5-[3,5-bis[2-[4-[1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboximido]phenyl]ethynyl]phenyl]dipyrromethane | 524960-84-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 5-[3,5-bis[2-[4-[1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboximido]phenyl]ethynyl]phenyl]dipyrromethane
• CAS: 524960-84-7
• 化学式: C₁₃₅H₁₁₂N₄O₁₀
• 分子量: 1950.4
• InChiKey: NWSSIEIBKRTEFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  34.56
• 重原子数：
  149.0
• 可旋转键数：
  17.0
• 环数：
  23.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  161.72
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (4-Ethynyl-phenyl)-{5-[{5-[hydroxy-(4-iodo-phenyl)-methyl]-1H-pyrrol-2-yl}-(2,4,6-trimethyl-phenyl)-methyl]-1H-pyrrol-2-yl}-methanol 、 5-[3,5-bis[2-[4-[1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboximido]phenyl]ethynyl]phenyl]dipyrromethane 在 ytterbium(III) triflate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc diacetate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 16.5h， 以10%的产率得到5-[3,5-bis[2-[4-[1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboximido]phenyl]ethynyl]phenyl]-10-(4-ethynylphenyl)-20-(4-iodophenyl)-15-mesitylporphinatozinc(II)
  参考文献：
  名称：

  Practical synthesis of perylene-monoimide building blocks that possess features appropriate for use in porphyrin-based light-harvesting arrays

  摘要：

  Perylene-monoimide dyes with solubilizing aryloxy substituents at the perylene perimeter and a synthetic handle on the N-aryl group are valuable building blocks for incorporation as accessory pigments in porphyrin-based light-harvesting arrays. A family of such dyes has been prepared by reaction of 1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboxylic anhydride with a set of 4-iodo/ethynyl anilines (with or without 2,6-diisopropyl substituents) in the presence of Zn(OAc)(2)(.)2H(2)O in imidazole/mesitylene at 130degreesC. The workup procedures throughout the synthesis have been streamlined for scale-up purposes, minimizing chromatography. Two bis(perylene)porphyrin building blocks were prepared in a rational manner and examined in Sonogashira and Glaser polymerizations. The two isopropyl groups on the N-aryl group and the three 4-tert-butylphenoxy groups at the perylene perimeter are essential for high solubility of the bis(perylene)porphyrins and corresponding oligomers in organic solvents. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00020-6
• 作为产物：
  描述：

  吡咯 、 3,5-bis[2-[4-[1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboximido]phenyl]ethynyl]benzaldehyde 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以96%的产率得到5-[3,5-bis[2-[4-[1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboximido]phenyl]ethynyl]phenyl]dipyrromethane
  参考文献：
  名称：

  Practical synthesis of perylene-monoimide building blocks that possess features appropriate for use in porphyrin-based light-harvesting arrays

  摘要：

  Perylene-monoimide dyes with solubilizing aryloxy substituents at the perylene perimeter and a synthetic handle on the N-aryl group are valuable building blocks for incorporation as accessory pigments in porphyrin-based light-harvesting arrays. A family of such dyes has been prepared by reaction of 1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboxylic anhydride with a set of 4-iodo/ethynyl anilines (with or without 2,6-diisopropyl substituents) in the presence of Zn(OAc)(2)(.)2H(2)O in imidazole/mesitylene at 130degreesC. The workup procedures throughout the synthesis have been streamlined for scale-up purposes, minimizing chromatography. Two bis(perylene)porphyrin building blocks were prepared in a rational manner and examined in Sonogashira and Glaser polymerizations. The two isopropyl groups on the N-aryl group and the three 4-tert-butylphenoxy groups at the perylene perimeter are essential for high solubility of the bis(perylene)porphyrins and corresponding oligomers in organic solvents. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00020-6