All-in-one functional supramolecular nanoparticles based on pillar[5]arene for controlled generation, storage and release of singlet oxygen

Abstract

The storage and controlled release of singlet oxygen (¹O₂) have attracted increasing attention due to the wide application and microsecond lifetime of ¹O₂ in water. Herein we provide an integrated nanoplatform consisting of a diphenylanthracene derivative, a water-soluble pillar[5]arene and a photosensitizer tetrakis(4-hydroxyphenyl)porphyrin (TPP), that may provide the controlled generation, storage and release of singlet oxygen. We design a new diphenylanthracene derivative with two trimethylammonium bromide groups on both ends that can be well recognized by the pillar[5]arene. The formed nanocarriers can be used to load TPP through their supramolecular self-assembly. The resulting nanoparticles show good water-solubility and uniform spherical morphology. After laser irradiation (660 nm), the nanoparticles exhibit excellent ability for the generation and storage of ¹O₂. When the irradiated nanoparticles are heated above 80 °C, ¹O₂ can be released from the system. Therefore, in this paper we pioneer the use of noncovalent interaction to integrate the diphenylanthracene derivatives and photosensitizers into one functional system, which provides a new strategy for the controlled generation, storage and release of singlet oxygen. We believe this groundbreaking strategy will have a great potential in providing necessary amounts of ¹O₂ for the photodynamic therapy of tumors in dark.

Graphical abstract

Keywords

storage and controlled release of singlet oxygen / supramolecular nanoparticles / noncovalent interactions / pillararenes / diphenylanthracene / photosensitizers

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (Grant Nos. 21801139, 21871227), the Innovation and Entrepreneurship Program of Jiangsu Province (Grant No. JSSCBS20211106) and the National Undergraduates Innovating Experimentation Project (Grant No. 202110304134H).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://dx.doi.org/10.1007/s11705-022-2216-5 and is accessible for authorized users.

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