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Open AccessArticle

Reversible Diels–Alder Reactions with a Fluorescent Dye on the Surface of Magnetite Nanoparticles

Inorganic Solid-State Chemistry, Saarland University, Campus Building C4 1, 66123 Saarbrücken, Germany
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Academic Editors: Burgert Blom, Erika Ferrari, Vassilis Tangoulis, Cédric R. Mayer, Axel Klein and Constantinos C. Stoumpos
Molecules 2021, 26(4), 877; https://doi.org/10.3390/molecules26040877
Received: 31 December 2020 / Revised: 3 February 2021 / Accepted: 4 February 2021 / Published: 7 February 2021
Diels–Alder reactions on the surface of nanoparticles allow a thermoreversible functionalization of the nanosized building blocks. We report the synthesis of well-defined magnetite nanoparticles by thermal decomposition reaction and their functionalization with maleimide groups. Attachment of these dienophiles was realized by the synthesis of organophosphonate coupling agents and a partial ligand exchange of the original carboxylic acid groups. The functionalized iron oxide particles allow a covalent surface attachment of a furfuryl-functionalized rhodamine B dye by a Diels–Alder reaction at 60 °C. The resulting particles showed the typical fluorescence of rhodamine B. The dye can be cleaved off the particle surface by a retro-Diels–Alder reaction. The study showed that organic functions can be thermoreversibly attached onto inorganic nanoparticles. View Full-Text
Keywords: iron oxide; superparamagnetism; Diels–Alder reactions; organophosphonates; fluorescent dye iron oxide; superparamagnetism; Diels–Alder reactions; organophosphonates; fluorescent dye
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MDPI and ACS Style

He, S.; Kickelbick, G. Reversible Diels–Alder Reactions with a Fluorescent Dye on the Surface of Magnetite Nanoparticles. Molecules 2021, 26, 877. https://doi.org/10.3390/molecules26040877

AMA Style

He S, Kickelbick G. Reversible Diels–Alder Reactions with a Fluorescent Dye on the Surface of Magnetite Nanoparticles. Molecules. 2021; 26(4):877. https://doi.org/10.3390/molecules26040877

Chicago/Turabian Style

He, Siyang; Kickelbick, Guido. 2021. "Reversible Diels–Alder Reactions with a Fluorescent Dye on the Surface of Magnetite Nanoparticles" Molecules 26, no. 4: 877. https://doi.org/10.3390/molecules26040877

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