3,6-di(thiophen-2-yl)-2,5-bis(3,7,11-trimethyldodecyl)-3H,6H-pyrrolo[3,4-c]pyrrole-1,4-dione | 1309383-80-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,6-di(thiophen-2-yl)-2,5-bis(3,7,11-trimethyldodecyl)-3H,6H-pyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: 1,4-Dithiophen-2-yl-2,5-bis(3,7,11-trimethyldodecyl)pyrrolo[3,4-c]pyrrole-3,6-dione；1,4-dithiophen-2-yl-2,5-bis(3,7,11-trimethyldodecyl)pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1309383-80-9
• 化学式: C₄₄H₆₈N₂O₂S₂
• 分子量: 721.168
• InChiKey: SPKXVBYPGLWGPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  50
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  3,6-di(thiophen-2-yl)-2,5-bis(3,7,11-trimethyldodecyl)-3H,6H-pyrrolo[3,4-c]pyrrole-1,4-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 36.0h， 以63%的产率得到3,6-di(5-bromothiophen-2-yl)-2,5-bis(3,7,11-trimethyldodecyl)-3H,6H-pyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  Low-band gap copolymers of ethynylfluorene and 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione synthesized under microwave irradiation for polymer photovoltaic cells

  摘要：

  Copolymers with alternative electron-donating and electron-withdrawing units can exhibit a low-band gap and can be used as the donor materials in polymer photovoltaic cells (PVs). This paper reports the synthesis of copolymers of electron-donating ethynylfluorene and electron-withdrawing 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyyrole-1,4-dione (DPP) via the Pd-catalyzed Sonogashira coupling and their application in polymer PVs. Applying microwave irradiation during the Sonogashira coupling can shorten the polymerization time from several days to a couple of minutes and improve the molecular weight. These polymers have band gaps of about 1.85 eV. Their energy levels indicate that they can be used as the donor materials for polymer PVs. Polymer PVs were fabricated using these polymers as donors and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) as acceptor. Applying the microwave irradiation during the Sonogashira coupling can significantly improve the photovoltaic performance of the polymer PVs. Power conversion efficiency (PCE) of 2.25% was achieved on polymer PVs under AM 1.5G illumination (100 mW cm(-2)). (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2011.03.023
• 作为产物：
  描述：

  3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 、 3,7,11-trimethyl-1-dodecyl iodide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以67%的产率得到3,6-di(thiophen-2-yl)-2,5-bis(3,7,11-trimethyldodecyl)-3H,6H-pyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  Low-band gap copolymers of ethynylfluorene and 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione synthesized under microwave irradiation for polymer photovoltaic cells

  摘要：

  Copolymers with alternative electron-donating and electron-withdrawing units can exhibit a low-band gap and can be used as the donor materials in polymer photovoltaic cells (PVs). This paper reports the synthesis of copolymers of electron-donating ethynylfluorene and electron-withdrawing 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyyrole-1,4-dione (DPP) via the Pd-catalyzed Sonogashira coupling and their application in polymer PVs. Applying microwave irradiation during the Sonogashira coupling can shorten the polymerization time from several days to a couple of minutes and improve the molecular weight. These polymers have band gaps of about 1.85 eV. Their energy levels indicate that they can be used as the donor materials for polymer PVs. Polymer PVs were fabricated using these polymers as donors and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) as acceptor. Applying the microwave irradiation during the Sonogashira coupling can significantly improve the photovoltaic performance of the polymer PVs. Power conversion efficiency (PCE) of 2.25% was achieved on polymer PVs under AM 1.5G illumination (100 mW cm(-2)). (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2011.03.023

文献信息

• POLYMER COMPOUND AND ORGANIC PHOTOELECTRIC CONVERSION DEVICE
  申请人：Uetani Yasunori

  公开号：US20130200351A1

  公开（公告）日：2013-08-08

  A polymer compound comprising a repeating unit represented by the formula (1) is useful for an organic photoelectric conversion device: [wherein, Q, R and T are the same or different and represent a hydrogen atom, a fluorine atom, an alkyl group optionally substituted by a fluorine atom, an alkoxy group optionally substituted by a fluorine atom, an optionally substituted aryl group, an optionally substituted heteroaryl group or a group represented by the formula (2). Two Qs may be the same or different. Two Rs may be the same or different. Four Ts may be the same or different. (wherein, m1 represents an integer of 0 to 6 and m2 represents an integer of 0 to 6. R′ represents an alkyl group, an optionally substituted aryl group or an optionally substituted heteroaryl group.)].
• Low-band gap copolymers of ethynylfluorene and 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione synthesized under microwave irradiation for polymer photovoltaic cells
  作者：Zhonglian Wu、Benhu Fan、Aiyuan Li、Feng Xue、Jianyong Ouyang

  DOI：10.1016/j.orgel.2011.03.023

  日期：2011.6

  Copolymers with alternative electron-donating and electron-withdrawing units can exhibit a low-band gap and can be used as the donor materials in polymer photovoltaic cells (PVs). This paper reports the synthesis of copolymers of electron-donating ethynylfluorene and electron-withdrawing 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyyrole-1,4-dione (DPP) via the Pd-catalyzed Sonogashira coupling and their application in polymer PVs. Applying microwave irradiation during the Sonogashira coupling can shorten the polymerization time from several days to a couple of minutes and improve the molecular weight. These polymers have band gaps of about 1.85 eV. Their energy levels indicate that they can be used as the donor materials for polymer PVs. Polymer PVs were fabricated using these polymers as donors and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) as acceptor. Applying the microwave irradiation during the Sonogashira coupling can significantly improve the photovoltaic performance of the polymer PVs. Power conversion efficiency (PCE) of 2.25% was achieved on polymer PVs under AM 1.5G illumination (100 mW cm(-2)). (C) 2011 Elsevier B.V. All rights reserved.