Facile access to pyridinium-based bent aromatic amphiphiles: nonionic surface modification of nanocarbons in water

Abstract
Efficient water-solubilization of nanocarbons is desirable for both their biological and material applications, but so far has mainly relied on covalent modifications or amphiphiles featuring ionic side-chains. Here, we report a facile 2–4-step synthesis of pyridinium-based, bent aromatic amphiphiles with modular nonionic side-chains (i.e., CH3 and CH2CH2(OCH2CH2)2–Y (Y = OCH3, OH, and imidazole)). The new amphiphiles quantitatively self-assemble into ≈2 nm-sized aromatic micelles in water independent of the side-chain. Importantly, efficient water-solubilization and nonionic surface modification of various nanocarbons (e.g., fullerene C60, carbon nanotubes, and graphene nanoplatelets) are achieved through noncovalent encircling with the bent amphiphiles. The resultant imidazole-modified nanocarbons display a pH-responsive surface charge, as evidenced by NMR and zeta-potential measurements. In addition, solubilization of a nitrogen-doped nanocarbon (i.e., graphitic carbon nitride) in the form of 10–30 nm-sized stacks is also demonstrated using the present amphiphiles.

Beilstein J. Org. Chem. 2024, 20, 32–40. doi:10.3762/bjoc.20.5

Source: Beilstein Journal of Organic Chemistry - January 8, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: aromatic micelle nanocarbon nonionic surface modification pyridinium water-solubilization Full Research Paper Source Type: research