Conjugated, covalently bound nanotubes have great potential to be employed as chemical and mechanical sensors, as components of miniature electronic devices, and as vessels for targeted drug delivery systems. In order to create new classes of functional nanotubes with pre-defined diameters, lengths and tunable properties, we are linking rigid macrocyles together in a face-to-face manner under dynamic covalent self-assembly conditions. To achieve this goal, we have computationally designed and synthesized several new classes of macrocycles of varying shapes, including the asararenes (see Figure) and naphtalenediimide (NDI)-based triangles. The asararenes are a family of highly symmetrical, large, aromatic macrocycles, which are prepared by reacting asarol methyl ether (1,2,4,5-tetramethoxybenzene) with paraformaldehyde in the presence of boron trifluoride etherate (see: Schneebeli, S. T. et al. Chem. Eur. J. 2013 , 19, 3860�3868, Front Cover Article). The more recently developed NDI-triangles, which can also be linked into covalently bound conducting nanotubes, have been found to form radical anions delocalized fully over three NDI-units upon reduction. The host-guest chemistry of these novel, redox active macrocycles with radical anionic cavities and their potential usage as catalysts will be discussed. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/239nm/uploads/13562_figure1.jpg' alt='' />

Assembly of rigid macrocycles into functional covalent nanotubes

246th National Meeting (2013)

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