Inorganic Solid-State Chemistry, Saarland University, Campus Building C4 1, 66123 Saarbrücken, Germany.
Molecules. 2021 Feb 7;26(4):877. doi: 10.3390/molecules26040877.
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.
Diels-Alder 反应在纳米粒子表面允许纳米尺寸的构建块进行热可逆功能化。我们报告了通过热分解反应合成的磁性纳米粒子的合成及其与马来酰亚胺基团的功能化。这些双烯试剂的附着是通过合成有机膦酸酯偶联剂和对原始羧酸基团的部分配体交换来实现的。功能化的氧化铁颗粒允许通过在 60°C 下的 Diels-Alder 反应将呋喃基化罗丹明 B 染料共价连接到表面上。所得颗粒显示出罗丹明 B 的典型荧光。可以通过反 Diels-Alder 反应将染料从颗粒表面上裂解下来。该研究表明，可以将有机官能团热可逆地连接到无机纳米粒子上。
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