The synthesis of discrete carbon nanotube segments of well-defined diameter, length and chiral vector remains a synthetic challenge, and the creation of such materials could provide starting materials for the synthesis of monodisperse samples of carbon nanotubes for a host of applications. We describe the synthetic strategy to use shape-persistent phenylene ethynylene macrocycles which can be 'folded' to create the nascent walls of the tube by making use of cycloadditions to the alkyne moieties of these macrocycles. Several macrocycles have been synthesized, which are potential precursors to armchair, zigzag and chiral nanotubes. Modeling of the cycloadditions reveals that the products should be accessible. Progress using Diels-Alder cycloadditions of the macrocyclic alkynes with cyclopentadienones as well as benzopyryliums formed by alkynylbenzaldehydes will be discussed.

Molecular origami: Folding phenylene ethynylene macrocycles into nanotube segments via cycloadditions

246th National Meeting (2013)

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