1,4-diketo-2,5-dihexylpyrrolo[3,4-c]pyrrole-3,6-diphenyl-4-pinacolato boron ester | 917099-82-2

• 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: 1,4-diketo-2,5-dihexylpyrrolo[3,4-c]pyrrole-3,6-diphenyl-4-pinacolato boron ester
• 英文别名: 2,5-Dihexyl-3,6-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione；2,5-dihexyl-1,4-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 917099-82-2
• 化学式: C₄₂H₅₈B₂N₂O₆
• 分子量: 708.554
• InChiKey: WRIFFUXGOYYCCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  52
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-diketo-2,5-dihexylpyrrolo[3,4-c]pyrrole-3,6-diphenyl-4-pinacolato boron ester 、 3-(5-溴-2-噻吩基)-2,5-双(2-乙基己基)-2,5-二氢-6-(2-噻吩基)吡咯并[3,4-C]吡咯-1,4-二酮 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 1-[4-[5-[2,5-Bis(2-ethylhexyl)-3,6-dioxo-1-thiophen-2-ylpyrrolo[3,4-c]pyrrol-4-yl]thiophen-2-yl]phenyl]-4-[4-[5-[2,5-bis(2-ethylhexyl)-3,6-dioxo-1-thiophen-2-ylpyrrolo[3,4-c]pyrrol-4-yl]thiophen-2-yl]phenyl]-2,5-dihexylpyrrolo[3,4-c]pyrrole-3,6-dione
  参考文献：
  名称：

  Tri-Diketopyrrolopyrrole Molecular Donor Materials for High-Performance Solution-Processed Bulk Heterojunction Solar Cells

  摘要：

  Two new high-performance DPP-containing donor molecules employing a molecular architecture with three DPP chromorphores (tri-DPP) in conjugated backbones are synthesized and characterized. The two tri-DPP molecules with only a structural difference on alkyl substitutions, when blended with PC71 BM, lead to power conversion efficiencies up to 4.8 and 5.5%, respectively.

  DOI：

  10.1002/adma.201302007
• 作为产物：
  描述：

  3,6-bis(4-bromophenyl)-2,5-dihydropyrrolo[3, 4-c]pyrrole-1,4-dione 在 palladium diacetate potassium tert-butylate 、 potassium acetate 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1,4-diketo-2,5-dihexylpyrrolo[3,4-c]pyrrole-3,6-diphenyl-4-pinacolato boron ester
  参考文献：
  名称：

  Red Emitting N-Functionalized Poly(1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole) (Poly-DPP):  A Deeply Colored Polymer with Unusually Large Stokes Shift

  摘要：

  New pi-conjugated polymers are described, which entirely consist of aryl-aryl-coupled 1,4-diketo-2,5-dialkyl-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) units. The alkyl groups are n-hexyl (4a) or 2-ethylhexyl (4b) groups. The polymers are synthesized using nickel-promoted and palladium-catalyzed one-pot coupling reactions starting from 1,4-diketo-2,5-dialkyl-3,6-di(4-bromophenyl)pyrrolo[3,4-c]pyrrole (dibromo-DPP) as monomer, or conventional palladium-catalyzed coupling of dibromo-DPP and the 3,6-bis(pinacolato)boronester derivative of DPP. Polymers exhibit molecular weights up to 33 000 and are excellently soluble in chloroform and toluene. Deep red solutions (lambda(max) of 4b: 525 nm) with intense red photoemission (lambda(max) of 4b: 632 nm) and unusually large Stokes shift up to 107 nm are obtained. Cyclic voltammetry indicates quasi-reversible oxidation and reduction behavior, the onset potentials of 4b are +1.03 and -0.74 V vs SCE, respectively. From these potentials, HOMO/LUMO levels of -5.47 and -3.70 eV, respectively, can be calculated. Good solubility and processability into thin films render the compounds suitable for electronic applications.

