2,5-bis(trimethylstannyl)thieno[2,3-b]thiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 2,5-bis(trimethylstannyl)thieno[2,3-b]thiophene
• 英文别名: 2,5-Bis-trimethylstannyl-thieno[2,3-b]thiophene；trimethyl-(5-trimethylstannylthieno[2,3-b]thiophen-2-yl)stannane
• 化学式: C₁₂H₂₀S₂Sn₂
• 分子量: 465.843
• InChiKey: SCCVQQADUOTXQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-bis(trimethylstannyl)thieno[2,3-b]thiophene 、 2-溴-3-十二烷基噻吩 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 2,5-bis(3-dodecylthiophen-2-yl)thieno[2,3-b]thiophene
  参考文献：
  名称：

  Effects of Cross-Conjugation on the Optical Absorption and Frontier Orbital Levels of Donor–Acceptor Polymers

  摘要：

  The influence of cross-conjugation on the optical and electrochemical properties Of donor acceptor copolymers is investigated. Isoindigo, substituted at the 6,6' or the 5,5' positions, and thieno[3,2-b]thiopliene and thieno[2,3-]thiophene ate taken as conjugated and cross-conjugated electron-deficient and electron-rich building blocks from which four isomeric donor acceptor polymers were synthesized. Introducing cross-conjugation in isoindigo, has only a small effect on the electrochemical band gap and on the onset of the absorption, which remains in the near-infrared. The optical absorption spectra, however, differ strongly because cross-conjugation strongly reduces the absorption coefficient. DFT calculations confirm that the transition to the lowest excited singlet state has a small oscillator strength in cross-conjugated isoindigo model Compounds. Cross-conjugation in thienothiophene exerts a different effect. It causes a moderate but distinct blue-shift of the optical absorption and a deeper HOMO energy level.

  DOI：

  10.1021/acs.macromol.5b00046
• 作为产物：
  描述：

  噻吩[2,3-B]噻吩 、 三甲基氯化锡 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以43.5%的产率得到2,5-bis(trimethylstannyl)thieno[2,3-b]thiophene
  参考文献：
  名称：

  的diketopyrrolopyrrole-处理温度控制ALT -噻吩并[2,3- b ]噻吩的聚合物为高迁移率的薄膜晶体管和聚合物太阳能电池具有高的开路电压

  摘要：

  我们合成了基于二酮吡咯并吡咯（DPP）和噻吩并[2,3- b ]噻吩（TTi）的平面pDPPTTi-OD聚合物，并研究了pDPPTTi-OD聚合物的电性能。pDPPTTi-OD薄膜显示出1.57 eV的低光学带隙，HOMO和LUMO分别为-5.40和-3.74 eV。在有机薄膜晶体管（OTFT）器件中，经过150°C退火的pDPPTTi-OD膜显示出0.16 cm 2 V -1 s -1的高空穴迁移率。还测量了包含pDPPTTi-OD的聚合物太阳能电池（PSC）的光伏性能。pDPPTTi-OD：PC 71在25、70和90°C下旋涂BM共混膜。高温处理通过有效地减小PC 71 BM域的尺寸，显着提高了PSC的功率转换效率，从而改善了pDPPTTi-OD与PC 71 BM之间的互溶性。这项工作表明，TTi部分是OTFT和PSC中高性能D–A型聚合物的有用供体构件，并且应控制加工温度以充分实现材料的有益固有特性。

  DOI：

  10.1016/j.polymer.2016.10.024

文献信息

• Using bis(pinacolato)diboron to improve the quality of regioregular conjugated co-polymers
  作者：Frank Brouwer、Jan Alma、Hennie Valkenier、Thomas P. Voortman、Jorrit Hillebrand、Ryan C. Chiechi、Jan C. Hummelen

  DOI：10.1039/c0jm02359k

  日期：——

  We demonstrate the use of bis(pinacolato)diboron to directly polymerize symmetric, bisbromo, thiophene-based monomers via a Suzuki homo-polymerization to form co-polymers in less steps than the corresponding co-polymerization. We compare this method to the commonly used Stille co-polymerization by preparing four thiophene-based co-polymers using both methods. We use MALDI-TOF mass spectrometry to show that this new method produces high-quality, uniform polymers with narrow distributions of end-groups. By varying the electronegativity of the monomers, we demonstrate rudimentary control over these end-groups, forming either bis-H-, mono-H-mono-Br-, or bis-Br-terminated polymers in order of increasing electronegativity.

  我们展示了通过Suzuki同聚合反应，利用双(频哪醇基)二硼直接聚合对称、双溴、噻吩基单体，以较少步骤形成共聚物的方法。通过采用两种方法（新方法和常用的Stille共聚法）制备四种噻吩基共聚物，并将这种方法与Stille共聚法进行对比。通过MALDI-TOF质谱分析，我们证明这种方法能生成高质量、均一的聚合物，其端基分布狭窄。通过改变单体的电负性，我们初步实现了对这些端基的控制，按照电负性增加的顺序，分别形成双氢端基、单氢单溴端基或双溴端基的聚合物。
• Mono-, oligo-and polythieno[2,3-b]thiophenes
  申请人：Heeney Martin

  公开号：US20050090640A1

  公开（公告）日：2005-04-28

  The invention relates to novel mono-, oligo and poly[2,3-b]-thienothiophenes, their use as semiconductors or charge transport materials, in optical, electro-optical or electronic devices like for example liquid crystal displays, optical films, organic field effect transistors (FET or OFET) for thin film transistor liquid crystal displays and integrated circuit devices such as RFID tags, electroluminescent devices in flat panel displays, and in photovoltaic and sensor devices, and to a field effect transistor, light emitting device or ID tag comprising the novel polymers.

  本发明涉及新型单体、寡聚体和聚[2,3-b]-噻吩噻吩，它们可用作半导体或电荷传输材料，在光学、电光或电子器件中使用，例如液晶显示器、光学薄膜、用于薄膜晶体管液晶显示器和集成电路器件（如RFID标签）、平板显示器中的电致发光器件，以及光伏和传感器器件。本发明还涉及一种场效应晶体管、发光器件或ID标签，其中包含新型聚合物。
• Mono-, oligo- and polythieno[2,3-b]thiophenes
  申请人：Merck Patent Gesellschaft

  公开号：US07183418B2

  公开（公告）日：2007-02-27

  The invention relates to novel mono-, oligo and poly[2,3-b]-thienothiophenes, their use as semiconductors or charge transport materials, in optical, electro-optical or electronic devices like for example liquid crystal displays, optical films, organic field effect transistors (FET or OFET) for thin film transistor liquid crystal displays and integrated circuit devices such as RFID tags, electroluminescent devices in flat panel displays, and in photovoltaic and sensor devices, and to a field effect transistor, light emitting device or ID tag comprising the novel polymers.

  本发明涉及新型单体、寡聚体和多聚[2,3-b]-噻吩噻吩，它们作为半导体或电荷传输材料，在光学、电光或电子器件中使用，例如液晶显示器、光学薄膜、用于薄膜晶体管液晶显示器和集成电路器件（如RFID标签）、平板显示器中的电致发光器件，以及在光伏和传感器器件中使用，并且涉及一种场效应晶体管、发光器件或ID标签，其中包含新型聚合物。
• Mono-, Oligo- and Polythieno(2,3-b)thiophenes
  申请人：Merck Patent GmbH

  公开号：EP1510535B1

  公开（公告）日：2008-11-05