The properties of single-wall carbon nanotubes (SWNTs) have become a prevalent topic of study in the scientific community in recent years. Covalent functionalization is used to tune their physical and electronic properties for applications in energy storage and optical devices, as well potentially separating metallic from semiconducting SWNTs. We investigated the 1,3-dipolar cycloaddition reactions of azomethine ylides with SWNTs using computational chemistry. Focal point analyses of the 1,3-dipolar cycloaddition reactions of the azomethine ylide with ethylene and benzene were compared with density functional theory (DFT) for use with larger systems [CCSD(T)/CBS vs. B3LYP-D/6-31G(d) and B97-D/TZV(2d,2p)]. These functionals were used as a benchmark for the same reaction with (6,6) SWNTs for two-layered ONIOM method geometries [B3LYP-D/6-31G(d) vs. B3LYP-D/6-31G(d)//B3LYP/6-31G(d):UFF and B97-D/TZV(2d,2p) vs. B97-D/TZV(2d,2p)// B97-D/TZV(2d,2p):UFF]. Future work will allow this method to be applied to larger systems, and adding substituents onto the ylide could alter the reactivity of the systems through stacking interactions.

??1,3-Dipolar cycloadditions of azomethine ylides: Prospects for covalent functionalization of carbon nanotubes????

245th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.