Water-solubilization is the prerequisite to endow the pristinely hydrophobic fullerenes with biocompatibility and biofunctionality, which has been widely applied to derive fullerene-based nanomaterials for biomedical applications. Oxidation reactions using O2 and H2O2 are the most commonly used approaches to this end, through which fullerenols with different structural features can be obtained. Despite the progress in the syntheses and bioapplications of fullerenols, their formation mechanisms and structures at the atomic level, which substantialize their physical properties and biofunctions, have been little understood. Using density functional theory calculations, we comparatively study the mechanisms and product structures for the oxidations of C60, Gd@C60 and Gd@C82 using both O2 and H2O2 as oxidizing agents under both neutral and alkaline aqueous conditions. We predict the formation mechanisms and product structures corresponding to the different synthetic conditions. Briefly, the H2O2 oxidations of C60, Gd@C60 and Gd@C82 under neutral conditions do not occur readily at room temperature because of the high energy barriers, whereas the H2O2 oxidations can readily proceed under alkaline conditions. The oxygen-containing groups of the fullerenols obtained under these conditions include hydroxyl, carbonyl, hemiacetal and deprotonated vic-diol. In contrast, through O2 oxidation under alkaline conditions, the most probable oxygen-containing groups for C60 fullerenols are epoxide and deprotonated vic-diol, and those for Gd@C60 and Gd@C82 fullerenols are hydroxyls and carbonyls. The results explain a wide range of experimental findings reported before. More importantly, they provide atomistic-level insights into the formation mechanisms and structures for various fullerenols, which are of fundamental interest for understanding their biomedical applications in the future.
Related researches 71 articles
![<strong>Exploring the World of Fullerenols: A Deep Dive into Their Potential Medical Use</strong>](https://biofullerene.com/wp-content/uploads/2024/03/20-years-research-help-with-oncology-356x356.webp)
![Fullerenol has pronounced antiradical properties in the working concentration range](https://biofullerene.com/wp-content/uploads/2023/06/2021-se-rdm-molecules-all-312x356.png)
![The transcriptome profile of RPE cells by the fullerenol against hydrogen peroxide stress](https://biofullerene.com/wp-content/uploads/2022/12/antioxidant-vector-icon-radical-free-260nw-1596766771.jpg)
![Toxicity and Antioxidant Activity of Fullerenol C<sub>60,70</sub> with Low Number of Oxygen Substituents](https://biofullerene.com/wp-content/uploads/2022/12/antioxidant-vector-icon-radical-free-260nw-1596766771.jpg)
![Exploiting the physicochemical properties of dendritic polymers for environmental and biological applications](https://biofullerene.com/wp-content/uploads/2022/12/678-6786008_software-418x356.png)
![Impacts of fullerene derivatives on regulating the structure and assembly of collagen molecules](https://biofullerene.com/wp-content/uploads/2022/12/istockphoto-12085167-356x356.jpg)
![INHIBITORY POTENTIAL OF POLYHYDROXYLATED FULLERENES AGAINST PROTEIN TYROSINE PHOSPHATASE 1B](https://biofullerene.com/wp-content/uploads/2022/12/sol5379-356x356.jpg)
![The neuroprotective effect of fullerenols on a model of Parkinson’s disease in Drosophila melanogaster](https://biofullerene.com/wp-content/uploads/2022/12/PCORI-Story-Women-Pa-314x356.png)
![Effect of fullerenol nanoparticles on oxidative stress induced by paraquat in honey bees](https://biofullerene.com/wp-content/uploads/2022/12/1471354356_medonosny-1-500x293.jpg)
![Facile synthesis of highly water-soluble fullerenes more than half-covered by hydroxyl groups](https://biofullerene.com/wp-content/uploads/2022/12/360_F_308785794_MbgN-500x228.jpg)
