title: Pictet-Spengler Synthesis of Quinoline-Fused Porphyrins and Phenanthroline-Fused Diporphyrins.
abstract: 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.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.
authors.forename: Ke
authors.initials: K
authors.lastname: Gao
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.
authors.forename: Norihito
authors.initials: N
authors.lastname: Fukui
authors.affiliation: Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul, 120-749, Korea.
authors.forename: Seok Ii
authors.initials: SI
authors.lastname: Jung
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan. yori@kuchem.kyoto-u.ac.jp.
authors.forename: Hideki
authors.initials: H
authors.lastname: Yorimitsu
authors.affiliation: Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul, 120-749, Korea. dongho@yonsei.ac.kr.
authors.forename: Dongho
authors.initials: D
authors.lastname: Kim
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan. osuka@kuchem.kyoto-u.ac.jp.
authors.forename: Atsuhiro
authors.initials: A
authors.lastname: Osuka
keywords: heterocycles; nickel; porphyrinoids; supramolecular chemistry; zinc