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Frontiers of Chemical Science and Engineering >> 2023, Volume 17, Issue 3 doi: 10.1007/s11705-022-2216-5

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

Available online: 2022-12-12

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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.

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