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
(This article belongs to the Special Issue 25th Anniversary of Molecules—Recent Advances in Inorganic Chemistry)
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.
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Keywords:
iron oxide; superparamagnetism; Diels–Alder reactions; organophosphonates; fluorescent dye
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited
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 StyleHe, 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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