![Interaction of fullerenol with lysozyme investigated by experimental and computational approaches](https://biofullerene.com/wp-content/uploads/2022/12/png-clipart-biomolec-500x284.png)
![Effects of hydroxyl group distribution on the reactivity, stability and optical properties of fullerenols](https://biofullerene.com/wp-content/uploads/2022/12/unnamed_1-500x349.jpg)
![Facile synthesis of isomerically pure fullerenols and formation of spherical aggregates from C60(OH)8](https://biofullerene.com/wp-content/uploads/2022/12/images.jpg)
![Influences of the size and hydroxyl number of fullerenes/fullerenols on their interactions with proteins](https://biofullerene.com/wp-content/uploads/2022/12/protein-3jpg57eb1785-356x356.jpg)
![The properties of small fullerenol cluster (C60(OH)24)7: computer simulation](https://biofullerene.com/wp-content/uploads/2022/12/unnamed-3-500x257.jpg)
![The structural studies of fullerenol C60(OH)24 and nitric oxide mixture in water solvent – MD simulation](https://biofullerene.com/wp-content/uploads/2022/12/n-a.jpg)
![Production of monoclonal antibodies against fullerene C60 and development of a fullerene enzyme immunoassay](https://biofullerene.com/wp-content/uploads/2022/12/hd-antibody-blue-485x356.png)
![Mechanism of taq DNA polymerase inhibition by fullerene derivatives: insight from computer simulations](https://biofullerene.com/wp-content/uploads/2022/12/1412-356x356.jpg)
![Polyhydroxylated C60 fullerene (fullerenol) attenuates neutrophilic lung inflammation in mice](https://biofullerene.com/wp-content/uploads/2022/12/11588808685cy47cvm6-412x356.png)
![Morphologically virus-like fullerenol nanoparticles act as the dual-functional nanoadjuvant for HIV-1 vaccine](https://biofullerene.com/wp-content/uploads/2022/12/hiv-356x356.png)
![Fullerenol C₆₀(OH)₃₆ could associate to band 3 protein of human erythrocyte membranes](https://biofullerene.com/wp-content/uploads/2022/12/1043132-356x356.png)
![Synthesis and Characterization of Hydroxyapatite/Fullerenol Nanocomposites](https://biofullerene.com/wp-content/uploads/2022/12/medicircle-nanomedic-500x281.jpg)
![Investigation of work of adhesion of biological cell (human hepatocellular carcinoma) by AFM nanoindentation](https://biofullerene.com/wp-content/uploads/2022/12/investigation-2-500x333.jpg)
![Self-assembling, reactivity and molecular dynamics of fullerenol nanoparticles](https://biofullerene.com/wp-content/uploads/2022/12/240fed07347d44de5685-356x356.png)
![Fullerenol C60(OH)24 increases ion permeability of lipid membranes in a pH-dependent manner](https://biofullerene.com/wp-content/uploads/2022/12/image3-358x356.png)
![Novel green PVA-fullerenol mixed matrix supported membranes for separating water-THF mixtures by pervaporation](https://biofullerene.com/wp-content/uploads/2022/12/istockphoto-12085167-356x356.jpg)
![Inhalable gadofullerenol/[70] fullerenol as high-efficiency ROS scavengers for pulmonary fibrosis therapy](https://biofullerene.com/wp-content/uploads/2022/12/istockphoto-12925559-440x356.jpg)
![Increasing the Resistance of Living Cells against Oxidative Stress by Nonnatural Surfactants as Membrane Guards](https://biofullerene.com/wp-content/uploads/2022/12/pngtree-an-icon-sign-356x356.jpg)
![Fullerenol C 60(OH) 36 protects human erythrocyte membrane against high-energy electrons](https://biofullerene.com/wp-content/uploads/2022/12/1-14308-500x281.jpg)
![Molecular Semiconductor Surfactants with Fullerenol Heads and Colored Tails for Carbon Dioxide Photoconversion](https://biofullerene.com/wp-content/uploads/2022/12/71092153-fe1fb500-21-500x343.png)
![Fullerenol Nanoparticles Eradicate Helicobacter pylori via pH-Responsive Peroxidase Activity](https://biofullerene.com/wp-content/uploads/2022/11/701f0ea8629699ea4b87-500x333.jpg)