Professor Jeremy Wulff

Abstract

Diazirines—strained three-membered rings containing two doubly-bound nitrogens—have been used for over 40 years for the identification of protein binding partners of bioactive small molecules. Starting in 2019, our group leveraged diazirines to create a new family of universal polymer crossslinkers: reagents that could upgrade the performance of virtually any aliphatic polymer material, and that could be used for the direct photopatterning of polyethylene-like materials for printed circuit boards in 5G and 6G devices, or of quantum dots for next-generation display technologies. Through rigorous structure–function studies, we improved the efficacy of these crosslinkers by over 10-fold, and also (rather accidentally) found that we could shift their activation wavelength from 365 nm into the edge of the visible spectrum. This observation in turn led to a reconsideration of the hybridization state of the diazirine’s central carbon atom. By thinking of this atom as sp²-hybridized rather than sp³-hybridized, we were able to create new diazirine–chromophore conjugates that could be activated using longer wavelengths of light, and—for the first time ever—be triggered through two-photon activation. While still at an early stage, these new findings suggest the ability to use diazirines for biological target identification inside of living organisms. 

Leading References:

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2. S. F. Musolino et al., Chemical Science, 2021, 12, 12138.
3. S. F. Musolino et al., Polymer Chemistry, 2022, 13, 3833.
4. Bi et al., Angewandte Chemie International Edition 2023, e202304708.
5. Kandanarachchi et al., Macromolecular Rapid Communications 2024, 2400200.
6. Michelini et al., ChemRxiv 2024, DOI: 10.26434/chemrxiv-2024-bqp13.