2,5-dioctyl-3,6-bis(4-bromophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione | 889573-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2,5-dioctyl-3,6-bis(4-bromophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: 3,6-Bis(4-bromophenyl)-2,5-dioctyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione；1,4-bis(4-bromophenyl)-2,5-dioctylpyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 889573-58-4
• 化学式: C₃₄H₄₂Br₂N₂O₂
• 分子量: 670.528
• InChiKey: IRSVIOUBULQNOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  736.6±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-dioctyl-3,6-bis(4-bromophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione 、 9-蒽硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以58%的产率得到1,4-diketo-2,5-dioctyl-3,6-bis(9-anthrylphenyl)pyrrolo[3,4-c]-pyrrole
  参考文献：
  名称：

  9-基于蒽基的DPP基染料：芳基间距引起的差分光学性质

  摘要：

  尽管吡咯并[3,4- c ]吡咯-1,4（2 H，5 H）-二酮（DPP）广泛用作场效应晶体管和光伏有源层的构建基块，但对结构的关注却很少新型光学材料。在这项工作中，我们设计并合成了两种以苯和噻吩为间隔单元的可溶性9-蒽-封端的DPP衍生物，1,4-二酮-2,5-二辛基-3,6-双（9-蒽苯基）吡咯[ 3,4- c ]吡咯（ABDPP）和1,4-二酮-2,5-二辛基-3,6-双（9-蒽噻吩）吡咯[3,4- c]吡咯（ATDPP）。发现ABDPP和ATDPP在溶液中分别发出强荧光和弱荧光，但它们的结晶态均显示强荧光，这意味着尽管这两种染料均采用扭曲的共轭主链，但只有ATDPP表现出聚集增强发射（AEE）效应。 。有趣的是，研磨和压制只能将晶体ABDPP的荧光颜色从黄色变为红色，从而贡献了具有机械变色发光性的非AEE染料。差示扫描量热法和粉末X射线衍射分析证实，施加外部刺激后，结晶态和非晶态之间的相变是造成可逆颜色变化的原因。

  DOI：

  10.1039/c6tc02761j
• 作为产物：
  描述：

  4-溴苯腈 在 2-甲基-2-丁醇 、 18-冠醚-6 、 sodium tert-pentoxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2,5-dioctyl-3,6-bis(4-bromophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  Diketopyrrolopyrrole-Containing Polyfluorenes:  Facile Method To Tune Emission Color and Improve Electron Affinity

  摘要：

  A series of novel diketopyrrolopyrrole (DPP)-containing polyfluorenes, coded as PF-DPP01-50, were synthesized through palladium-catalyzed Suzuki polycondensation with different feed ratios between fluorene dibromide and DPP dibromide. Their chemical structures and compositions were verified by H-1 NMR and elemental analysis. DSC and TGA results show that they have good to excellent thermal stabilities. Absorption and photoluminescence (PL) properties of PF-DPP01-50, determined in both CHCl3 solutions and thin films, exhibit regular changes with increasing of DPP contents in copolymers, with absolute PL efficiencies being in the range 13.8-26.9%. Electroluminescence (EL) properties of all the copolymers were investigated with device configurations of ITO/PEDOT/copolymer/Ba/Al and ITO/PEDOT/copolymer/Al. A very low content of DPP units (1%) is needed to achieve full energy transfer from fluorene segments to DPP units; hence, exclusive emission of the latter occurs. EL colors of these copolymers vary from orange to red, corresponding to CIE coordinates from (0.52, 0.46) to (0.62, 0.37). The best performance was achieved by orange-emitting PF-DPP01 in device configuration of ITO/PEDOT/copolymer/Ba/Al, with maximum EQE of 0.45% and maximum brightness of 520 cd/m(2). Devices with configuration of ITO/PEDOT/copolymer/Al prove that DPP units can effectively improve the electron affinity of these copolymers. One of these devices (ITO/PEDOT/PF-DPP25/Al) can realize maximum EQE of 0.14% and maximum brightness of 127 cd/m(2). Therefore, color-tuning (red-shift) and improvement of electron affinity can be achieved at the same time through incorporation of DPP units.

  DOI：

  10.1021/ma0615349

文献信息

• Diphenylamine end-capped 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) derivatives with large two-photon absorption cross-sections and strong two-photon excitation red fluorescence
  作者：Er Qian Guo、Pei Hua Ren、Yan Li Zhang、Hai Chang Zhang、Wen Jun Yang

  DOI：10.1039/b911808j

  日期：——

  Novel donor–π-bridge–acceptor–π-bridge–donor (D–π–A–π–D)-type 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) derivatives with end-capping diphenylamine groups have been synthesized and shown to exhibit large two-photon absorption cross-sections over a wide range of wavelengths with strong two-photon excitation red fluorescence.

  新型供体-π桥-受体-π桥-供体（D-π-A-π-D）型 1,4-二酮-3,6-二苯基吡咯并[3,4-c]吡咯（DPP）衍生物已被合成，并显示其在宽波长范围内具有较大的双光子吸收截面，同时具有较强的双光子激发红色荧光。
• Conjugates of tetraphenylethene and diketopyrrolopyrrole: tuning the emission properties with phenyl bridges
  作者：Xiao Yuan Shen、Yi Jia Wang、Haoke Zhang、Anjun Qin、Jing Zhi Sun、Ben Zhong Tang

  DOI：10.1039/c4cc03024a

  日期：——

  Bridging DPP (ACQ-gen) and TPE (AIE-gen) with phenyls derived TPE–ph–DPP conjugates displaying enhanced and red-shifted emission in the solid state.

