Organic nanotubes and belt shaped molecules based on norbornadiene tethers

Abstract

We have employed density functional theory to study and characterize a new family of belt shaped molecules which use the norbornadiene tether and aromatic molecules as linkers. Our results indicated that the inclusion of the norbornadiene unit eliminates the strain commonly associated with the synthesis of belt-shaped molecules. Polymerization of the latter proved to be an effective method towards the bottom-up synthesis of organic nanotubes with uniform properties. The band gap of the infinite nanotubes proposed can be engineered by changing the molecule which links the norbornadiene tethers. In effect, the gap of the pyrene/norbornadiene and coronene/norbornadiene based nanotubes were 2.9 eV and 0.9 eV, respectively, as indicated by HSE calculations. Among the six belts assayed, two can be used to separate the magic fullerenes C₁₈₀ and C₂₄₀, given that large interaction energies were found upon complexation.