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Updated: Dec 17, 2025

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Substrate and product binding inside a stimuli-responsive coordination cage acting as a singlet oxygen
Sonja Pullen1, Susanne Löffler, André Platzek
1Faculty of Chemistry and Chemical Biology, TU Dortmund University, Otto-Hahn Str. 6, 44227 Dortmund, Germany. guido.clever@tu-dortmund.de.
Abstract:
An acridone-based, interpenetrated double cage [3BF4Pd4L8] acts as a photosensitizer for generating singlet oxygen which adds to 1,3-cyclohexadiene in a [2+4] hetero-Diels-Alder reaction to form 2,3-dioxabicyclo[2.2.2]oct-5-ene. Photocatalytic activity was exclusively observed for the assembled cage, whereas the free organic ligand L decomposes upon irradiation. While cage [3BF4Pd4L8] does not accept any organic guests, NMR, MS and single crystal X-ray results reveal that both substrate and product are readily encapsulated in the central pocket of its chloride-activated form [2Cl@Pd4L8]. The system combines multiple functions (photosensitization, allosteric activation and guest uptake) within a structurally complex, mechanically-bound self-assembly built up from a simple and readily accessible ligand.
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