3-phenyl-6-(4-(piperidin-1-yl)phenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione | 128454-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-phenyl-6-(4-(piperidin-1-yl)phenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: 3-(Phenyl)-6-(4-piperidinophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
• CAS: 128454-79-5
• 化学式: C₂₃H₂₁N₃O₂
• 分子量: 371.439
• InChiKey: GMQYYRAFAOTRJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.44
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-6-(4-(piperidin-1-yl)phenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 、 2,4-二硝基氟苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 以69%的产率得到2,5-bis(2,4-dinitrophenyl)-3-phenyl-6-(4-(piperidin-1-yl)phenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  HOMO and LUMO energy levels of N,N′-dinitrophenyl-substituted polar diketopyrrolopyrroles (DPPs)

  摘要：

  A series of four [3,4-c]pyrrole-1,4-diones (diketopyrrolopyrroles, DPPs) with (substituted) phenyl rings in 3,6-positions was prepared by direct N,N'-arylation of corresponding diketopyrrolopyrrole pigments with 1-fluoro-2,4-dinitro-benzene. While the energies of the HOMO levels depend strongly on the nature of the p-substituehts on the 3,5-phenyl rings, the LUMO levels obtained by cyclic and rotating disc voltammetry were found to be almost independent of the substituent. The absorption spectra show either a hypsochromic or bathochromic shift with respect to parent pigments, depending on the electron-donating and -accepting character of the p-substituents. This behaviour was rationalized by density functional theory calculations, showing that highest occupied molecular orbital is delocalized over the whole 3,6-diphenyl-diketopyrrolopyrrole conjugated system as in the parent pigments, while low-lying LUMO is completely different from the precursors, as it is localized exclusively on the 2,4-dinitrophenyl substituents, i.e. its shape and energy are not affected by a substitution on the 3,6-phenyl rings. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.03.005

文献信息

• Absorption and fluorescence of soluble polar diketo-pyrrolo-pyrroles
  作者：Stanislav Luňák、Martin Vala、Jan Vyňuchal、Imad Ouzzane、Petra Horáková、Petra Možíšková、Zdeněk Eliáš、Martin Weiter

  DOI：10.1016/j.dyepig.2011.05.004

  日期：2011.12

  Six soluble derivatives of 3,6-diphenyl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione N-alkylated on pyrrolinone ring with polar substituents in para positions of pendant phenyl rings were synthesized: five of them are reported for the first time. Absorption and fluorescence spectra were studied in solvents of different polarity. The compounds show small solvatochromism of absorption and a moderate positive solvatochromism of fluorescence, especially when substituted by strong electron-donating piperidino substituent. A significant decrease of fluorescence quantum yields and its biexponential decay for dipolar derivatives in polar solvents was tentatively ascribed to the formation of twisted intramolecular charge transfer (TICT) excited state. All six compounds show fluorescence in polycrystalline solid-state with the maxima covering a range over 200 nm in visible and near infrared region. (C) 2011 Elsevier Ltd. All rights reserved.