提高纳米金刚石羧酸含量的一般方法。
General Method to Increase Carboxylic Acid Content on Nanodiamonds.
机构信息
Laboratory of Single Molecule Biophysics, National Heart Lung and Blood Institute, National Institutes of Health, Building 50, Room 2134, Bethesda, MD 20892, USA.
Chemistry and Synthesis Center, National Heart Lung and Blood Institute, National Institutes of Health, Building B, Room 3040, 9800 Medical Center Drive, Rockville, MD 20850, USA.
出版信息
Molecules. 2022 Jan 23;27(3):736. doi: 10.3390/molecules27030736.
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 -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.
羧酸是一种常用的功能基团，用于碳纳米粒子的共价表面连接，通常通过酸氧化生成。然而，酸氧化会产生额外的含氧基团，包括环氧化物、酮、醛、内酯和醇。我们提出了一种方法，可以特异性地富集荧光纳米金刚石（FND）表面上的羧酸含量。氢化锂铝用于将含氧表面基团还原为醇。然后，通过铑（II）乙酸盐催化的卡宾插入反应与 -丁基重氮乙酸酯反应，将醇转化为羧酸，并通过三氟乙酸进行酯裂解。这种羧酸富集过程显著提高了纳米金刚石的均一性，并提高了 FND 表面功能化的效率。生物素功能化的荧光纳米金刚石被证明是稳定的单分子荧光和光学捕获探针。
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