Cation delocalization and photo-isomerization enhance the uncaging quantum yield of a photocleavable protecting group

Photocleavable protecting groups (PPGs) enable the light-induced, spatiotemporal control over the release of a payload of interest. Two fundamental challenges in the design of new, effective PPGs are increasing the quantum yield (QY) of photolysis and red-shifting the absorption spectrum. Here we de...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-01, Vol.6 (5), p.578-581
Main Authors: Schulte, Albert Marten, Smid, Lianne M, Alachouzos, Georgios, Szymanski, Wiktor, Feringa, Ben L
Format: Article
Language:English
Subjects:
Absorption spectra
Chemistry
Isomerization
Parameter identification
Photolysis
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Summary:Photocleavable protecting groups (PPGs) enable the light-induced, spatiotemporal control over the release of a payload of interest. Two fundamental challenges in the design of new, effective PPGs are increasing the quantum yield (QY) of photolysis and red-shifting the absorption spectrum. Here we describe the combination of two photochemical strategies for PPG optimization in one molecule, resulting in significant improvements in both these crucial parameters. Furthermore, we for the first time identify the process of photo-isomerization to strongly influence the QY of photolysis of a PPG and identify the cis -isomer as the superior PPG. The combination of two photochemical strategies for PPG optimization in one molecule results in significant improvements in PPG photochemistry.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc05055f