Pictet–Spengler Synthesis of Quinoline-Fused Porphyrins and Phenanthroline-Fused Diporphyrins

Ke Gao; Norihito Fukui; Seok I. Jung; Hideki Yorimitsu; Dongho Kim; Atsuhiro Osuka

doi:10.1002/anie.201606293

Pictet–Spengler Synthesis of Quinoline-Fused Porphyrins and Phenanthroline-Fused Diporphyrins

Ke Gao, Norihito Fukui, Seok I. Jung, Hideki Yorimitsu, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

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 Ni^IIor Zn^IIcation. The resultant metal complexes displayed further red shifted absorption spectra and molecular twists to effect an almost perpendicular arrangement of the two porphyrins.

Original language	English
Pages (from-to)	13038-13042
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	42
DOIs	https://doi.org/10.1002/anie.201606293
Publication status	Published - 2016 Oct 10

Bibliographical note

Funding 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.

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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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.",

author = "Ke Gao and Norihito Fukui and Jung, {Seok I.} and Hideki Yorimitsu and Dongho Kim and Atsuhiro Osuka",

note = "Funding 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. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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Pictet–Spengler Synthesis of Quinoline-Fused Porphyrins and Phenanthroline-Fused Diporphyrins

Abstract

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