3,6-diphenyldihydropyrrolo[3,4-c]pyrrole-1,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3,6-diphenyldihydropyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: 1,4-Diphenyl-1,2,3a,4,5,6a-hexahydropyrrolo[3,4-c]pyrrole-3,6-dione
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: GETYYCAXUJXQQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-diphenyldihydropyrrolo[3,4-c]pyrrole-1,4-dione 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以24%的产率得到2,5-dibenzyl-3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  Impact of Systematic Structural Variation on the Energetics of π–π Stacking Interactions and Associated Computed Charge Transfer Integrals of Crystalline Diketopyrrolopyrroles

  摘要：

  Control over solid state structure is critical for effective performance in optoelectronic devices bearing if-conjugated charge mediating organic materials. A series of five structurally related N-benzyl-substituted diketopyrrolopyrroles (DPPs) differing solely in 2 out their 60 atoms were synthesized and crystal structures obtained. Systematic variation of the long axis aligned, pi-pi stacks has been identified within the single crystal structure series and intermolecular interaction energies and charge transfer integrals for the pi-pi stacks have been computed by means of density functional theory (M06-2X/6-311G(d)). The computed intermolecular interaction energies as well as charge transfer integrals were further investigated utilizing a series of systematically cropped dimer pairs, highlighting the crucial role of the benzyl/halo substitution on stabilization of these pi-pi dimers. Two of the DPPs, including a new polymorph of a previously reported structure exhibit twice the intermolecular interaction energy and comparable hole transfer integrals to Rubrene, one of the most efficient hole conducting materials known. The computed properties for all of the pi-pi dimer systems reported herein are consistent with trends predicted by a model system. As such these materials show great promise as charge mediators in organic electronic applications and may be exploited in systematic structure activity based investigations of charge transfer theory.

  DOI：

  10.1021/cg5010165
• 作为产物：
  描述：

  苯甲腈 、 丁二酸二甲酯 在 2-甲基-2-丁醇 、 potassium tert-butylate 作用下， 反应 2.0h， 以35%的产率得到3,6-diphenyldihydropyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  Impact of Systematic Structural Variation on the Energetics of π–π Stacking Interactions and Associated Computed Charge Transfer Integrals of Crystalline Diketopyrrolopyrroles

  摘要：

  Control over solid state structure is critical for effective performance in optoelectronic devices bearing if-conjugated charge mediating organic materials. A series of five structurally related N-benzyl-substituted diketopyrrolopyrroles (DPPs) differing solely in 2 out their 60 atoms were synthesized and crystal structures obtained. Systematic variation of the long axis aligned, pi-pi stacks has been identified within the single crystal structure series and intermolecular interaction energies and charge transfer integrals for the pi-pi stacks have been computed by means of density functional theory (M06-2X/6-311G(d)). The computed intermolecular interaction energies as well as charge transfer integrals were further investigated utilizing a series of systematically cropped dimer pairs, highlighting the crucial role of the benzyl/halo substitution on stabilization of these pi-pi dimers. Two of the DPPs, including a new polymorph of a previously reported structure exhibit twice the intermolecular interaction energy and comparable hole transfer integrals to Rubrene, one of the most efficient hole conducting materials known. The computed properties for all of the pi-pi dimer systems reported herein are consistent with trends predicted by a model system. As such these materials show great promise as charge mediators in organic electronic applications and may be exploited in systematic structure activity based investigations of charge transfer theory.

  DOI：

  10.1021/cg5010165

文献信息

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