Tuning Cycloparaphenylene Host Properties by Chemical Modification

[8]Cycloparaphenylene derivative 1 has been synthesized and its recognition abilities toward pyridinium guests have been investigated and compared with the [8]CPP macrocycle. The results showed a fine-tuning of the binding properties of [8]CPP 1 toward pyridinium cations due to the presence of the 1,4-DMB ring. DFT calculations indicate that the close steric fitting between the rigid cavity of 1 and the pyridinium guest is the crucial factor for the stabilization of their supramolecular complex through C–H···π and N + ···π 1,4DMB interactions.