Chirality Inversion on the Carbon Dot Surface via Covalent Surface Conjugation of Cyclic α-Amino Acid Capping Agents
Fatemeh Ostadhossein, Gururaja Vulugundam, Santosh K. Misra, Indrajit Srivastava, Dipanjan Pan
Manipulating the chiroptical at the nanoscale is of great importance in stereoselective reactions, enantioseparation, self assembly and biological phenoma. In recent years, carbon dots have garnered great attention due to their favorable properties such as tunable fluorescence, high biocompatibility, and facile, scalable synthetic procedures. Herein, we report for the first time the unusual behavior of cyclic amino acids on the surface of carbon dots prepared via microwave-based carbonization. Various amino acids were introduced on the surface of carbon dots via EDC: NHS conjugation at room temperature. Circular dichroism results revealed that although most of the surface conjugated amino acids can preserve their chirality on negatively charged, ‘bare’ carbon dots, the ‘handedness’ of cyclic α-amino acids can be flipped when covalently attached on carbon dots. Moreover, these chiroptical carbon dots were found to interact with the cellular membrane or its mimic in a highly selective manner due to their acquired asymmetric selectivity. Comprehensive inhibitor study was conducted to investigate the pathway of cellular trafficking of these carbon dots. Overall, it was concluded that chirality of amino acid on the surface of carbon dots could regulate many of the cellular processes.
Circular dichroism, Stereochemistry, Cotton effect, Nanostructures, Membrane interactions, Biochemistry, Materials