Nanoparticle Surface Functionalization-Aldehyde Modification (-CHO)

Aldehyde modification is an organic chemical reaction that involves the introduction of an aldehyde group (-CHO functional group) into a molecule, which is a functional group containing carbon, hydrogen and oxygen. Aldehyde modification reactions are usually achieved by oxidizing or reducing organic molecules. A common aldehyde reaction is the synthesis of aldehydes, in which an aldehyde group (-CHO) is introduced into the molecule. In addition, aldehyde groups can also be converted into other functional groups through redox reactions, such as carboxyl groups (-COOH) or alcohol groups (-OH).

Introduction to Nanoparticle Surface Aldehyde Modification

Surface aldehyde modification of nanoparticles is an important surface modification technique, which is achieved by introducing aldehyde (-CHO) molecules or groups on the surface of nanoparticles. This process is usually accomplished through chemical synthesis methods, involving different reaction pathways and conditions to control the density, distribution and properties of aldehyde groups.

Figure1. Schematic diagram of nanoparticle carriers with aldehyde groups modified on the surface.

Aldehyde modification can significantly change the surface properties and chemical activity of nanoparticles. First, it can provide reactive groups that can be used for further functionalization. This enables the nanoparticles to undergo specific chemical reactions with other molecules, ligands or multifunctional groups, thereby expanding their application areas. Aldehyde modification can also be used for the directional assembly of nanoparticles. For example, through reaction with amino compounds, stable connections of nanoparticles can be achieved to form more complex structures. In addition, side or terminal aldehyde can also regulate the surface charge distribution of nanoparticles, affecting their dispersion and interaction in solution. This is of great significance for the application of nanomaterials in fields such as catalysis, biomedicine, sensors, and materials science.

The specific features of nanoparticle surface aldehyde modification include:

Surface aldehyde modification of nanoparticles has some specific features and properties that can influence their performance in different applications. The following are the specific characteristics of surface aldehyde modification of nanoparticles:

• Chemical reactivity of aldehyde group: Aldehyde group (-CHO) is a highly reactive functional group that can react chemically with a variety of functional groups, such as hydroxyl, amine and thiol groups. This reactivity enables nanoparticle surface aldehydes to be used for further chemical modification and functionalization.
• Capable of coupling and cross-linking: Aldehyde groups can be used as coupling agents to connect nanoparticles to other molecules or materials, thereby achieving directional assembly and cross-linking of nanoparticles. This is useful for preparing complex multi-component structures and nanocomposites.
• Surface charge distribution control: The introduction of aldehyde groups can change the surface charge density and distribution of nanoparticles, thereby affecting their dispersion and interaction in solution. This has important implications for the application of nanoparticles in catalysis and colloidal fields.
• Biocompatibility: Surface modification of surface aldehydes of nanoparticles can improve their biocompatibility, making them more suitable for biomedical applications such as drug delivery and bioimaging.

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• Silane-Based Aldehyde Functionalization: This method involves the use of silane compounds, such as aminosilane or hydroxysilane, to introduce aldehyde groups into the side or end groups of nanoparticles. Silane compounds often contain aldehyde functional groups that can react chemically with hydrogen groups or other reactive functional groups on the surface of the nanoparticles.
• Grignard Reaction: Grignard reagents usually react with halogenated aldehydes or ketones to form aldehyde functional groups. This reaction can be used to introduce aldehyde groups on the nanoparticle surface, depending on the choice of Grignard reagent and the reaction conditions.
• Carbonylation: Carbonyl groups (aldehyde groups) can be introduced on the side or end groups of nanoparticles through reaction with carbon monoxide or related compounds. This method usually requires high pressure and high temperature conditions.
• Oxidation: Aldehyde groups can also be formed on the surface of nanoparticles through oxidation reactions. Common oxidizing agents include oxygen or hydrogen peroxide in acidic media.
• Boron Aldehyde Functionalization: This is a method of introducing boron aldehyde groups on the side or end groups of nanoparticles, usually modified by boronic acid or boronic acid ester compounds.
• Enzymatic Aldehyde Functionalization: In the surface modification of biological nanoparticles, enzymes can be used as catalysts for the introduction of aldehyde groups.

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References

1. Takechi-Haraya Y, et al.; Current Status and Challenges of Analytical Methods for Evaluation of Size and Surface Modification of Nanoparticle-Based Drug Formulations. AAPS PharmSciTech. 2022, 23(5):150.
2. Khan AU, et al.; Selected nanotechnologies and nanostructures for drug delivery, nanomedicine and cure. Bioprocess Biosyst Eng. 2020, 43(8):1339-1357.