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Pictet–Spengler Synthesis of Quinoline‐Fused Porphyrins and Phenanthroline‐Fused Diporphyrins
Author(s) -
Gao Ke,
Fukui Norihito,
Jung Seok II,
Yorimitsu Hideki,
Kim Dongho,
Osuka Atsuhiro
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606293
Subject(s) - quinoline , porphyrin , phenanthroline , chemistry , photochemistry , absorption spectroscopy , absorption (acoustics) , metal , combinatorial chemistry , stereochemistry , crystallography , organic chemistry , materials science , physics , quantum mechanics , composite material
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 II or Zn II cation. The resultant metal complexes displayed further red shifted absorption spectra and molecular twists to effect an almost perpendicular arrangement of the two porphyrins.