3,6-bis(thiazol-2-yl)-pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione | 1224573-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,6-bis(thiazol-2-yl)-pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione
• 英文别名: 3,6-bis-thiazol-2-yl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione；1,4-diketopyrrolo[3,4-c]pyrrole；1,4-bis(1,3-thiazol-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1224573-44-7
• 化学式: C₁₂H₆N₄O₂S₂
• 分子量: 302.337
• InChiKey: RVAWDAWGIPKKBD-UHFFFAOYSA-N

物化性质

• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.98
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,6-bis(thiazol-2-yl)-pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione 在 18-冠醚-6 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Diketopyrrolopyrrole based small molecular semiconductors containing thiazole units for solution-processed n-channel thin-film transistors

  摘要：

  In this work, three diketopyrrolopyrrole-based conjugated small molecular semiconductors characterized by the combination of a diketopyrrolopyrrole (DPP) central core, thiazole pi-conjugated moiety, and dicyanovinyl end group with different alkyl side chain substituents, 2TzDPPA1-2DCV, 2TzDPPA2-2DCV, and 2TzDPPA3-2DCV were synthesized. These small molecules have a similar narrow band gap of about 1.50 eV and deep LUMO energy level at -4.30 eV. Under ambient conditions, electron mobilities of 0.28 cm(2) V-1 s(-1), 0.13 cm(2) V-1 s(-1), 0.25 cm(2) V s(-1) for solution processed thin films of 2TzDPPA1-2DCV, 2TzDPPA2.2DCV, and 2TzDPPA3-2DCV were obtained, due to high crystallinity and well-organized molecular stacking. Compared with the other two materials, thin films of 2TzDPPA1-2DCV enable the best OFET performance with desirable I-on/I-off rates exceeding of 10(7), attribute to the coefficient of smoother film morphology and stronger crystallinity. These results reveal that introducing the thiazole unit into the DPP-based conjugated skeleton is conducive to enhance the crystallinity and tailor LUMO energy levels which ensure good performance and excellent stability of these molecules as active materials for n-channel electronic devices.

  DOI：

  10.1016/j.dyepig.2018.12.059
• 作为产物：
  描述：

  2-氰基噻唑 、 di-tert-amyl succinate 在 iron(III) chloride 、 sodium 、 溶剂黄146 作用下， 以 2-甲基-2-丁醇 、 甲醇 、 水 为溶剂， 生成 3,6-bis(thiazol-2-yl)-pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione
  参考文献：
  名称：

  [EN] PYRROLOPYRROLE DERIVATIVES, THEIR MANUFACTURE AND USE AS SEMICONDUCTORS
  [FR] DÉRIVÉS DE PYRROLOPYRROLE, PROCÉDÉ DE FABRICATION DE CEUX-CI ET LEUR UTILISATION COMME SEMI-CONDUCTEURS

  摘要：

  本发明涉及式（I）的化合物，其中取代基如权利要求1所定义，并且它们在有机器件中的用途，例如二极管、有机场效应晶体管和/或太阳能电池中的用途作为有机半导体。式I的化合物在有机溶剂中具有优异的溶解性。当这些化合物用于半导体器件或有机光伏（PV）器件（太阳能电池）时，可以观察到高能量转换效率、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：

  WO2010115767A1

文献信息

• 四氯代二噻吩乙烯、聚合物及合成方法和有机薄膜晶体管应用
  申请人：天津大学

  公开号：CN111518074A

  公开（公告）日：2020-08-11

  本发明提供了四氯代二噻吩乙烯、聚合物及合成方法和有机薄膜晶体管应用；四氯代二噻吩乙烯的合成步骤较少，成本较低，并且具有高直接芳基化反应活性，通过直接芳基化聚合制备共轭聚合物半导体材料。含四氯代二噻吩乙烯的共轭聚合物可用于制备有机薄膜晶体管器件，该聚合物有利于电荷的传输，从而获得可以满足工业应用要求的迁移率性能。有机薄膜晶体管器件均表现出双极传输或n型传输性能。双极传输性能有机薄膜晶体管器件的电子和空穴迁移率最高值超过1.7cm2/V·s和0.8cm2/V·s，n型传输性能的有机薄膜晶体管电子迁移率最高值超过1.2cm2/V·s。
• PYRROLOPYRROLE DERIVATIVES, THEIR MANUFACTURE AND USE AS SEMICONDUCTORS
  申请人：Hayoz Pascal

  公开号：US20120095236A1

  公开（公告）日：2012-04-19

  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 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).

  本发明涉及式(I)中所述取代基的化合物，其中所述取代基如权利要求1所定义，并且它们作为有机半导体在有机器件中的使用，例如二极管、有机场效应晶体管和/或太阳能电池。式I的化合物具有优异的有机溶剂溶解性。当所述化合物用于半导体器件或有机光伏（PV）器件（太阳能电池）时，可以观察到高效能转换率、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。
• 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。
• High Quantum Efficiencies in Polymer Solar Cells at Energy Losses below 0.6 eV
  作者：Weiwei Li、Koen H. Hendriks、Alice Furlan、Martijn M. Wienk、René A. J. Janssen

  DOI：10.1021/ja5131897

  日期：2015.2.18

  Diketopyrrolopyrrole-based conjugated polymers bridged with thiazole units and different donors have been designed for polymer solar cells. Quantum efficiencies above 50% have been achieved with energy loss between optical band gap and open-circuit voltage below 0.6 eV.