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Substrate and product binding inside a stimuli-responsive coordination cage acting as a singlet oxygen photosensitizer

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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.

Graphical abstract: Substrate and product binding inside a stimuli-responsive coordination cage acting as a singlet oxygen photosensitizer

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Article information


Submitted
08 May 2020
Accepted
15 Jun 2020
First published
15 Jun 2020

This article is Open Access

Dalton Trans., 2020, Advance Article
Article type
Paper

Substrate and product binding inside a stimuli-responsive coordination cage acting as a singlet oxygen photosensitizer

S. Pullen, S. Löffler, A. Platzek, J. J. Holstein and G. H. Clever, Dalton Trans., 2020, Advance Article , DOI: 10.1039/D0DT01674H

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