2-chloro-5-[5-(thiophen-2-yl)thiophen-2-yl]thiophene | 13669-15-3

• 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: 2-chloro-5-[5-(thiophen-2-yl)thiophen-2-yl]thiophene
• 英文别名: 2-chloro-2,2',5',2"-terthiophene；2-Chloro-5-(5-thiophen-2-ylthiophen-2-yl)thiophene
• CAS: 13669-15-3
• 化学式: C₁₂H₇ClS₃
• 分子量: 282.839
• InChiKey: INLKOWSRCJBIQA-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C
• 沸点：
  382.5±37.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴噻吩 、 2-chloro-3-methyl-5-(thiophen-2-yl)thiophene 在 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 、 Pd-PEPPSI-SIPr 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以91%的产率得到2-chloro-5-[5-(thiophen-2-yl)thiophen-2-yl]thiophene
  参考文献：
  名称：

  钯催化的氯噻吩去质子偶联反应制备氯官能化的噻吩低聚物的高效途径

  摘要：

  专用于Tamejiro桧山修教授在他的70之际个生日 抽象的 通过使用大体积的酰胺2,2,6,6-四甲基哌啶-1-基氯化镁氯化锂盐（TMPMgCl·LiCl），在噻吩环的5位上2-氯-3-取代的噻吩进行去质子金属化）。所获得的金属物质与溴噻吩反应，生成区域规则的头到尾型氯联噻吩，并通过与C–Cl键的偶联反应进行进一步的末端官能化。取代的氯联噻吩衍生物的去质子化C–H偶联缩聚得到的聚噻吩为正式的交替共聚物。 通过使用大体积的酰胺2,2,6,6-四甲基哌啶-1-基氯化镁氯化锂盐（TMPMgCl·LiCl），在噻吩环的5位上2-氯-3-取代的噻吩进行去质子金属化）。所获得的金属物质与溴噻吩反应，生成区域规则的头到尾型氯联噻吩，并通过与C–Cl键的偶联反应进行进一步的末端官能化。取代的氯联噻吩衍生物的去质子化C–H偶联缩聚得到的聚噻吩为正式的交替共聚物。

  DOI：

  10.1055/s-0036-1588094

文献信息

• Organic compound having functional groups different in elimination reactivity at both terminals, organic thin film, organic device and method of producing the same
  申请人：Imada Hiroshi

  公开号：US20070195576A1

  公开（公告）日：2007-08-23

  Provided are a single monomolecular film uniform in film thickness and highly ordered in molecule alignment and its multilayer film, an organic compound allowing production of such films at high reproducibility, an organic device superior in electroconductive properties and a method of producing the same. An organic compound represented by Formula: Si(A 1 )(A 2 )(A 3 )-B—Si(A 4 )(A 5 )(A 6 ) (A 1 to A 6 each represent a hydrogen atom, a halogen atom, an alkoxy group or an alkyl group and satisfy the relationship in elimination reactivity of: A 1 to A 3 >A 4 to A 6 ; and B represents a bivalent organic group), an organic thin film using the compound, and an organic device having the thin film; A method of producing an organic thin film and organic device, comprising a step of forming a single monomolecular film by allowing the silyl group having A 1 to A 3 in the organic compound to react with the substrate surface; a step of removing unreacted organic compounds by using a non-aqueous solvent; and a step of forming an additional monomolecular film of the organic compound by using the unreacted silyl groups present on the film surface side of the monomolecular film obtained as the sites for adsorption reaction.

  提供了一种在薄膜厚度上均匀且分子排列高度有序的单分子膜以及其多层膜，一种有机化合物可在高可重复性下制备这种膜，一种优越于导电性能的有机器件以及其生产方法。一种由化学式表示的有机化合物：Si(A1)(A2)(A3)-B—Si(A4)(A5)(A6)（其中A1到A6分别表示氢原子、卤素原子、烷氧基或烷基，并满足消除反应性的关系：A1到A3>A4到A6；B表示二价有机基），使用该化合物的有机薄膜，以及具有该薄膜的有机器件；一种制备有机薄膜和有机器件的方法，包括以下步骤：通过使具有A1到A3的硅基团与基底表面反应形成单分子膜；使用非水溶剂去除未反应的有机化合物；通过利用单分子膜表面上存在的未反应硅基团作为吸附反应位点形成有机化合物的额外单分子膜。
• Electron-Conjugated Organic Silane Compound and Production Method Thereof
  申请人：Nakagawa Masatoshi

  公开号：US20090005557A1

  公开（公告）日：2009-01-01

  The present invention provides a π-electron-conjugated organice silane compound that give an organic thin film superior in peeling restance, orientation, crystallinity and eletroconductive properties, and a production method thereof. A π-electron-conjugated organice silane compound represented by General Formula: R 1 -SiX 1 X 2 X 3 (R 1 represents an organic group having a particular monocyclic heterocyclic unit; and X 1 to X 3 are a group giving a hydroxyl group by hydrolysis). A method of producing the organic silane compound, comprising allowing a compound represented by General Formula: R 1 -Li (R 1 is the same as above) or a compound represented by General Formula: R 1 -MgX 5 (R 1 is the same as above; and X 5 represents a halogen atom) with a compound represented by General Formula: X 4 -SiX 1 X 2 X 3 (X 1 to X 3 are the same as above; and X 4 represents a hydrogen or halogen atom or a lower alkoxy group). A π-electron-conjugated organic silane compound represented by General Formula; Z-(R 11 ) m -SiR 12 R 13 R 14 (Z represents a organice group derived froma particular fused polycyclic heterocyclic compound; R 11 represents a bivalent organic group; m is 0 to 10; and R 12 to R 14 represents a halogen atom or an alkoxy group). A method of producing the organic silane compound, comprising allowing a compound represented by General Formula: Z-(R 11 ) m -MgX 30 (Z, R 11 and m are the same as above; and X 30 represents a halogen atom) to react with a compound represented by General Formula: X 31 -SiR 12 R 13 R 14 (X 31 represents a hydrogen or halogen atom or an alkoxy group; and R 12 to R 14 are the same as above).

