二茂铁-低聚噻吩-富勒烯三联体，Fc-nT-C60将二茂铁直接连接至低聚噻吩，而Fc-tm-nT-C60在三茂铁与低聚噻吩之间插入三亚甲基间隔基。对于三联体的中央寡聚噻吩，有一系列同源的四噻吩（4T），辛噻吩（8T）和十二聚噻吩（12T））进行系统地检查。Fc-nT-C60的循环伏安图和电子吸收光谱表明二茂铁和低聚噻吩组分之间的共轭。在甲苯中测得的Fc-nT-C60的发射光谱表明，与二重体nT-C60相比，寡噻吩的荧光显着淬灭。用分子内电子转移参与光物理衰变过程来解释这种猝灭。另外共轭的二茂铁显然有助于电荷分离态的稳定，从而促进了分子内电子的转移。通过观察非共轭三联体Fc-tm-nT-C60的发射光谱可以证实这一点与相应的二元组nT-C60基本相似。

  DOI：

  10.1021/jo049137o

文献信息

• Synthesis and Photovoltaic Properties of Tetrathiafulvalene–Oligothiophene–Fullerene Triads
  作者：Hiroki Kanato、Masashi Narutaki、Kazuo Takimiya、Tetsuo Otsubo、Yutaka Harima

  DOI：10.1246/cl.2006.668

  日期：2006.6

  Novel tetrathiafulvalene–oligothiophene–fullerene triads have been synthesized as single-component materials for photovoltaic cells. They showed somewhat improved photovoltaic performances, when co...

  新型四硫富瓦烯-低聚噻吩-富勒烯三元组已被合成为光伏电池的单组分材料。它们显示出一些改善的光伏性能，当...
• Organic Dyes Incorporating the Dithieno[3,2-<i>b</i>:2′,3′-<i>d</i>]thiophene Moiety for Efficient Dye-Sensitized Solar Cells
  作者：Hsiu-Yi Yang、Yung-Sheng Yen、Ying-Chan Hsu、Hsien-Hsin Chou、Jiann T. Lin

  DOI：10.1021/ol902327p

  日期：2010.1.1

  New dipolar compounds incorporating a dithieno[3,2-b:2′,3′-d]thiophene unit as the electron donor, an oligothiophene moiety as the conjugated spacer, and 2-cyanoacrylic acid as the electron acceptor have been synthesized. These nonarylamine type metal-free organic compounds have been successfully used as the sensitizers of dye-sensitized solar cells (DSSCs). The conversion efficiencies of the DSSCs

  合成了以二噻吩并[3,2-b：2'，3'- d ]噻吩单元作为电子供体，低聚噻吩部分作为共轭间隔基和2-氰基丙烯酸作为电子受体的新型偶极化合物。这些非芳基胺型无金属有机化合物已成功用作染料敏化太阳能电池（DSSC）的敏化剂。在AM 1.5 G辐照下，DSSC的转化效率范围为3.54至5.15％。在相似条件下制造和测量的钌染料基于N719的标准电池的最佳效率约为70％。
• Synthesis and Photophysical Properties of Two Dual Oligothiophene-Fullerene Linkage Molecules as Photoinduced Long-Distance Charge Separation Systems
  作者：Masashi Narutaki、Kazuo Takimiya、Tetsuo Otsubo、Yutaka Harima、Huimin Zhang、Yasuyuki Araki、Osamu Ito

