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Updated: Jan 24, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Design and synthesis of a self-assembled photochemical dyad based on selective imidazole recognition
Dharam Paul1, Jennifer A Wytko, Matthieu Koepf
1Laboratoire d'Electrochimie, Université Louis Pasteur, UMR 7512 au CNRS, Institut Le Bel, 4 rue Blaise Pascal, 67070 Strasbourg, France.
Abstract:
The unique recognition properties of phenanthroline-strapped zinc porphyrin 1, which displays extremely high affinity for N-unsubstituted imidazoles, has been used as the driving force for the assembly of a photochemical dyad involving a zinc(II) porphyrin as energy donor and a free base porphyrin as energy acceptor. The synthesis of the imidazole-substituted porphyrin is described together with the assembly of the dyad. (1)H NMR titrations confirm the formation of a 1/1 complex between 1 and 6, as well as insertion of the imidazole of the acceptor within the phenanthroline strap of the donor. Preliminary fluorescence quenching measurements show that efficient energy transfer occurs between the self-assembled components.
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