5,5''-Dibromo-3',4'-dibutyl-2,2':5',2''-terthiophene | 349481-81-8

• 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: 5,5''-Dibromo-3',4'-dibutyl-2,2':5',2''-terthiophene
• 英文别名: 2,5-Bis(5-bromothiophen-2-yl)-3,4-dibutylthiophene
• CAS: 349481-81-8
• 化学式: C₂₀H₂₂Br₂S₃
• 分子量: 518.401
• InChiKey: AHQQVGWGIARRDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  5,5''-Dibromo-3',4'-dibutyl-2,2':5',2''-terthiophene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 镍 mercury(II) diacetate 、 碘 、 三乙胺 作用下， 以 吡啶 、 氯仿 为溶剂， 反应 14.0h， 生成 5,5'''-bis(trimethylsilylethynyl)-3,3'',3'''',4,4'',4''''-hexabutyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
  参考文献：
  名称：

  第一个全α-共轭大环低聚噻吩的合成：在纳米范围内具有可调腔的环[n]噻吩

  摘要：

  DOI：

  10.1002/1521-3773(20001002)39:19<3481::aid-anie3481>3.0.co;2-o
• 作为产物：
  描述：

  3,4-二丁基噻吩 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) N-溴代丁二酰亚胺(NBS) 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5,5''-Dibromo-3',4'-dibutyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Homologous series of regioregular alkylsubstituted oligothiophenes up to an 11-mer

  摘要：

  A complete series of structurally well-defined butylated oligothiophenes up to an Il-mer was synthesized by a combination of aryl-aryl cross-coupling reactions and cyclization of 1,3-butadiyne precursors with sulfide anions. Palladium-catalyzed cross-coupling of halogenated thiophene units with trimethylsilylacetylene effectively yields ethynylated thiophenes which after deprotection are oxidatively coupled to the corresponding 1,3-butadiynes. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00254-x

文献信息

• Molecular Junctions Composed of Oligothiophene Dithiol-Bridged Gold Nanoparticles Exhibiting Photoresponsive Properties
  作者：Wei Huang、Gou Masuda、Seisuke Maeda、Hirofumi Tanaka、Takuji Ogawa

  DOI：10.1002/chem.200500822

  日期：2006.1

  Three oligothiophene dithiols with different numbers of thiophene rings (3, 6 or 9) have been synthesized and characterized. The X-ray single crystal structures of terthiophene 2 and sexithiophene 5 are reported herein to show the exact molecular lengths, and to explain the difference between their UV-visible spectra arising from the different packing modes. These dithiols with different chain lengths

  合成并表征了具有不同数目的噻吩环（3、6或9）的三种低聚噻吩二硫醇。本文报道了对噻吩2和对噻吩5的X射线单晶结构，显示了确切的分子长度，并解释了由不同堆积模式引起的紫外可见光谱之间的差异。然后，在存在1微米间隙的Au电极的情况下，通过原位硫醇-硫醇配体交换，将这些具有不同链长的二硫醇用2-十二烷硫醇保护的活性金纳米颗粒（Au-NPs）处理。因此，制备了由自组装膜组成的分子结，其中寡噻吩二硫醇桥联的Au-NP通过Au-S键合触点连接到两个电极上。通过SEM和AFM方法研究了这些薄膜的形貌和电流-电压（IV）特性，这表明薄膜的厚度（3-4层）在一个孤立的Au-NP的尺寸内变化，并且典型地取决于距离可以观察到半导体性能。对这些分子连接进行了随温度变化的IV测量，其中薄膜在6-300 K的温度范围内用作活性元素。进行了经典的Arrhenius图和随后的线性拟合，以得出设备的激活能（deltaE）。此外，分别在80
• Dinitro and Quinodimethane Derivatives of Terthiophene That Can Be Both Oxidized and Reduced. Crystal Structures, Spectra, and a Method for Analyzing Quinoid Contributions to Structure
  作者：Ted M. Pappenfus、Jonathan D. Raff、Eric J. Hukkanen、Jason R. Burney、Juan Casado、Steven M. Drew、Larry L. Miller、Kent R. Mann

