3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione | 927896-66-0

• 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: 3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione
• 英文别名: 1,4-bis(5-thiophen-2-ylthiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 927896-66-0
• 化学式: C₂₂H₁₂N₂O₂S₄
• 分子量: 464.613
• InChiKey: DNMMDKCXZYZPAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  171
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  di-tert-butyl-3,6-di(2,2′-bithiophen-5-yl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5-(1H,4H)-dicarboxylate 以 neat (no solvent, solid phase) 为溶剂， 反应 48.0h， 生成 3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione
  参考文献：
  名称：

  Influence of Solubilizing Group Removal Rate on the Morphology and Crystallinity of a Diketopyrrolopyrrole-Based Compound

  摘要：

  Thermally cleavable solubilizing groups have been introduced on a pi-conjugated core, which can be cleaved and volatilized via heat treatment directly after the thin film fabrication. The X-ray and atomic force microscopic investigations of "3,6-di(2,2'-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione" (DPP-4T) synthesized from its precursor (di-tert-butyl-3,6-di(2,2'-bithiophen-5-yl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5-(1H,4H)-dicarboxylate) through thermal conversion reveals that the solubilizing group removal rate plays a crucial role on the ultimate grain size and crystallinity of the final compound (DPP-4T). This means that, when the heating rate is decreased from 50 to 0.1 degrees C/min, the crystallinity of DPP-4T powder decreases from 49% to 34%, and the grain size of DPP-4T film reduces from 976 to 344 nm. The crystallite size of the films can be further reduced to 185 nm by decarboxylating the films isothermally at 120 degrees C. The Fourier transform infrared spectra reveals that the reduction of crystallinity with the heating rate could be attributed to the trapping of gaseous byproducts inside the lattice, during the decarboxylation of the solubilizing group. The increment in intermolecular N-H center dot center dot center dot O=C hydrogen bond length together with the trapped gaseous byproducts results in a blue shift in the UV-vis absorption spectra while decreasing the heating rate as well as the isothermal decarboxylation temperature.

  DOI：

  10.1021/cg401625p

文献信息

• DIKETOPYRROLOPYRROLE POLYMERS FOR USE IN ORGANIC FIELD EFFECT TRANSISTORS
  申请人：BASF SE

  公开号：EP3456756A2

  公开（公告）日：2019-03-20

  The present invention relates to a process of producing polymers of formula VII, polymers comprising a repeating unit of the formula II and their use as organic semiconductor in organic devices, especially an organic field effect transistor (OFET), or a device containing a diode and/or an organic field effect transistor. The polymers according to the invention have excellent 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 organic field effect transistors.

  本发明涉及一种生产式 VII 聚合物、包含式 II 重复单元的聚合物的工艺，以及它们 在有机器件，特别是有机场效应晶体管（OFET）或包含二极管和/或有机场效应晶体管的器 件中作为有机半导体的用途。本发明的聚合物在有机溶剂中具有极佳的溶解性和优异的成膜性能。此外，在有机场效应晶体管中使用本发明的聚合物时，可以观察到较高的能量转换效率、出色的场效应迁移率、良好的开/关电流比和/或出色的稳定性。
• Diketopyrrolopyrrole polymers for use in organic field effect transistors
  申请人：BASF SE

  公开号：US10224484B2

  公开（公告）日：2019-03-05

  The present invention relates to polymers comprising a repeating unit of the formula I, or III and their use as organic semiconductor in organic devices, especially an organic field effect transistor (OFET), or a device containing a diode and/or an organic field effect transistor. The polymers according to the invention have excellent 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 organic field effect transistors.

  本发明涉及包含式 I 或式 III 重复单元的聚合物及其在有机器件中作为有机半导体的 用途，特别是有机场效应晶体管（OFET）或包含二极管和/或有机场效应晶体管的器件。本发明的聚合物在有机溶剂中具有极佳的溶解性和出色的成膜性能。此外，在有机场效应晶体管中使用本发明的聚合物时，可以观察到较高的能量转换效率、出色的场效应迁移率、良好的开/关电流比和/或出色的稳定性。
• PYRROLOPYRROLE DERIVATIVES, THEIR MANUFACTURE AND USE
  申请人：BASF SE

  公开号：EP2209788B1

  公开（公告）日：2013-09-04
• DIKETOPYRROLOPYRROLE POLYMERS FOR USE IN ORGANIC SEMICONDUCTOR DEVICES
  申请人：Düggeli Mathias

  公开号：US20110215313A1

  公开（公告）日：2011-09-08

  The present invention relates to polymers comprising one or more (repeating) unit(s) of the formula (I), and at least one (repeating) unit(s) which is selected from repeating units of the formula (II), (III) and (IV); and polymers of the formula III, or IV and their use as organic semiconductor in organic devices, especially in organic photovoltaics (solar cells) and photodiodes, or in a device containing a diode and/or an organic field effect transistor. The polymers according to the invention have excellent 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 organic field effect transistors, organic photovoltaics (solar cells) and photodiodes. A-D  (I) B-D  (II) A-E  (III) B-E  (IV)
• Pyrrolopyrrole derivatives, their manufacture and use
  申请人：BASF SE

  公开号：US20130172575A1

  公开（公告）日：2013-07-04

  The present invention relates to compounds of the formula I wherein the substituents are as defined in claim 1, and their use as organic semiconductor in organic devices, like diodes, organic field effect transistors and/or a solar cells. The compounds of the formula I have excellent solubility in organic solvents. High efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when said compounds are used in semiconductor devices or organic photovoltaic (PV) devices (solar cells).