2-butyl-3,6-bis(4-chlorochlorophenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione | 1213235-37-0

• 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-butyl-3,6-bis(4-chlorochlorophenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• 英文别名: 3,6-bis(4-chlorophenyl)-2-butyl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione；5-butyl-1,4-bis(4-chlorophenyl)-2H-pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1213235-37-0
• 化学式: C₂₂H₁₈Cl₂N₂O₂
• 分子量: 413.303
• InChiKey: DHTPCAAVERMUTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  正溴丁烷 、 颜料红254 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 2-butyl-3,6-bis(4-chlorochlorophenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 、 3,6-bis(4-chlorophenyl)-2,5-dibutyl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  Novel, soluble diphenyl-diketo-pyrrolopyrroles: Experimental and theoretical study

  摘要：

  Derivatives of diphenyl-diketo-pyrrolopyrrole, possessing electron-donating or withdrawing groups in the p-position of the phenyl, were synthesized and studied using optical characterization (absorption, fluorescence, time-resolved fluorescence) and quantum chemical calculation. An increase in absorption coefficient >= 10(5) dm(3) mol(-1) cm(-1) was observed using electron-donor groups; a bathochromic shift in both absorption and luminescence peaks was observed as a result of increased conjugation. Soluble derivatives were obtained by the introduction of alkyl groups (by N-alkylation) in the central pyrrolopyrrole unit. Calculated phenyl torsion angles using HF and B3LYP methods showed that the loss of molecule planarity reduced the extent of overlap between the pi-orbitals of the central pyrrolopyrrole unit and phenyls after N-alkylation. This treatment thus reduced both the bathochromic shift and increased absorption coefficient. The presence of the donor or acceptor groups in itself does not influence molecule planarity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2009.07.014

文献信息

• Novel, soluble diphenyl-diketo-pyrrolopyrroles: Experimental and theoretical study
  作者：M. Vala、J. Vyňuchal、P. Toman、M. Weiter、S. Luňák

  DOI：10.1016/j.dyepig.2009.07.014

  日期：2010.2

  Derivatives of diphenyl-diketo-pyrrolopyrrole, possessing electron-donating or withdrawing groups in the p-position of the phenyl, were synthesized and studied using optical characterization (absorption, fluorescence, time-resolved fluorescence) and quantum chemical calculation. An increase in absorption coefficient >= 10(5) dm(3) mol(-1) cm(-1) was observed using electron-donor groups; a bathochromic shift in both absorption and luminescence peaks was observed as a result of increased conjugation. Soluble derivatives were obtained by the introduction of alkyl groups (by N-alkylation) in the central pyrrolopyrrole unit. Calculated phenyl torsion angles using HF and B3LYP methods showed that the loss of molecule planarity reduced the extent of overlap between the pi-orbitals of the central pyrrolopyrrole unit and phenyls after N-alkylation. This treatment thus reduced both the bathochromic shift and increased absorption coefficient. The presence of the donor or acceptor groups in itself does not influence molecule planarity. (C) 2009 Elsevier Ltd. All rights reserved.
• US6790884B2
  申请人：——

  公开号：US6790884B2

  公开（公告）日：2004-09-14
• Preparation of Solvent Soluble Dyes Derived from Diketo-pyrrolo-pyrrole Pigment by Introducing an N-Alkyl group
  作者：Se-Hwa Choi、Oh-Tak Kwon、Na-Rim Kim、Chun Yoon、Jae-Pil Kim、Jae-Hong Choi

  DOI：10.5012/bkcs.2010.31.04.1073

  日期：2010.4.20