copper 2,3,7,8,12,13,17,18-octakis[4-(trifluoromethyl)-phenyl]-5,10,15-triphenylcorrole | 1395342-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: copper 2,3,7,8,12,13,17,18-octakis[4-(trifluoromethyl)-phenyl]-5,10,15-triphenylcorrole
• 英文别名: copper β-octakis(p-trifluoromethylphenyl)-meso-triphenylcorrole
• CAS: 1395342-76-3
• 化学式: C₉₃H₄₇CuF₂₄N₄
• 分子量: 1739.93
• InChiKey: YZVIIUIENXWFFH-PWWSXFRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  copper 2,3,7,8,12,13,17,18-octakis[4-(trifluoromethyl)-phenyl]-5,10,15-triphenylcorrole 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以71.6%的产率得到
  参考文献：
  名称：

  Demetalation of copper undecaarylcorroles: Molecular structures of a free-base undecaarylisocorrole and a gold undecaarylcorrole

  摘要：

  Copper undecaarylcorroles were found to undergo acid-induced demetalation with unusual ease under both reductive and nonreductive conditions. The resulting free-base undecaarylcorroles were found to be rather reactive, readily photooxygenating to yield 5/10-hydroxyisocorroles and open-chain tetrapyrroles. The use of nonreductive conditions led to 50-75% yields of undecaarylisocorroles, a new class of sterically hindered ligands, of which one proved amenable to single-crystal X-ray structural analysis. In one case, interaction of an undecaarylisocorrole with gold(III) acetate resulted in aromatization of the macrocycle and a gold undecaarylcorrole. The Au complex exhibited Au-N distances of 1.941(3)-1.965(3) angstrom, and no significant non bonded interactions involving the gold. The significant solubility of this complex in organic solvents, compared with the relative insolubility of gold beta-octabromo-meso-triarylcorroles, appears to be related to the lack of aurophilic and metallophilic interactions. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2016.06.026
• 作为产物：
  描述：

  Cu[Br₈TPC] 、 4-三氟甲基苯硼酸 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 62.0h， 以82%的产率得到copper 2,3,7,8,12,13,17,18-octakis[4-(trifluoromethyl)-phenyl]-5,10,15-triphenylcorrole
  参考文献：
  名称：

  Undecaphenylcorroles

  摘要：

  A first major study of undecaphenylcorrole (UPC) derivatives is presented. Three different Cu-UPC derivatives with different para substituents X (X = CF3, H, CH3) on the beta-aryl groups were synthesized via Suzuki-Miyaura coupling of Cu[Br8TPC] and the appropriate arylboronic acid. A single-crystal X-ray structure of the X = CF3 complex revealed a distinctly saddled macrocycle conformation with adjacent pyrrole rings tilted by similar to 60-66 degrees relative to one another (within the dipyrromethane units), which is somewhat higher than that observed for beta-unsubstituted Cu-TPC derivatives but slightly lower than that observed for Cu[Br8TPC] (similar to 70 degrees) derivatives. Electrochemical and electronic absorption measurements afforded some of the first comparative insights into meso versus beta substituent effects on the copper corrole core. The Soret maxima of the Cu-UPC complexes (similar to 440-445 nm), however, are comparable to those of Cu[Br8TPC] derivatives and are considerably red-shifted relative to Cu-TPC derivatives. Para substituents on the beta-phenyl groups were found to tune the redox potentials of copper corroles more effectively than those on meso-phenyl substituents, a somewhat surprising observation given that neither the HOMO nor LUMO has significant amplitudes at the beta-pyrrolic positions.

  DOI：

  10.1021/ic301388e