  DOI：

  10.1021/ma061024e

文献信息

• Diketopyrrolopyrrole based A2-D-A1-D-A2 type small molecules for organic solar cells: Effects of substitution of benzene with thiophene
  作者：Yuan Zhao、Xue Zhou、Kailong Wu、Huan Wang、Shiwei Qu、Feng He、Chuluo Yang

  DOI：10.1016/j.dyepig.2016.03.033

  日期：2016.7

  diketopyrrolopyrrole core as the central acceptor unit, two oligomeric benzene or thiophene as the donor, and two isoindigo or benzothienoisoindigo as the weaker acceptor, were synthesized. The influence of the number of thiophene on optical physical, crystallinity, charge carrier mobility, the morphologies of blend films, electrochemical and photovoltaic properties was investigated. The absorption of the

  基于受体-供体-受体-供体-受体分子骨架的一系列小分子，其中包含一个二酮吡咯并吡咯核作为中心受体单元，两个低聚苯或噻吩作为供体，两个异靛蓝或苯并噻吩并异靛蓝作为弱受体合成的。研究了噻吩数目对光学物理性能，结晶度，电荷载流子迁移率，共混薄膜的形貌，电化学和光电性能的影响。二酮基吡咯并吡咯基化合物的吸收显示出红移的总体趋势是噻吩数量增加。由于苯被噻吩取代为供体，材料的最高占据分子轨道能级增加。X射线衍射测量表明所有这些材料具有强的结晶性。通过原子力显微镜和载体迁移率对形态进行表征，结果表明噻吩单元的数量影响了共混膜的微观结构和有机太阳能电池的性能。
• Red Emitting N-Functionalized Poly(1,4-diketo-3,6-diphenylpyrrolo[3,4-<i>c</i>]pyrrole) (Poly-DPP):  A Deeply Colored Polymer with Unusually Large Stokes Shift
  作者：A. R. Rabindranath、Y. Zhu、I. Heim、B. Tieke

  DOI：10.1021/ma061024e

  日期：2006.11.1

  New pi-conjugated polymers are described, which entirely consist of aryl-aryl-coupled 1,4-diketo-2,5-dialkyl-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) units. The alkyl groups are n-hexyl (4a) or 2-ethylhexyl (4b) groups. The polymers are synthesized using nickel-promoted and palladium-catalyzed one-pot coupling reactions starting from 1,4-diketo-2,5-dialkyl-3,6-di(4-bromophenyl)pyrrolo[3,4-c]pyrrole (dibromo-DPP) as monomer, or conventional palladium-catalyzed coupling of dibromo-DPP and the 3,6-bis(pinacolato)boronester derivative of DPP. Polymers exhibit molecular weights up to 33 000 and are excellently soluble in chloroform and toluene. Deep red solutions (lambda(max) of 4b: 525 nm) with intense red photoemission (lambda(max) of 4b: 632 nm) and unusually large Stokes shift up to 107 nm are obtained. Cyclic voltammetry indicates quasi-reversible oxidation and reduction behavior, the onset potentials of 4b are +1.03 and -0.74 V vs SCE, respectively. From these potentials, HOMO/LUMO levels of -5.47 and -3.70 eV, respectively, can be calculated. Good solubility and processability into thin films render the compounds suitable for electronic applications.
• <i>Tri</i>-Diketopyrrolopyrrole Molecular Donor Materials for High-Performance Solution-Processed Bulk Heterojunction Solar Cells
  作者：Jianhua Liu、Yanming Sun、Preecha Moonsin、Martijn Kuik、Christopher M. Proctor、Jason Lin、Ben B. Hsu、Vinich Promarak、Alan J. Heeger、Thuc-Quyen Nguyen

  DOI：10.1002/adma.201302007

  日期：2013.11

  Two new high-performance DPP-containing donor molecules employing a molecular architecture with three DPP chromorphores (tri-DPP) in conjugated backbones are synthesized and characterized. The two tri-DPP molecules with only a structural difference on alkyl substitutions, when blended with PC71 BM, lead to power conversion efficiencies up to 4.8 and 5.5%, respectively.