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Updated: Apr 11, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Zwitterionic N2O2-Type Protonated Dipyrrin Bearing a Phosphate Anionic Moiety as a pH-Responsive Fluorescence
Masaki Yamamura1, Hiroyuki Takizawa1, Tatsuya Nabeshima1
1Graduate School of Pure and Applied Sciences and Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571 Japan.
Abstract:
Zwitterionic protonated-dipyrrin 1 bearing a phosphate unit was synthesized from the N2O2-type tetradentate dipyrrin ligand. Compound 1 is in equilibrium with the deprotonated form 1' with a pKa value of 5.8. Compound 1 exhibited a pH-responsive fluorescence under physiological conditions; the fluorescence intensity increased in aqueous media as the pH increased. In living cells, 1 also exhibited emission responsive to pH. Thus, 1 should be applicable as a pH probe for detecting tumor cells.
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