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Studies Toward the Synthesis of Phenylacetylene Macrocycle Based Rotaxane Precursors as Building Blocks for Organic Nanotubes



Synthetic efforts toward the preparation of rotaxane precursors based on phenylacetylene macrocycles (PAM) are described. The aim of this study was to determine the optimal structural parameters to prepare high-molecular-weight rotaxane precursors through a strategy involving two Sonogashira couplings to attach bulky blockers on the PAM core. PAMs with different sizes and functions were prepared and coupled to different blockers to assess whether or not the resulting structure adopts a rotaxane-like conformation in which the rigid rod forms after the Sonogashira coupling threads through the PAM.

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