Heterolysis vs Homolysis and <i>ortho</i> - <i>meta</i> -Effects in the Photohydrolysis of Biphenylamine Photocages
-O bond cleavage were analyzed. Mechanistic insights were obtained using computational studies, fluorescence spectroscopy, and laser flash photolysis. The reaction proceeds via a heterolytic cleavage in the excited state, followed by the formation of benzyl radicals (τ = 25-50 μs) upon relaxation to the ground state. These radicals either recombine to form oligomers or undergo further electron transfer in aqueous solution, producing carbocations and acetate. The synthetic applicability was demonstrated through benzoyl and palmitoyl esters, which underwent photochemical cleavage with yields exceeding 70%.
Authors
- Lidija Uzelac (ORCID: https://orcid.org/0000-0002-3076-7064)
- Marijeta Kralj (ORCID: https://orcid.org/0000-0002-7165-2722)
- Ivan Ljubić (ORCID: https://orcid.org/0000-0002-3395-7293)
- Igor Sviben
- Irena Škorić (ORCID: https://orcid.org/0000-0002-1563-7261)
- Vilma Lovrinčević
- Dragana Vuk (ORCID: https://orcid.org/0000-0002-1626-599X)
- Nikola Basarić (ORCID: https://orcid.org/0000-0001-9412-9734)
- Mélyne Baudin-Marie (ORCID: https://orcid.org/0009-0009-0202-3146)
Institutions
- University of Zagreb (HR)
- Ruđer Bošković Institute (HR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-04-17
- DOI
- https://doi.org/10.1021/acs.joc.6c00228
- Primary Topic
- Photochromic and Fluorescence Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Hrvatska Zaklada za Znanost