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 red light is also achieved, suggesting the possibility to prepare new diazirine probes for conducting target identification experiments in deep tissue.
Supplementary materials
Title
Electronic Supplementary Information
Description
Supplemental tables and figures, materials and methods, synthetic protocols, spectral data for new compounds, UV/Vis and DSC data.
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