5''-bromo-5-hexyl-[2,2';5',2'']terthiophene | 524937-20-0

• 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-5-hexyl-[2,2';5',2'']terthiophene
• 英文别名: 2-Bromo-5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 524937-20-0
• 化学式: C₁₈H₁₉BrS₃
• 分子量: 411.451
• InChiKey: SHDVROMCMPNBAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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''-bromo-5-hexyl-[2,2';5',2'']terthiophene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 5-hexyl-5''-vinyl-2,2';5',2''-terthiophene
  参考文献：
  名称：

  Poly(α-vinyl-ω-alkyloligothiophene) Side-Chain Polymers. Synthesis, Fluorescence, and Morphology

  摘要：

  The synthesis of polyvinyl polymers by radical polymerization of alpha-vinyl-omega-alkyl-terminated thiophene and bi-, ter-, and quaterthiophenes is reported. The photoluminescence properties of the polymers in solution and in thin film are described. In thin film, self-assembly-induced white photoluminescence was observed for poly(5-vinyl-5"'-hexylquaterthiophene). For this polymer, single crystals with rectangular shape and micrometer size were obtained by drop casting from CS2. MM3 calculations on model diads and triads indicate that, on increasing the size of the side groups, van der Waals interactions promote the stacking of the pendants on the same side of the polyvinyl chain.

  DOI：

  10.1021/ma049102q
• 作为产物：
  描述：

  2-正己基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 5''-bromo-5-hexyl-[2,2';5',2'']terthiophene
  参考文献：
  名称：

  具有正己基端基的四面体寡聚噻吩的合成，电子和形态学性质

  摘要：

  一系列在末端噻吩环的α位带有正己基的四面体寡聚噻吩（（n- C 6 H 13（C 4 H 2 S）n）4 C（Hex-T n TM; n = 1– 4）是由Kosugi–Migita–Stille耦合合成的，是一个关键反应。由于末端正己基团提供了更高的溶解度，因此成功获得了最大的同系物（n = 4）。较小的导数（n = 1，2）是液态物质，而较大的导数（n＝ 3，4）为固体。Hex-T3 TM可能是由于堆积力而在晶体中的相邻噻吩环之间部分采用了顺式构象。Hex‐T3 TM不仅以结晶态出现，而且以非晶态出现，在高达80°C的温度下稳定。无论端基如何，与相应的线性类似物相比，n = 2的衍生物均显示具有大的斯托克斯位移的宽荧光，从而表明联噻吩部分之间存在分子内相互作用。通过循环伏安法测量，Hex-T3 TM的自由基阳离子中还建议了对噻吩支之间的相互作用。

  DOI：

  10.1002/asia.201100639

文献信息

• 基于螺[芴-9,9`-氧杂蒽]的有机小分子空穴传输材料及其制备方法和应用
  申请人：南昌航空大学

  公开号：CN112250677A

  公开（公告）日：2021-01-22

  本发明公开了一种基于螺[芴‑9,9'‑氧杂蒽]的有机小分子空穴传输材料及其制备方法和应用，该有机小分子空穴传输材料以螺[芴‑9,9'‑氧杂蒽]为核，具有良好的无定形态和优异的溶解性能；侧链加以不同个数的噻吩基团，通过其高电子密度、优异的载流子传输能力、可控的光学及电化学性质等特点，赋予材料更加优秀的物理及光电性能；末端烷基链的修饰增加其溶解性，有利于材料的成膜性，更易于加工；同时通过简单的合成路线合成，并且原料易得，成本低廉；该有机小分子空穴传输材料应用于全无机钙钛矿太阳能电池，其电池效率相较于原始的电池效率为更高，说明其对提高全无机钙钛矿太阳能电池效率具有实际意义。
• Indenothiophene-based asymmetric small molecules for organic solar cells
  作者：Qi Shang、Meng Wang、Jiajun Wei、Qingdong Zheng

  DOI：10.1039/c7ra01902e

  日期：——

  development of organic semiconductors is of key importance in order to improve the performance of organic solar cells (OSCs). Three indenothiophene (IT)-containing small molecules (IT3T, ITFBT and IT2FBT) were designed and synthesized for small molecule OSCs. The thermal, optical, and electrochemical properties of the molecules were investigated. The optical bandgaps of the three small molecules are ranged

  为了改善有机太阳能电池（OSC）的性能，有机半导体的开发至关重要。设计并合成了三种含茚并噻吩（IT）的小分子（IT3T，ITFBT和IT2FBT）用于小分子OSC。研究了分子的热，光学和电化学性质。这三个小分子的光学带隙范围为1.80至2.20 eV，具体取决于IT侧翼的不同末端基团。我们通过用PC 71 BM作为电子受体制造OSC，研究了这三种分子的光伏性能。在三个分子中，ITFBF在0.98 V的高开路电压（V OC）下，其最佳功率转换效率为4.57％。我们还简要讨论了OSC所用小分子的结构性质准则。结果表明，基于IT的小分子有望用于具有大V OC的小分子OSC 。
• Synthesis of Monochlorosilyl Derivatives of Dialkyloligothiophenes for Self-Assembling Monolayer Field-Effect Transistors
  作者：Sergei A. Ponomarenko、Oleg V. Borshchev、Timo Meyer-Friedrichsen、Alexandra P. Pleshkova、Sepas Setayesh、Edsger C. P. Smits、Simon G. J. Mathijssen、Dago M. de Leeuw、Stephan Kirchmeyer、Aziz M. Muzafarov

  DOI：10.1021/om100139y

  日期：2010.10.11

  Unsymmetrical dimethylchlorosilyl-substituted alpha,alpha'-dialkylquater-, quinque-, and sexithiophenes were designed and successfully synthesized by a combination of Kumada and Suzuki cross-coupling reactions followed by hydrosilylation. Optimization possibilities of the hydrosilylation of low-soluble linear oligothiophenes by dimethylchlorosilane as well as the nonreactive byproducts formed are described. The molecular structures of the obtained dimethylchlorosilyl-functionalized oligothiophenes were proven by NMR and DCI MS techniques. These compounds were found to be stable and reactive enough, even in the presence of the nonreactive byproducts, to form semiconducting monolayers on dielectric hydroxylated SiO2 surfaces by self-assembly from solution. The semiconducting properties of these oligothiophene SAMs were as good as those of bulk oligothiophenes. This allowed the production of stable, even under ambient conditions, SAMFETs with a mobility of up to 0.04 cm(2)/(V s) and an on/off ratio up to 1 x 10(8).
• ORGANIC SEMICONDUCTOR MATERIAL AND ORGANIC FIELD EFFECT TRANSISTOR
  申请人：Ohba Yoshihiro

  公开号：US20090159876A1

  公开（公告）日：2009-06-25

  Disclosed is an adequately stable organic semiconductor material which can be used in a coating process while having high regularity and crystallinity. For obtaining such an organic semiconductor material, there is used a compound wherein 6-20 five-membered and/or six-membered aromatic rings are bound. This compound contains a partial structure represented by the formula (1) below, while having a mobility of not less than 1.0×10 −3 cm 2 /Vs and an ionization potential in the solid state of not less than 4.8 eV and not more than 5.6 eV. (1) In the formula, R 1 and R 2 independently represent a hydrogen atom or a monovalent organic group. In this connection, at least one of R 1 and R 2 is an optionally substituted aromatic group.