  DOI：10.1021/jo051821v

  日期：2006.3.1

  To further extend photoinduced charge separation previously observed for olio-othiophene-fullerene dyads (nT-C-60), we have studied two novel dual oligothiophene-fullerene triads, 8T-4T-C-60 and 4T-8T-C-60, where quaterthiophene (4T) and octithiophene (8T) are linked by a trimethylene chain and either one is attached to a fullerene (C-60). The cyclic voltanirnograrns and electronic absorption spectra of these triad compounds indicated no electronic interactions among, the three components. On the other hand, the emission spectra were markedly perturbed by electron transfer and/or energy transfer from the oligothiophene to fullerene. Detailed comparisons between the emission spectra of the triads (8T-4T-C-60 and 4T-8T-C-60) and the dyads (4T-C-60 and 8T-C-60) suggest that the additionally attached octithiophene or quaterthiophene in the triads is involved in the photophysical decay mechanism, and the 8T-4T-C-60 triad undergoes photoinduced electron transfer leading to long-distance charge separation. This was actually corroborated by observation of the specific bands due to 8T(.+)-4T-C-60(.-) species in the transient absorption spectra after photoexcitation of the octithiophene. The sandwich device based on the 8T-4T-C-60 triad produced a more effective photovoltaic response to visible light owing to the contribution of the additional octithiophene chromophore compared to that using the dyad 4T-C-60. On the other hand, the 4T-8T-C60- based device demonstrated a rather poorer photovoltaic performance when compared to the 8T-C-60 device.
• Synthesis and Photophysical Properties of Ferrocene−Oligothiophene−Fullerene Triads
  作者：Hiroki Kanato、Kazuo Takimiya、Tetsuo Otsubo、Yoshio Aso、Takumi Nakamura、Yasuyuki Araki、Osamu Ito

  DOI：10.1021/jo049137o

  日期：2004.10.1

  the involvement of intramolecular electron transfer in the photophysical decay process. The additionally conjugated ferrocene evidently contributes to the stabilization of charge separation states, thus promoting intramolecular electron transfer. This is corroborated by the observation that the emission spectra of the nonconjugated triads Fc-tm-nT-C60 are essentially similar to the corresponding dyads

  为了促进以前在低聚噻吩-富勒烯二聚体（nT-C60）中观察到的光诱导电荷分离，我们设计了在低聚噻吩的未取代末端位点上带有强电子给体的二茂铁的附加附件，并合成了两种类型的二茂铁-低聚噻吩-富勒烯三联体，Fc-nT-C60将二茂铁直接连接至低聚噻吩，而Fc-tm-nT-C60在三茂铁与低聚噻吩之间插入三亚甲基间隔基。对于三联体的中央寡聚噻吩，有一系列同源的四噻吩（4T），辛噻吩（8T）和十二聚噻吩（12T））进行系统地检查。Fc-nT-C60的循环伏安图和电子吸收光谱表明二茂铁和低聚噻吩组分之间的共轭。在甲苯中测得的Fc-nT-C60的发射光谱表明，与二重体nT-C60相比，寡噻吩的荧光显着淬灭。用分子内电子转移参与光物理衰变过程来解释这种猝灭。另外共轭的二茂铁显然有助于电荷分离态的稳定，从而促进了分子内电子的转移。通过观察非共轭三联体Fc-tm-nT-C60的发射光谱可以证实这一点与相应的二元组nT-C60基本相似。
• Thieno[3,4-<i>d</i>]imidazolium-containing Molecular Wire: Switching Behavior of Photoinduced Intramolecular Electron Transfer
  作者：Yutaka Ie、Tetsuro Kawabata、Takahiro Kaneda、Yoshio Aso

  DOI：10.1246/cl.2006.1366

  日期：2006.12

  Zinc–porphyrin–oligothiophene–fullerene triad, where diethynylthieno[3,4-d]imidazolium is incorporated as a central unit of oligothiophene, has been synthesized. A dramatic enhancement of fluorescence from the zinc–porphyrin unit was observed on displacing counter anion from I− to F− in the imidazolium salt, indicating that photoinduced intramolecular electron transfer is controllable by the electronic perturbation to this unit.

  已经合成了锌-卟啉-寡噻吩-富勒烯三元复合体，其中二乙炔基噻吩[3,4-d]咪唑离子作为寡噻吩的中心单元。通过将咪唑盐中的对离子从I−置换为F−，观察到锌-卟啉单元的荧光显著增强，表明光诱导的分子内电子转移可以通过对该单元的电子扰动来控制。