Non-covalent functionalization of multi-walled carbon nanotubes with organic aromatic compounds

Several aromatic compounds derived from benzene by its annelation (naphthalene, anthracene, phenanthrene, pyrene) and exocyclic substitution (e.g., nitrobenzene, dinitrobenzenes, trinitrobenzene, chlorobenzene, N,N-dimethylaniline, and others) and endocyclic substitution (pyridine, quinoline, isoquinoline) efficiently sorbed on multi-walled carbon nanotubes (MWCNTs). Equilibrium constants for the sorption process have been determined. Computations of the energy of formation were performed for surface complexes of those arenes on single-walled carbon nanotubes (SWCNTs). Formation energies of those complexes were correlated against the experimental equilibrium constants. The latter were also correlated against calculated LUMO energy of the arenes. Solely, limited tendencies to the linearity could be observed. The analysis of the results of the correlations indicated that the arenes acting as the charge acceptors formed stronger complexes than arenes with a high electron density in the molecular orbital, for instance, N, N-dimethylaniline. The area of the arene--SWCNT contact was very essential for the complexation. The proximity of the HOMO orbital of SWCNT and LUMO of the arene was another essential factor. Bulky substituents in the arene molecules obscured their efficient contact with SWCNT.