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Updated: Jun 5, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
A diazirine's central carbon is sp2-hybridized, facilitating conjugation to dye molecules
Lorenzo Michelini1,2, Tanya Slaney1, Seerat Virk1
1Department of Chemistry, University of Victoria Victoria BC V8W 3V6 Canada wulff@uvic.ca.
Abstract:
Diazirines are versatile carbene precursors that are extensively used in biological target identification experiments. However, their photo-activation wavelength (ca. 365 nm) precludes their use in living organisms. Here we show that a reconceptualization of the diazirine hybridization state leads to conjugation of the diazirine motif to longer-wavelength chromophores. In a model diazirine-fluorene conjugate, we are able to achieve direct activation (and subsequent C-H insertion) with >450 nm light for the first time. Two-photon activation using near-IR light is also achieved, suggesting the possibility to prepare new diazirine probes for conducting target identification experiments in deep tissue.
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