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Acid–base controllable singlet oxygen generation in supramolecular porphyrin–gold nanoparticle composites tethered by rotaxane linkers

Shenzhen Key Laboratory of Polymer Science and Technology, College of Materials Science and Engineering, Shenzhen University, Xueyuan Boulevard 1066, Nanshan, Shenzhen 518055, China

Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College of Optoelectronic Engineering, Shenzhen University, Nanhai Boulevard 3688, Nanshan, Shenzhen 518060, China

Department of Biotechnology, Faculty of Life and Environmental Sciences, Graduate Faculty of Interdisciplinary Research, University of Yamanashi, 4-4-37 Takeda, Kofu 400-8510, Japan

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Chengjun Pan

Shenzhen Key Laboratory of Polymer Science and Technology, College of Materials Science and Engineering, Shenzhen University, Xueyuan Boulevard 1066, Nanshan, Shenzhen 518055, China

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Lei Wang

Shenzhen Key Laboratory of Polymer Science and Technology, College of Materials Science and Engineering, Shenzhen University, Xueyuan Boulevard 1066, Nanshan, Shenzhen 518055, China

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, and

Hideyuki Shinmori

Department of Biotechnology, Faculty of Life and Environmental Sciences, Graduate Faculty of Interdisciplinary Research, University of Yamanashi, 4-4-37 Takeda, Kofu 400-8510, Japan

E-mail Address: [email protected]

Corresponding author, tel: +81-55-220-8566.

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https://doi.org/10.1142/S108842461950086XCited by:5 (Source: Crossref)

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Abstract

Mechanically-interlocked photosensitizer–quencher systems based on free-base tetraphenylporphyrin (H₂TPP)–gold nanoparticle (AuNP) composites has been designed and synthesized by utilizing a rotaxane architecture comprised of secondary ammonium and crown ether subunit. The H₂TPP-substituted 24-crown-8 was able to shuttle along the alkanethiolate axle, triggered by deprotonation/protonation at the ammonium station, altering the H₂TPP–AuNP distance and the photoexcitation energy transfer efficiency. Upon switching, quantum yields for photosensitized singlet oxygen (¹O $_{2})$ generation and fluorescence after deprotonation were quenched by 46% and 42%, respectively. External environment-responsive ¹O₂ generation based on such a protonation/deprotonation-driven molecular switch is potentially advantageous for a variety of applications including photodynamic therapies.

Dedicated to Professor Atsuhiro Osuka in celebration of his 65th birthday.

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