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

Albert Marten Schulte, Lianne M Smid, Georgios Alachouzos*, Wiktor Szymanski*, Ben L Feringa*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

1 Citation (Scopus)
26 Downloads (Pure)

Abstract

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.

Original languageEnglish
Article numberD3CC05055F
Pages (from-to)578-581
Number of pages4
JournalChemical communications (Cambridge, England)
Volume60
Issue number5
Early online date14-Dec-2023
DOIs
Publication statusPublished - 16-Jan-2024

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