diazirinecontaining

Diazirine-containing compounds are molecules that bear a diazirine functional group, a highly strained three-membered heterocycle with two adjacent nitrogen atoms. The diazirine moiety is valued for its light-activated reactivity, enabling covalent capture of nearby biomolecules or materials partners upon irradiation.

In the ground state, diazirines are relatively stable, but exposure to near-UV light cleaves the diazirine to expel nitrogen gas and generate a reactive carbene. This carbene can insert into nearby bonds such as C–H, N–H, or O–H, forming a covalent linkage between the diazirine-containing molecule and its surroundings. The resulting crosslinks enable capture of transient or weak interactions that are difficult to study by noncovalent methods.

Two common families of diazirine groups are alkyl diazirines and aryl diazirines, with trifluoromethyl diazirines being a widely used subclass. Aryl diazirines often generate carbenes with different lifetimes and wavelength requirements compared with alkyl variants, and trifluoromethyl diazirines can offer favorable photolysis efficiency and stability in many applications.

Applications of diazirine-containing tools span chemical biology and materials science. In biology, they are used as photoaffinity labels to map protein–ligand interactions, identify receptor partners, and profile proteomes. In materials science, diazirine crosslinkers enable solvent- or light-triggered bonding in polymers and hydrogels. Design choices—such as linker length, diazirine type, and placement—affect labeling radius, background reactivity, and overall efficiency.

Safety and handling considerations include the reactive carbene intermediates and potential UV exposure hazards. Work with diazirine-containing compounds should follow appropriate laboratory precautions and regulatory guidelines.