Structure-function relationships in aryl diazirines reveal optimal design features to maximize C-H insertion.

ABSTRACT: Diazirine reagents allow for the ready generation of carbenes upon photochemical, thermal, or electrical stimulation. Because carbenes formed in this way can undergo rapid insertion into any nearby C-H, O-H or N-H bond, molecules that encode diazirine functions have emerged as privileged tools in applications ranging from biological target identification and proteomics through to polymer crosslinking and adhesion. Here we use a combination of experimental and computational methods to complete the first comprehensive survey of diazirine structure-function relationships, with a particular focus on thermal activation methods. We reveal a striking ability to vary the activation energy and activation temperature of aryl diazirines through the rational manipulation of electronic properties. Sign

SUBMITTER: Musolino SF 

PROVIDER: S-EPMC8457397 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature