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

doi:10.1007/s11705-022-2216-5

Front. Chem. Sci. Eng.

2023, Vol. 17

Issue (3) : 307-313 https://doi.org/10.1007/s11705-022-2216-5

RESEARCH ARTICLE

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

Bing Lu(

), Zhecheng Zhang, Meiyu Qi, Yuehua Zhang, Hualing Yang, Jin Wang, Yue Ding, Yang Wang, Yong Yao(

)

College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, China

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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.

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

Corresponding Author(s): Bing Lu,Yong Yao

Online First Date: 12 December 2022 Issue Date: 17 March 2023

Cite this article:

Bing Lu,Zhecheng Zhang,Meiyu Qi, et al. All-in-one functional supramolecular nanoparticles based on pillar[5]arene for controlled generation, storage and release of singlet oxygen[J]. Front. Chem. Sci. Eng., 2023, 17(3): 307-313.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-022-2216-5
https://academic.hep.com.cn/fcse/EN/Y2023/V17/I3/307

Scheme1 Chemical structures of WP5, G and TPP, and graphical representation of the application of the novel nanoparticles.

Scheme2 Synthesis route for compound G.

Fig.1 The ¹H NMR (400 MHz, CD₃OD:D₂O = 1:4, 298 K) spectra for (a) G (3.6 mmol·L^?1), (b) the mixture of G and WP5 (G:WP5 = 1:2, 10.8 mmol·L^?1) and (c) WP5 (7.2 mmol·L^?1).

Fig.2 (a) SEM image and (b) DLS data of the formed nanoparticles.

Fig.3 (a) The absorption spectra of the mixture of TPP (25 μmol·L^?1) and G (100 μmol·L^?1) in DMF under a 660 nm laser irradiation for different time; (b) the absorption spectra of the irradiated mixture of TPP (25 μmol·L^?1) and G (100 μmol·L^?1) in DMF, heated at different temperatures for 8 h.

Fig.4 (a) The absorption spectra of the nanoparticles in H₂O after 660 nm laser irradiation for different times; (b) the absorption spectra of the nanoparticles in H₂O after laser irradiation (660 nm) and of the irradiated nanoparticles after heating at different temperatures for 1 h; (c) the fluorescence spectra of the nanoparticles in H₂O after the laser irradiation for 1 h and of the irradiated nanoparticles after heating at 110 °C for 4 h; (d) the fluorescence changes of the SOSG (10 μmol·L^?1) in the presence of the irradiated nanoparticles in H₂O after heating at 80 °C for different time.

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