  用由苯基衍生的TPE-ph-DPP共轭物在固态下显示出增强和红移发射的方式，将DPP（ACQ-gen）和TPE（AIE-gen）桥接起来。
• Pd/C as a Clean and Effective Heterogeneous Catalyst for C–C Couplings toward Highly Pure Semiconducting Polymers
  作者：Shi-Yong Liu、Han-Ying Li、Min-Min Shi、Hao Jiang、Xiao-Lian Hu、Wang-Qiu Li、Lei Fu、Hong-Zheng Chen

  DOI：10.1021/ma3019238

  日期：2012.11.27

  Conjugated polymers are the primary blocks for organic electronics. Traditionally, Conjugated polymers synthesized via Suzuki, Heck, and Stille couplings are catalyzed by soluble homogeneous ligated palladiums, which suffer the contaminations of residual nano palladium and phosphine impurity resulting from side reaction of aryl-aryl exchange. To overcome these drawback's, a commercially available, clean, and ligand-free heterogeneous catalyst Pd/C for the C-C coupling polymerizations was developed in this work. The Pd/C catalyst showed increases in catalytic activity for Suzuki and Heck polymerizations, as compared with the classical homogeneous catalyst Pd(PPh3)(4). Furthermore, the Pd/C catalyst exhibited advantage of much less Pd residue in the resulting polymers, leading to better charge transport properties as demonstrated by field effect transistors.
• Synthesis and electroluminescence properties of fluorene-co-diketopyrrolopyrrole-co-phenothiazine polymers
  作者：Zhi Qiao、Junbiao Peng、Yi Jin、Qilin Liu、Jiena Weng、Zhicai He、Shaohu Han、Derong Cao

  DOI：10.1016/j.polymer.2009.12.044

  日期：2010.3

  A series of fluorene-co-diketopyrrolopyrrole(DPP)-co-phenothiazine polymers, named as Flu-DPP-Phen, were synthesized by a palladium-catalyzed Suzuki coupling reaction with different feed ratios among 9,9-dihexylfluorene-2,7-bis(trimethylene boronate), 2,5-dioctyl-3,6-bis(4-bromophenyl)pyrrolo[3,4c]pyrrole-1.4-dione, and 3.7-dibromo-10-octylphenothiazine. Their chemical structures and compositions were confirmed by H-1 NMR and elemental analysis. These terpolymers were found to be thermally stable and readily soluble in common organic solvents. Absorption and photoluminescence (PL) properties of Flu-DPP-Phen exhibit regular change with increasing of DPP contents in the terpolymers. Electroluminescence (EL) properties of all the terpolymers were characterized with the device configurations of ITO/PEDOT/terpolymer/Ba/Al and ITO/PEDOT/PVK/terpolymer/Ba/Al. Owing to exciton confinement on the narrow band gap DPP unit, the emission of fluorene segments is quenched completely with very low content of DPP (0.2 mol%). The EL spectra of all the terpolymers show exclusive long-wavelength emission originating from DPP units, which implied that the energy transfer in the terpolymer is very efficient. EL colors of the terpolymers vary from orange to red, the maximum emission is gradually red-shifted from 582 nm to 600 nm. The best EL performance was achieved by Flu-DPP-Phen(50:30:20) with maximum external quantum efficiency (EQE) of 0.25% and maximum brightness of 259 cd/m(2) in the device configuration of ITO/PEDOT/PVK/terpolymer/Ba/Al. The preliminary EL results proved that DPP units could effectively improve the electron affinity, and phenothiazine units could significantly enhance the hole injection ability, which resulted in the remarkable improvement of EQE. (C) 2010 Elsevier Ltd. All rights reserved.
• Diketopyrrolopyrrole-Containing Polyfluorenes:  Facile Method To Tune Emission Color and Improve Electron Affinity
  作者：Derong Cao、Qilin Liu、Wenjing Zeng、Shaohu Han、Junbiao Peng、Shouping Liu

  DOI：10.1021/ma0615349

  日期：2006.11.1

  A series of novel diketopyrrolopyrrole (DPP)-containing polyfluorenes, coded as PF-DPP01-50, were synthesized through palladium-catalyzed Suzuki polycondensation with different feed ratios between fluorene dibromide and DPP dibromide. Their chemical structures and compositions were verified by H-1 NMR and elemental analysis. DSC and TGA results show that they have good to excellent thermal stabilities. Absorption and photoluminescence (PL) properties of PF-DPP01-50, determined in both CHCl3 solutions and thin films, exhibit regular changes with increasing of DPP contents in copolymers, with absolute PL efficiencies being in the range 13.8-26.9%. Electroluminescence (EL) properties of all the copolymers were investigated with device configurations of ITO/PEDOT/copolymer/Ba/Al and ITO/PEDOT/copolymer/Al. A very low content of DPP units (1%) is needed to achieve full energy transfer from fluorene segments to DPP units; hence, exclusive emission of the latter occurs. EL colors of these copolymers vary from orange to red, corresponding to CIE coordinates from (0.52, 0.46) to (0.62, 0.37). The best performance was achieved by orange-emitting PF-DPP01 in device configuration of ITO/PEDOT/copolymer/Ba/Al, with maximum EQE of 0.45% and maximum brightness of 520 cd/m(2). Devices with configuration of ITO/PEDOT/copolymer/Al prove that DPP units can effectively improve the electron affinity of these copolymers. One of these devices (ITO/PEDOT/PF-DPP25/Al) can realize maximum EQE of 0.14% and maximum brightness of 127 cd/m(2). Therefore, color-tuning (red-shift) and improvement of electron affinity can be achieved at the same time through incorporation of DPP units.