Related Experiment Video
Updated: Nov 30, 2025

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties
Jiahui Ma1, Alexander Ripp1,2, Daniel Wassy1
1Institute of Organic Chemistry, University of Freiburg, Albertstr. 21, 79104 Freiburg, Germany.
Abstract:
Photocages have been successfully applied in cellular signaling studies for the controlled release of metabolites with high spatio-temporal resolution. Commonly, coumarin photocages are activated by UV light and the quantum yields of uncaging are relatively low, which can limit their applications in vivo. Here, syntheses, the determination of the photophysical properties, and quantum chemical calculations of 7-diethylamino-4-hydroxymethyl-thiocoumarin (thio-DEACM) and caged adenine nucleotides are reported and compared to the widely used 7-diethylamino-4-hydroxymethyl-coumarin (DEACM) caging group. In this comparison, thio-DEACM stands out as a phosphate cage with improved photophysical properties, such as red-shifted absorption and significantly faster photolysis kinetics.
More Related Videos
Related Concept Videos
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Thermal and Photochemical Electrocyclic Reactions: Overview
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...

