Ring Closure Reaction of 19-Substituted Bilinones to 5-Oxaporphyrin Metal Complexes Induced by Zn2+ and Cu2+ —Application to Turn-on Red Fluorogenic Probes for Zinc Ions

The reaction of 19-phenoxybilinones with Zn2+ caused ring-closure to afford the 5-oxaporphyrin zinc complex under ambient conditions. While bilinones are non-fluorescent, the 5-oxaporphyrin zinc complex fluoresced red light. 19-Phenoxybilinone can be employed as a fluorogenic zinc ion sensor. Among...

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Bibliographic Details
Published in:Chemistry letters Vol. 50; no. 5; pp. 908 - 911
Main Authors: Kakeya, Kazuhisa, Fukagawa, Hiroyuki, Teraoka, Akihiro, Mizutani, Tadashi
Format: Journal Article
Language:English
Published: Tokyo The Chemical Society of Japan 05-05-2021
Chemical Society of Japan
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Summary:The reaction of 19-phenoxybilinones with Zn2+ caused ring-closure to afford the 5-oxaporphyrin zinc complex under ambient conditions. While bilinones are non-fluorescent, the 5-oxaporphyrin zinc complex fluoresced red light. 19-Phenoxybilinone can be employed as a fluorogenic zinc ion sensor. Among various metal ions, only Zn2+, Cu2+ and Co2+ can induce the ring closure reaction to yield 5-oxaporphyrin metal complexes, and only the zinc complex was fluorescent. Submicromolar Zn2+ can be detected by 19-phenoxybilinone both in organic solvents and aqueous solvents.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.200921