Fuchsonarenes are a recently reported class of macrocycles which have been utilised for their ability to act as multimodal molecular switches and as photosensitizers for singlet oxygen generations. They are an oxidised class of resorcinarenes, where the hybridization of the meso position via the oxidation of 3,5-di-tert-butyl-4-hydroxyphenol moieties has been altered. These applications of fuchsonarenes, which are unusual for their parent resorcinarenes, demonstrates the large effect variations in the meso carbon can have on the physical properties of these macrocycles. Their nanometric dimensions, rigid conformations and chemical stability make them interesting compounds for supramolecular chemistry. Additionally, the ability to synthesise different isomer forms (rctt and rccc), as well as, the possibility to further functionalise the resorcinol phenols makes them a versatile scaffold. Our studies to date demonstrate applications as molecular switches, photodynamic therapy agents and molecular rotors. This presentation will outline our current research towards the use of fuchsonarenes as photosensitizers for singlet oxygen production in an aqueous environment. We demonstrate the formation of stable water-soluble nanoparticles formed from fuchsonarene photosensitizers capable of generating singlet oxygen in vitro. These are synthesised using a precipitation method of a compact organic photosensitizer in the absence of surfactants or stabilizers. Due to the encryption of the chromophore within a compact and inflexible macrocyclic scaffold the photosensitizer is protected from the usual deactivation pathways caused by aggregation and conversely shows aggregation enhanced singlet oxygen generation properties due to the hindered environment within the nanoparticle.

Photosensitizer encryption in macrocycles with aggregation enhanced singlet oxygen production

ACS Spring 2022

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