期刊
MOLECULES
卷 27, 期 3, 页码 -出版社
MDPI
DOI: 10.3390/molecules27030736
关键词
fluorescent nanodiamond; optical trapping; TIRF; rhodium catalysis; functionalization
资金
- Intramural Programs of the National Heart, Lung, and Blood Institute, and National Cancer Institute, National Institutes of Health [1ZIAHL006087-12]
- Intramural Program of the National Heart, Lung, and Blood Institute, National Institutes of Health
This article presents a method to enrich the carboxylic acid content on the surface of fluorescent nanodiamonds (FNDs). The method involves reducing oxygen-containing surface groups to alcohols and then converting them to carboxylic acids through a catalyzed reaction. This enrichment process improves the uniformity and functionalization efficiency of the nanodiamonds.
Carboxylic acid is a commonly utilized functional group for covalent surface conjugation of carbon nanoparticles that is typically generated by acid oxidation. However, acid oxidation generates additional oxygen containing groups, including epoxides, ketones, aldehydes, lactones, and alcohols. We present a method to specifically enrich the carboxylic acid content on fluorescent nanodiamond (FND) surfaces. Lithium aluminum hydride is used to reduce oxygen containing surface groups to alcohols. The alcohols are then converted to carboxylic acids through a rhodium (II) acetate catalyzed carbene insertion reaction with tert-butyl diazoacetate and subsequent ester cleavage with trifluoroacetic acid. This carboxylic acid enrichment process significantly enhanced nanodiamond homogeneity and improved the efficiency of functionalizing the FND surface. Biotin functionalized fluorescent nanodiamonds were demonstrated to be robust and stable single-molecule fluorescence and optical trapping probes.
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