5,5''-dibromo-3'-methyl-[2,2',5',2'']-terthiophene | 863208-08-6

• 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'-methyl-[2,2',5',2'']-terthiophene
• 英文别名: 5,5"-dibromo-3'-methyl-[2,2',5',2"]terthiophene；2,5-Bis(5-bromothiophen-2-yl)-3-methylthiophene
• CAS: 863208-08-6
• 化学式: C₁₃H₈Br₂S₃
• 分子量: 420.213
• InChiKey: DYOFPJOESYDLBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  18
• 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：

  5,5''-dibromo-3'-methyl-[2,2',5',2'']-terthiophene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成 5,5''-dibromo-3'-bromomethyl-[2,2',5',2'']-terthiophene
  参考文献：
  名称：

  Conjugated Side-Chain Isolated Polythiophene: Synthesis and Photovoltaic Application

  摘要：

  A design concept of "side chain isolation" was proposed for developing new polythiophene derivatives with conjugated side chain (CSC-PTs), and PTSTPA with styryl triphenylamine (TPA) side chain and unsubstituted tetrathienyl spacer was designed and synthesized. Compared to previously reported CSC-PTs, side chain isolated PT5TPA showed red shifted and enhanced pi-pi* transition absorption of the polymer backbone along with the shoulder peak and steep absorption edge, indicating improved planarity of the backbone. In addition, the unsubstituted thiophene spacer along the polymer backbone of the side chain isolated PTSTPA results in a lower HOMO energy level of the polymer at 5.1 eV. The polymer solar cell based on PT5TPA as donor and indene-C-60 bisadduct as acceptor displayed a power conversion efficiency of 3.6% with a high open circuit voltage of 0.94 V, under the illumination of AM1.5G, 100 mW/cm(2). The results indicate that the side chain isolated CSC-PTs could open a new way for developing high performance photovoltaic polymers.

  DOI：

  10.1021/ma201718x
• 作为产物：
  描述：

  3'-methyl-2,2':5',2''-terthienyl 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以85%的产率得到5,5''-dibromo-3'-methyl-[2,2',5',2'']-terthiophene
  参考文献：
  名称：

  Conjugated Side-Chain Isolated Polythiophene: Synthesis and Photovoltaic Application

  摘要：

  A design concept of "side chain isolation" was proposed for developing new polythiophene derivatives with conjugated side chain (CSC-PTs), and PTSTPA with styryl triphenylamine (TPA) side chain and unsubstituted tetrathienyl spacer was designed and synthesized. Compared to previously reported CSC-PTs, side chain isolated PT5TPA showed red shifted and enhanced pi-pi* transition absorption of the polymer backbone along with the shoulder peak and steep absorption edge, indicating improved planarity of the backbone. In addition, the unsubstituted thiophene spacer along the polymer backbone of the side chain isolated PTSTPA results in a lower HOMO energy level of the polymer at 5.1 eV. The polymer solar cell based on PT5TPA as donor and indene-C-60 bisadduct as acceptor displayed a power conversion efficiency of 3.6% with a high open circuit voltage of 0.94 V, under the illumination of AM1.5G, 100 mW/cm(2). The results indicate that the side chain isolated CSC-PTs could open a new way for developing high performance photovoltaic polymers.

  DOI：

  10.1021/ma201718x

文献信息

• Reactive mesogenic charge transport compounds
  申请人：Heeney Martin

  公开号：US20050184274A1

  公开（公告）日：2005-08-25

  The invention relates to new reactive mesogenic compounds with charge transport properties comprising at least two thiophene groups, 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 reactive mesogenic charge transport compounds.

  本发明涉及一种新的具有电荷传输性质的反应性介向化合物，包括至少两个噻吩基团，其用作半导体或电荷传输材料，用于光学、电光或电子设备，例如液晶显示器、光学薄膜、有机场效应晶体管（FET或OFET）用于薄膜晶体管液晶显示器和集成电路器件，例如RFID标签、平面显示器中的电致发光器件以及光伏和传感器器件，以及包括反应性介向电荷传输化合物的场效应晶体管、发光器件或ID标签。
• Reactive mesogenic charge transport compounds containing at least two thiophene groups
  申请人：Merck Patent GmbH

  公开号：EP1903036A1

  公开（公告）日：2008-03-26

  The invention relates to new reactive mesogenic compounds with charge transport properties comprising at least two thiophene groups, their use as semiconductors or charge transport materials, in optical, electro-optical or electronic devices like for example liquid crystal displays, opiicai 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 reactive mesogenic charge transport compounds.

  本发明涉及至少含有两个噻吩基团的具有电荷传输特性的新型活性介源化合物，它们可用作光学、电子光学或电子设备中的半导体或电荷传输材料，例如液晶显示器、鸦片胶片、用于薄膜晶体管液晶显示器和集成电路设备（如 RFID 标签）的有机场效应晶体管（FET 或 OFET）、平板显示器中的电致发光器件以及光电器件、用于薄膜晶体管液晶显示器和集成电路设备（如 RFID 标签）的有机场效应晶体管 （FET 或 OFET）、平板显示器中的电致发光器件、光电和传感器设备，以及包含活性介源电荷传输化合物 的场效应晶体管、发光器件或 ID 标签。
• [EN] REACTIVE MESOGENIC CHARGE TRANSPORT COMPOUNDS CONTAINING AT LEAST TWO THIOPHENE GROUPS<br/>[FR] COMPOSES MESOGENES REACTIFS A PROPRIETES DE TRANSPORT DE CHARGE
  申请人：MERCK PATENT GMBH

  公开号：WO2005080369A3

  公开（公告）日：2005-10-06
• REACTIVE MESOGENIC CHARGE TRANSPORT COMPOUNDS CONTAINING AT LEAST TWO THIOPHENE GROUPS
  申请人：Merck Patent GmbH

  公开号：EP1725541A2

  公开（公告）日：2006-11-29
• US7674397B2
  申请人：——

  公开号：US7674397B2

  公开（公告）日：2010-03-09