A diazirine's central carbon is sp²-hybridized, facilitating conjugation to dye molecules

Abstract

A fluorene-conjugated diazirine is described, for which two-photon activation is demonstrated for the first time.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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BibTeX RIS

BibTeX

@article{michelini2026diazirines,
  title = {{A diazirine's central carbon is sp²-hybridized, facilitating conjugation to dye molecules}},
  author = {Lorenzo Michelini and Tanya Slaney and Seerat Virk and Estefanía Rafic and L. Charlie Qie and Klara Corejova and Mathieu Lepage and Stefania Musolino and Allen Oliver and Roberto Etchenique and W. David Hong and Gino Dilabio and Jeremy Wulff},
  journal = {Chemical Science},
  year = {2026},
  month = nov,
  doi = {10.1039/d4sc06427e},
  url = {https://hal.science/hal-04939066v1},
  note = {CC BY 4.0},
}

RIS

TY  - JOUR
TI  - A diazirine's central carbon is sp²-hybridized, facilitating conjugation to dye molecules
AU  - Lorenzo Michelini
AU  - Tanya Slaney
AU  - Seerat Virk
AU  - Estefanía Rafic
AU  - L. Charlie Qie
AU  - Klara Corejova
AU  - Mathieu Lepage
AU  - Stefania Musolino
AU  - Allen Oliver
AU  - Roberto Etchenique
AU  - W. David Hong
AU  - Gino Dilabio
AU  - Jeremy Wulff
PY  - 2026
DA  - 2026/11/03
JO  - Chemical Science
DO  - 10.1039/d4sc06427e
UR  - https://hal.science/hal-04939066v1
AB  - A fluorene-conjugated diazirine is described, for which two-photon activation is demonstrated for the first time.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.
SN  - 2041-6520
SN  - 2041-6539
ER  -

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