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 NiIIor ZnIIcation. The resultant metal complexes displayed further red shifted absorption spectra and molecular twists to effect an almost perpendicular arrangement of the two porphyrins.
Bibliographical noteFunding Information:
This work was supported by Grants-in-Aid for Scientific Research from MEXT (Nos.: 25107002 (?Science of Atomic Layers?), 16H01019 (?Precisely Designed Catalysts with Customized Scaffolding?), 16H01149 (?Middle Molecular Strategy?)) and from JSPS (Nos.: 25220802 (Scientific Research (S)), 16H04109 (B), 24685007 (Young Scientists (A)) and 26620081 (Exploratory Research)). K.G. acknowledges a JSPS Postdoctoral Fellowship for Foreign Researchers. N.F. acknowledges a JSPS Fellowship for Young Scientists. H.Y. acknowledges Kansai Research Foundation for Technology Promotion and Asahi Glass Foundation for financial support. The work in Korea was supported by Global Research Laboratory 2013K1A1A2A02050183.
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