  DOI：10.1021/jo025572b

  日期：2002.8.1

  anion radical and dianion. The spectra of 2 and its three redox partners were analyzed in terms of a limiting structure in which the neutral 2 has orbitals corresponding to those of a substituted-terthiophene dication. Compound 1 crystallizes with the thiophene rings held in an unusual nonplanar, cisoid configuration in face-to-face pi-stacks, with a spacing between molecules of 3.65 A. The C-C bond lengths

  两个新的低聚噻吩，二硝基化合物3'，4'-二丁基-5,5''-二硝基-2,2'：5'，2'-对噻吩（1）和喹二甲烷3'，4'-二丁基- 5,5''-双（二氰基亚甲基）-5,5''-二氢-2,2'：5'，2''-对噻吩（2）已通过电化学，UV-vis-NIR-合成红外光谱，ESR和X射线晶体学。这些被设计为电子和空穴载流子的化合物具有氧化还原特性，这对于低聚噻吩是不寻常的。循环伏安法和光谱电化学表明，每种化合物均可被氧化成阳离子自由基，并被还原成阴离子自由基和二价阴离子。根据限制结构分析了2及其三个氧化还原配偶体的光谱，其中中性2的轨道对应于取代的对噻吩指示的轨道。化合物1结晶时，噻吩环在面对面的pi堆栈中以不寻常的非平面，类cisoid构型保持，分子之间的间距为3.65A。硝基取代的外环的CC键长具有quinoid特性。化合物2与噻吩环一起以平面，Transoid构型结晶。分子被固定在由p
• PROCESSES FOR PREPARING CURED FILMS, THE RESULTING FILMS, AND PLASMA-INITIATED POLYMERIZABLE COMPOSITIONS
  申请人：FUJIFILM Corporation

  公开号：US20140170405A1

  公开（公告）日：2014-06-19

  Provided are novel plasma-assisted processes for preparing cured films having excellent heat resistance and moisture resistance. A process for preparing a cured film, comprising at least: applying a composition containing (A) at least one conductive polymer precursor on a substrate to form a coating layer, and irradiating the coating layer with a plasma to polymerize the conductive polymer precursor (A).

  提供了一种新型等离子体辅助制备固化膜的工艺，该固化膜具有优异的耐热性和耐潮性。一种制备固化膜的工艺，包括至少以下步骤：在基板上涂布含有（A）至少一种导电聚合物前体的组合物以形成涂层层，然后用等离子体照射涂层层以聚合导电聚合物前体（A）。
• A π-Stacking Terthiophene-Based Quinodimethane Is an n-Channel Conductor in a Thin Film Transistor
  作者：Ted M. Pappenfus、Reid J. Chesterfield、C. Daniel Frisbie、Kent R. Mann、Juan Casado、Jonathan D. Raff、Larry L. Miller

  DOI：10.1021/ja025553j

  日期：2002.4.1

  A terthiophene-based quinodimethane, 3',4'-dibutyl-5,5' '-bis(dicyanomethylene)-5,5' '-dihydro-2,2':5',2' '-terthiophene (1) was synthesized and crystallized. Compound 1 has a planar quinoid geometry that is stabilized by dicyanomethylene groups at each end of the molecule. In the crystal each molecule is part of a dimerized face-to-face pi-stack, with intermolecular spacings of 3.47 and 3.63 A, respectively. Cyclic voltammetry showed that 1 could be reversibly reduced and oxidized in methylene chloride solution. Thin film transistors (TFTs) were prepared by vacuum evaporation of 1 onto SiO2(300 nm)/Si substrates, followed by evaporation of Ag source and drain contacts. The doped Si substrate served as the gate electrode. X-ray diffraction and atomic force microscopy indicate the films are polycrystalline, with the long axes of the molecules approximately perpendicular to the substrate. The TFT measurements revealed n-channel conduction in films of 1, with room-temperature electron field effect mobilities as high as 0.005 cm2/Vs. The butyl side chains give 1 appreciable solubility in a range of common solvents, and preliminary TFT results on films cast from chlorobenzene show electron mobility as high as 0.002 cm2/Vs. These results indicate that pi-stacked quinoidal thiophene oligomers are a promising new class of soluble n-channel organic semiconductors.