Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.
Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul, 120-749, Korea.
Angew Chem Int Ed Engl. 2016 Oct 10;55(42):13038-13042. doi: 10.1002/anie.201606293.
Doubly and quadruply quinoline-fused porphyrins were effectively synthesized through a reaction sequence consisting of Suzuki-Miyaura coupling of β-borylated porphyrins with 2-iodoaniline and subsequent Pictet-Spengler cyclization. These quinoline-fused porphyrins display red-shifted absorption bands and higher electron-accepting abilities. This synthetic protocol also allowed the synthesis of phenanthroline-fused porphyrin dimers, which bound either a Ni or Zn cation. The resultant metal complexes displayed further red shifted absorption spectra and molecular twists to effect an almost perpendicular arrangement of the two porphyrins.
通过包含硼酸酯卟啉与 2-碘苯胺的 Suzuki-Miyaura 偶联以及随后的Pictet-Spengler 环化的反应序列，有效地合成了双和四喹啉并卟啉。这些喹啉并卟啉显示出红移的吸收带和更高的电子接受能力。该合成方案还允许合成菲咯啉并卟啉二聚体，其结合了 Ni 或 Zn 阳离子。所得的金属配合物显示出进一步的红移吸收光谱和分子扭曲，使两个卟啉几乎呈垂直排列。