  本发明提供了一种π-电子共轭有机硅烷化合物，使得有机薄膜在剥离抗性、取向性、结晶度和电导性能方面优越，并提供了其生产方法。一种由通用公式表示的π-电子共轭有机硅烷化合物：R1-SiX1X2X3（其中R1代表具有特定单环杂环单元的有机基；X1到X3是通过水解给出羟基的基团）。生产该有机硅烷化合物的方法，包括使由通用公式表示的化合物：R1-Li（R1与上述相同）或由通用公式表示的化合物：R1-MgX5（R1与上述相同；X5代表卤素原子）与由通用公式表示的化合物反应：X4-SiX1X2X3（X1到X3与上述相同；X4代表氢或卤素原子或较低的烷氧基）。由通用公式表示的π-电子共轭有机硅烷化合物；Z-(R11)m-SiR12R13R14（Z代表源自特定融合多环杂环化合物的有机基；R11代表二价有机基；m为0到10；R12到R14代表卤素原子或烷氧基）。生产该有机硅烷化合物的方法，包括使由通用公式表示的化合物：Z-(R11)m-MgX30（Z、R11和m与上述相同；X30代表卤素原子）与由通用公式表示的化合物反应：X31-SiR12R13R14（X31代表氢或卤素原子或烷氧基；R12到R14与上述相同）。
• Silicon Compound Containi-Electron Conjugated-System Molecule and Process for Producing the Same
  申请人：Nakagawa Masatoshi

  公开号：US20070287848A1

  公开（公告）日：2007-12-13

  A π-electron conjugate molecule-containing silicon compound represented by the formula (I): wherein R1 represents an organic group obtained by combining two or more units constituting plural π-electron conjugate systems, R2 represents a hydrophobic group and X1 to X3, which may be the same or different, respectively represent a group providing a hydroxyl group when it is hydrolyzed or a hydrogen atom.

  一种含有π-电子共轭分子的硅化合物，其化学式表示为(I)：其中，R1代表由构成多个π-电子共轭系统的两个或更多单元组合而成的有机基团，R2代表疏水基团，X1至X3分别可以相同或不同，代表在水解时提供羟基的基团或氢原子。
• Electron-Conjugated Organic Silane Compound, Functional Organic Thin Film And Production Method Thereof
  申请人：Imada Hiroshi

  公开号：US20080075950A1

  公开（公告）日：2008-03-27

  The present invention provides a highly orientated (crystallized) and highly-densely packed functional organic thin film that can be formed in a simple production method by solution method and adsorb tightly to a surface of a substrate, an organic silane compound for preparation of the thin film, and methods of preparing the same. An organic silane compound represented by General Formula; A-B—C—SiX 1 X 2 X 3 (wherein, A represents a monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms; B represents an oxygen or sulfur atom; C represents a π-electron-conjugated bivalent organic group; and each of X 1 to X 3 represents a group giving a hydroxyl group by hydrolysis). A functional organic thin film obtained by using the organic silane compound. A method of producing the organic silane compound, comprising introducing an aliphatic hydrocarbon group A onto a compound represented by General Formula; H—C—H (wherein, C is the same as above) via an ether or thioether bond in Williamson reaction, and additionally introducing a silyl group in reaction thereof with a compound represented by General Formula; X 4 —SiX 1 X 2 X 3 (wherein, X 1 to X 3 are the same as above). A method of producing the functional organic thin film, comprising forming a unimolecular film directly adsorbed on a substrate by hydrolyzing the silyl group in the organic silane compound and allowing the hydrolysate to react with the substrate surface, and washing and removing the unreacted organic silane compound on the unimolecular film with a nonaqueous organic solvent.

  本发明提供了一种高度定向（结晶）和高密度堆积的功能性有机薄膜，该薄膜可以通过溶液法简单制备，并紧密吸附在基底表面上，以及用于制备该薄膜的有机硅化合物和制备方法。有机硅化合物的通用式为：A-B—C—SiX1X2X3（其中，A表示具有1至30个碳原子的一价脂肪烃基；B表示氧或硫原子；C表示π-电子共轭的二价有机基团；X1至X3中的每一个表示通过水解给出羟基的基团）。使用有机硅化合物获得的功能性有机薄膜。制备有机硅化合物的方法包括通过Williamson反应在通用式为H—C—H（其中，C与上述相同）的化合物上引入脂肪烃基A，通过与通用式为X4—SiX1X2X3（其中，X1至X3与上述相同）的化合物反应，进一步引入硅基团。制备功能性有机薄膜的方法包括通过水解有机硅化合物中的硅基团，并使水解物与基底表面反应，从而直接在基底上形成单分子膜，并使用非水有机溶剂清洗和去除单分子膜上未反应的有机硅化合物。
• Rapid and Effective Multihalogenations of 2,2',5',2''-Terthiophene with 2-Halo-4,5-dichloropyridazin-3(2H)-ones under Ambient Conditions
  作者：Eun-Jung Kim、Kwang-Ju Jung、In-Hye Lee、Bo-Ram Kim、Jeum-Jong Kim、Jong-Keun Park、Sang-Gyeong Lee、Yong-Jin Yoon

  DOI：10.5012/bkcs.2010.31.10.2985

  日期：2010.10.20