Manipulating dynamic covalent bonds through direct photoisomerization.

ABSTRACT: The wide availability, ease of manipulation, and access to spatiotemporal control make light an attractive stimulus for controlling dynamic covalent chemistries/networks. In this work, a series of photo-isomerizable benzalisoxazolone (BIOx) thia-Michael (tM) acceptors were developed that exhibit an increase in thiol-bonding during irradiation with visible light (455-470 nm). In situ photo-NMR experiments demonstrate significant increases in the overall system K _eq (extent of bonding) for a variety of electronically-substituted BIOx tM acceptors. A combination of experimental and computational studies show that steric interactions between the β-phenyl ring and substituent on the isoxazolone in the E-isomer serve as a driving force for the increased K <

SUBMITTER: Dolinski ND 

PROVIDER: S-EPMC12590959 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature