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-

摘要

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.