2,5-dihexadecyl-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione | 1356822-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2,5-dihexadecyl-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• 英文别名: 2,5-Dihexadecyl-3,6-bis(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione；2,5-dihexadecyl-1,4-dithiophen-2-ylpyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1356822-73-5
• 化学式: C₄₆H₇₂N₂O₂S₂
• 分子量: 749.222
• InChiKey: BJVMPLWSEOIUKV-UHFFFAOYSA-N

物化性质

• 沸点：
  826.5±65.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  52
• 可旋转键数：
  32
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2,5-dihexadecyl-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 生成 3,6-bis(5-bromothiophen-2-yl)-2,5-dihexadecylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  Synthesis and structural analysis of dimethylaminophenyl-end-capped diketopyrrolopyrrole for highly stable electronic devices with polymeric gate dielectric

  摘要：

  报道了DPP(PhNMe₂)₂的合成和结构分析，它是一种稳定的二酮吡咯吡咯衍生物，末端带有强电子给体二甲胺基苯基团，详细分析了其环境稳定性的起源。

  DOI：

  10.1039/c8nj00545a
• 作为产物：
  描述：

  2-氰基噻吩 在 2-甲基-2-丁醇 、 sodium 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 2,5-dihexadecyl-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  Side-Chain Tunability of Furan-Containing Low-Band-Gap Polymers Provides Control of Structural Order in Efficient Solar Cells

  摘要：

  The solution-processability of conjugated polymers in organic solvents has classically been achieved by modulating the size and branching of alkyl substituents appended to the backbone. However, these substituents impact structural order and charge transport properties in thin-film devices. As a result, a trade-off must be found between material solubility and insulating alkyl content. It was recently shown that the substitution of furan for thiophene in the backbone of the polymer PDPP2FT significantly improves polymer solubility, allowing for the use of shorter branched side chains while maintaining high device efficiency. In this report, we use PDPP2FT to demonstrate that linear alkyl side chains can be used to promote thin-film nanostructural order. In particular, linear side chains are shown to shorten pi-pi stacking distances between backbones and increase the correlation lengths of both pi-pi stacking and lamellar spacing, leading to a substantial increase in the efficiency of bulk heterojunction solar cells.

  DOI：

  10.1021/ja2089662

文献信息

• Facile synthesis of arylthiophenyl-functionalized diketopyrrolopyrrole derivatives via direct C–H arylation: characterization and utilization in organic electronic devices
  作者：Akshaya Kumar Palai、Amit Kumar、Kyoseung Sim、Jaehyuk Kwon、Tae Joo Shin、Soonmin Jang、Sungwoo Cho、Seung-Un Park、Seungmoon Pyo

  DOI：10.1039/c5nj02631h

  日期：——

  for organic electronic devices. The properties of DPPs could be tuned by simple variation of the end groups such as t-butylphenyl, cyanophenyl and methoxynaphthyl. The effect of the substituent on the optical, electrochemical, and thermal properties of DPPs was evaluated using UV-visible spectroscopy, cyclic voltammetry, and thermogravimetric analysis. The morphology and molecular packing of thin-films

  通过钯催化的直接CHH芳基化反应，合成了一系列对称的芳基硫代苯基官能化的二酮吡咯并吡咯（DPP）衍生物，以开发用于有机电子设备的活性材料。DPP的性质可以通过端基的简单变化来调节，例如t-丁基苯基，氰基苯基和甲氧基萘基。使用紫外可见光谱，循环伏安法和热重分析法评估了取代基对DPP的光学，电化学和热学性质的影响。通过原子力显微镜（AFM），密度泛函理论（DFT）计算和二维掠入射X射线衍射（2D-GIXD）实验分析了DPP薄膜的形态和分子堆积。证明了合成的DPP在有机场效应晶体管中作为沟道材料的应用。
• Furan Conjugated Polymers Useful for Photovoltaic Applications
  申请人：Beaujuge Pierre M.

  公开号：US20120085992A1

  公开（公告）日：2012-04-12

  The present invention provides for a polymer comprising a π-conjugated backbone comprising a furan. The polymer has a narrow or low band gap and/or is solution processable. In some embodiments, the polymer is PDPP2FT or PDPP3F. The present invention also provides for a device comprising the polymer, such as a light-emitting diode, thin-film transistor, chemical biosensor, non-emissive electrochromic, memory device, photovoltaic cells, or the like.

  本发明提供了一种聚合物，其包括一个π-共轭骨架，其中包括呋喃。该聚合物具有窄或低带隙和/或可溶解性。在某些实施例中，该聚合物是PDPP2FT或PDPP3F。本发明还提供了一种包括该聚合物的器件，例如发光二极管、薄膜晶体管、化学生物传感器、非发光电致变色、记忆器件、光伏电池等。
• FUSED THIOPHENES, METHODS OF MAKING FUSED THIOPHENES, AND USES THEREOF
  申请人：He Mingqian

  公开号：US20130085256A1

  公开（公告）日：2013-04-04

  Described herein are compositions including heterocyclic organic compounds based on fused thiophene compounds, polymers based on fused thiophene compounds, and methods for making the monomers and polymer along with uses in thin film-based and other devices.

  本文描述了基于融合噻吩化合物的杂环有机化合物组合物，基于融合噻吩化合物的聚合物，以及制备单体和聚合物的方法，以及在薄膜和其他设备中的用途。
• Scalable Synthesis of Fused Thiophene-Diketopyrrolopyrrole Semiconducting Polymers Processed from Nonchlorinated Solvents into High Performance Thin Film Transistors
  作者：James R. Matthews、Weijun Niu、Adama Tandia、Arthur L. Wallace、Jieyu Hu、Wen-Ya Lee、Gaurav Giri、Stefan C. B. Mannsfeld、Yingtao Xie、Shucheng Cai、Hon Hang Fong、Zhenan Bao、Mingqian He

  DOI：10.1021/cm303953e

  日期：2013.3.12

  The synthesis and characterization of a fused thiophene-diketopyrrolopyrrole based semiconducting polymer PTDPPTFT4 is presented. A number of synthetic challenges have been overcome in the development of a practical scalable synthesis. Characterization by Gel Permeation Chromatography (GPC) over a range of temperatures has revealed the tendency of this polymer to aggregate even at elevated temperatures and confirmed that the molecular weight values obtained are for nonaggregated material. This polymer meets a number of important requirements for potential industrial applications, such as scalable synthesis, solubility in industrially suitable solvents, and material stability and processability into stable high performance thin film transistor devices. Computational modeling has been used to help explain the structure property relationships contributing to the high performance. Grazing incidence X-ray of the thin films showed out of plane lamellar packing and in plane pi-pi stacking, both good indicators of a preferentially oriented thin film, desirable for high charge carrier mobility. Hole mobilities in excess of 2 cm(2)/V.s, on/off ratio of >10(6), and threshold voltage <2 V have been achieved.
• [EN] FUSED THIOPHENES, METHODS OF MAKING FUSED THIOPHENES, AND USES THEREOF<br/>[FR] THIOPHÈNES FUSIONNÉS, PROCÉDÉS DE FABRICATION DE THIOPHÈNES FUSIONNÉS ET LEURS UTILISATIONS
  申请人：CORNING INC

  公开号：WO2013066973A1

  公开（公告）日：2013-05-10

  Described herein are compositions including heterocyclic organic compounds based on fused thiophene compounds, polymers based on fused thiophene compounds, and methods for making the monomers and polymer along with uses in thin film-based and other devices.