1,4-bis(5-piperidin-1-ylpyridin-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione | 1550168-25-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,4-bis(5-piperidin-1-ylpyridin-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1550168-25-6
• 化学式: C₂₆H₂₈N₆O₂
• 分子量: 456.547
• InChiKey: COSFNKKANLSMCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.46
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  三苯基硼烷 、 1,4-bis(5-piperidin-1-ylpyridin-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione 以 甲苯 为溶剂， 反应 24.0h， 以60%的产率得到
  参考文献：
  名称：

  Optical properties of highly planar diketopyrrolopyrrole derivatives fixed by coordinate bonds

  摘要：

  Diketopyrrolopyrrole (DPP) derivatives bearing 2-pyridyl groups were synthesized, which could serve as anionic N,N'-chelate ligands consisting of two nitrogen atoms of the lactam moieties and the pyridyl groups. Coordination of the DPP ligand to boron and platinum yielded the corresponding DPP complexes. Their crystal structures exhibited coplanar structures between the DPP core and the 2-pyridyl groups, which indicated extended pi-conjugation. The maximum absorption wavelength of the DPP complexes was longer than that of the corresponding DPP ligands. The choice of the introduced element affects the optical properties of the DPP complexes; the platinum complex has a longer absorption wavelength than the boron complex. The theoretical calculation revealed that these absorptions can be attributed to the pi-pi* transition. The introduction of the coordinating elements predominantly lowers the band gap. In addition, the substituent on the 2-pyridyl group can also modulate the energy levels. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.090
• 作为产物：
  描述：

  5-溴-2-氰基吡啶 在 iron(III) chloride 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2-甲基-2-丁醇 、 sodium 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 乙二醇二甲醚 、 2-甲基-2-丁醇 为溶剂， 反应 50.0h， 生成 1,4-bis(5-piperidin-1-ylpyridin-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione
  参考文献：
  名称：

  Optical properties of highly planar diketopyrrolopyrrole derivatives fixed by coordinate bonds

  摘要：

  Diketopyrrolopyrrole (DPP) derivatives bearing 2-pyridyl groups were synthesized, which could serve as anionic N,N'-chelate ligands consisting of two nitrogen atoms of the lactam moieties and the pyridyl groups. Coordination of the DPP ligand to boron and platinum yielded the corresponding DPP complexes. Their crystal structures exhibited coplanar structures between the DPP core and the 2-pyridyl groups, which indicated extended pi-conjugation. The maximum absorption wavelength of the DPP complexes was longer than that of the corresponding DPP ligands. The choice of the introduced element affects the optical properties of the DPP complexes; the platinum complex has a longer absorption wavelength than the boron complex. The theoretical calculation revealed that these absorptions can be attributed to the pi-pi* transition. The introduction of the coordinating elements predominantly lowers the band gap. In addition, the substituent on the 2-pyridyl group can also modulate the energy levels. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.090

文献信息

• Optical properties of highly planar diketopyrrolopyrrole derivatives fixed by coordinate bonds
  作者：Takuya Yamagata、Junpei Kuwabara、Takaki Kanbara

  DOI：10.1016/j.tet.2013.12.090

  日期：2014.2

  Diketopyrrolopyrrole (DPP) derivatives bearing 2-pyridyl groups were synthesized, which could serve as anionic N,N'-chelate ligands consisting of two nitrogen atoms of the lactam moieties and the pyridyl groups. Coordination of the DPP ligand to boron and platinum yielded the corresponding DPP complexes. Their crystal structures exhibited coplanar structures between the DPP core and the 2-pyridyl groups, which indicated extended pi-conjugation. The maximum absorption wavelength of the DPP complexes was longer than that of the corresponding DPP ligands. The choice of the introduced element affects the optical properties of the DPP complexes; the platinum complex has a longer absorption wavelength than the boron complex. The theoretical calculation revealed that these absorptions can be attributed to the pi-pi* transition. The introduction of the coordinating elements predominantly lowers the band gap. In addition, the substituent on the 2-pyridyl group can also modulate the energy levels. (C) 2014 Elsevier Ltd. All rights reserved.