5''-Bromo-5-methyl-[2,2',5',2'']terthiophene | 351066-58-5

• 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-methyl-[2,2',5',2'']terthiophene
• 英文别名: 2-Bromo-5-[5-(5-methylthiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 351066-58-5
• 化学式: C₁₃H₉BrS₃
• 分子量: 341.316
• InChiKey: CHKGEYAQIVPFIX-UHFFFAOYSA-N

物化性质

• 沸点：
  393.0±37.0 °C(Predicted)
• 密度：
  1.545±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 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-methyl-[2,2',5',2'']terthiophene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 5-vinyl-5''-methyl-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：

  5-iodo-2,2'-bithiophene 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 31.5h， 生成 5''-Bromo-5-methyl-[2,2',5',2'']terthiophene
  参考文献：
  名称：

  Synthesis of Thiophene-Based Building Blocks via Facile α-Monoiodination

  摘要：

  描述了一种选择性α-单碘化对称噻吩封闭片段的新程序。单碘化衍生物进一步被修饰，获得了一系列基于噻吩的构建块，这些构建块可用于通过片段耦合合成 oligomer。

  DOI：

  10.1055/s-2001-13361

文献信息

• Preparation of a New Spirobi[thieno[2,3-c]pyran] and Its Selective Mono- and Dimetalation: Application for the Preparation of Soluble Conjugated Oligothiophenes and Pyrene Derivatives
  作者：Paul Knochel、Vasudevan Dhayalan、Fernando Alcañiz、Veronika Werner、Konstantin Karaghiosoff

  DOI：10.1055/s-0035-1560187

  日期：——

  Abstract 3-Thienylacetic acid was converted in six steps into a new spirobi[thieno[2,3-c]pyran] (overall yield: 52%). The spirobi[thieno[2,3-c]pyran] was selectively mono- or dimetalated with butyllithium and then transmetalated with zinc chloride; cross-coupling reaction with various aryl or heteroaryl bromides, including bromo-oligothiophenes, acid chlorides, and 1-bromopyrene, produced the corresponding

  摘要 3-噻吩乙酸经六个步骤转化为新的螺双[thieno [2,3- c ] pyran ]（总收率：52％）。将螺双[thieno [2,3- c ] pyran]用丁基锂选择性地单金属化或双金属化，然后用氯化锌金属化；与各种芳基或杂芳基溴化物（包括溴-低聚噻吩，酰氯和1-溴py）的交叉偶联反应可高产率产生相应的螺衍生物。 3-噻吩乙酸经六个步骤转化为新的螺双[thieno [2,3- c ] pyran ]（总收率：52％）。将螺双[thieno [2,3- c ] pyran]用丁基锂选择性地单金属化或双金属化，然后用氯化锌金属化；与各种芳基或杂芳基溴化物（包括溴-低聚噻吩，酰氯和1-溴py）的交叉偶联反应可高产率产生相应的螺衍生物。
• Steric Control in the π-Dimerization of Oligothiophene Radical Cations Annelated with Bicyclo[2.2.2]octene Units
  作者：Masaki Tateno、Masayoshi Takase、Masahiko Iyoda、Koichi Komatsu、Tohru Nishinaga

  DOI：10.1002/chem.201204332

  日期：2013.4.22

  through chemical one‐electron oxidation by using nitrosonium hexafluoroantimonate. From variable‐temperature electron spin resonance and electronic absorption measurements, the π‐dimerization capability was found to vary among the members of the 2(nT)+.SbF6− series and 3+.SbF6− series of compounds. To examine these results, density functional theory (DFT) calculations at the M06‐2X/6‐31G(d) level were conducted

  甲两个系列低聚噻吩2（Ñ T）（Ñ = 4,5）中，用双环[2.2.2]辛烯（BCO）单元在两端稠合，和quaterthiophenes 3 - ç，与的BCO单位各种数目稠合合成了不同的位置，以研究π-二聚化的驱动力以及寡聚噻吩自由基阳离子的π-二聚体的结构-性质关系。它们的自由基阳离子盐是通过使用六氟锑酸硝鎓进行化学单电子氧化而制备的。从温度可变的电子自旋共振和电子吸收测量结果中，发现二聚能力在2（n T）的成员之间有所不同。+ 。的SbF 6 -系列和3 + 。的SbF 6 -系列化合物。为了检验这些结果，对M型二聚体进行了M06-2X / 6-31G（d）级的密度泛函理论（DFT）计算。发现该理论水平可成功复制先前报道的（2（3T））2 2+的X射线结构，该结构具有弯曲的π二聚体结构，具有顺式–顺式构象。通过随时间变化的DFT计算获得的二聚体吸收带与实验光谱合理吻合。π二聚体的吸引
• System for Controlling the Reactivity of Boronic Acids
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20130296573A1

  公开（公告）日：2013-11-07

  A protected organoboronic acid includes a boron having an sp 3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sp 3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.

  一种受保护的有机硼酸，其中包括一个具有sp3杂化的硼，一个构象刚性的保护基与硼键合，以及通过硼-碳键与硼键合的有机基。一种化学反应的方法包括将受保护的有机硼酸与试剂接触，所述受保护的有机硼酸包括一个具有sp3杂化的硼，一个构象刚性的保护基与硼键合，以及通过硼-碳键与硼键合的有机基。有机基被化学转化，而硼没有被化学转化。
• NOVEL HETEROCYCLIC FLUORESCENT DYES AND METHOD OF PRODUCTION THEREOF
  申请人：BASF SE

  公开号：US20150380660A1

  公开（公告）日：2015-12-31

  The invention relates to novel compounds of formula (III) that can be used as heterocyclic dyes of unique structure and properties. These compounds can be obtained in a three-step synthesis from simple substrates. The compounds according to the invention have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the compounds according to the invention are used in organic field effect transistors, organic photovoltaics (solar cells) and photodiodes.

  本发明涉及一种新型化合物(III)的配方，可用作具有独特结构和性质的杂环染料。这些化合物可以从简单的底物中通过三步合成得到。本发明中的化合物在有机溶剂中具有优异的溶解性和优异的膜形成性能。此外，当本发明中的化合物用于有机场效应晶体管、有机光伏(太阳能电池)和光电二极管时，可以观察到高能量转换效率、优异的场效应迁移率、良好的开/关电流比和/或优异的稳定性。
• 3D-Hybrid Networks with Controllable Electrical Conductivity from the Electrochemical Deposition of Terthiophene-Functionalized Polyphenylene Dendrimers
  作者：Hermann John、Roland Bauer、Pamela Espindola、Prashant Sonar、Jürgen Heinze、Klaus Müllen

  DOI：10.1002/anie.200462378

  日期：2005.4.15