2,2'-dibromo-4,4'-bis(2-ethylhexyl)[6,6'-bithieno[3,2,b]pyrrolylidene]-5,5'(4H,4H')-dione | 1147124-49-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,2'-dibromo-4,4'-bis(2-ethylhexyl)[6,6'-bithieno[3,2,b]pyrrolylidene]-5,5'(4H,4H')-dione
• 英文别名: 2-Bromo-6-[2-bromo-4-(2-ethylhexyl)-5-oxothieno[3,2-b]pyrrol-6-ylidene]-4-(2-ethylhexyl)thieno[3,2-b]pyrrol-5-one；2-bromo-6-[2-bromo-4-(2-ethylhexyl)-5-oxothieno[3,2-b]pyrrol-6-ylidene]-4-(2-ethylhexyl)thieno[3,2-b]pyrrol-5-one
• CAS: 1147124-49-9
• 化学式: C₂₈H₃₆Br₂N₂O₂S₂
• 分子量: 656.546
• InChiKey: SUOUFPMSMVABNV-UHFFFAOYSA-N

物化性质

• 沸点：
  639.7±55.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-dibromo-4,4'-bis(2-ethylhexyl)[6,6'-bithieno[3,2,b]pyrrolylidene]-5,5'(4H,4H')-dione 、 9-(4-乙炔苯基)咔唑 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 甲苯 为溶剂， 以54%的产率得到
  参考文献：
  名称：

  Solution-processable thienoisoindigo-based molecular donors for organic solar cells with high open-circuit voltage

  摘要：

  Two acetylene-bridged Donor Acceptor Donor (D-A-D) type small pi-conjugated molecules involving triphenylamine or N-phenylcarbazole as donor blocks (D) and thienoisoindigo as the acceptor unit (A) were synthesized and characterized by UV-Vis absorption and cyclic voltammetry. These donor materials were mixed with [6,6]-phenyl-C-61-butyric acid methyl ester to prepare bulk heterojunction solar cells by simple solution processing. Due to their low-lying highest occupied molecular orbital energy levels, high open-circuit voltages up to 0.99 V were measured. The triphenylamine end-capped derivative led to the best power conversion efficiency of ca 2.20%, which ranks among the highest reported value for thienoisoindigo-based materials. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.12.004
• 作为产物：
  描述：

  4-(2-Ethylhexyl)-6-[4-(2-ethylhexyl)-5-oxothieno[3,2-b]pyrrol-6-ylidene]thieno[3,2-b]pyrrol-5-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以87%的产率得到2,2'-dibromo-4,4'-bis(2-ethylhexyl)[6,6'-bithieno[3,2,b]pyrrolylidene]-5,5'(4H,4H')-dione
  参考文献：
  名称：

  KETOPYRROLES AS ORGANIC SEMICONDUCTORS

  摘要：

  单体或聚合物化合物至少包含式(Ia)中的一个基团，其中X为CR，其中R为H或按照权利要求1中定义的取代基，或为另一个酮吡咯基团，例如式(1b)或(1c)，其中此基团和所有其他符号如权利要求1所定义，显示出在有机溶剂中良好的溶解性和优异的成膜性能。此外，当根据本发明的聚合物用于半导体器件或有机光伏（PV）器件（太阳能电池）时，可以观察到高效的能量转换、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。

  公开号：

  US20100297405A1

文献信息

• Solution-processable thienoisoindigo-based molecular donors for organic solar cells with high open-circuit voltage
  作者：Oleh Vybornyi、Yue Jiang、François Baert、Dora Demeter、Jean Roncali、Philippe Blanchard、Clément Cabanetos

  DOI：10.1016/j.dyepig.2014.12.004

  日期：2015.4

  Two acetylene-bridged Donor Acceptor Donor (D-A-D) type small pi-conjugated molecules involving triphenylamine or N-phenylcarbazole as donor blocks (D) and thienoisoindigo as the acceptor unit (A) were synthesized and characterized by UV-Vis absorption and cyclic voltammetry. These donor materials were mixed with [6,6]-phenyl-C-61-butyric acid methyl ester to prepare bulk heterojunction solar cells by simple solution processing. Due to their low-lying highest occupied molecular orbital energy levels, high open-circuit voltages up to 0.99 V were measured. The triphenylamine end-capped derivative led to the best power conversion efficiency of ca 2.20%, which ranks among the highest reported value for thienoisoindigo-based materials. (C) 2014 Elsevier Ltd. All rights reserved.
• KETOPYRROLES AS ORGANIC SEMICONDUCTORS
  申请人：Flores Jean-Charles

  公开号：US20100297405A1

  公开（公告）日：2010-11-25

  Monomeric or polymeric compounds comprising at least one moiety of the formula (Ia) wherein X is CR, where R is H or a substituent as defined in claim 1, or is another ketopyrrole moiety e.g. of the formula (1 b ) or (1 c ) with this moiety and all other symbols are as defined in claim 1, show good 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 polymers according to the invention are used in semiconductor devices or organic photovoltaic (PV) devices (solar cells).

  单体或聚合物化合物至少包含式(Ia)中的一个基团，其中X为CR，其中R为H或按照权利要求1中定义的取代基，或为另一个酮吡咯基团，例如式(1b)或(1c)，其中此基团和所有其他符号如权利要求1所定义，显示出在有机溶剂中良好的溶解性和优异的成膜性能。此外，当根据本发明的聚合物用于半导体器件或有机光伏（PV）器件（太阳能电池）时，可以观察到高效的能量转换、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。