Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Tuning Cycloparaphenylene Host Properties by Chemical Modification

Tuning Cycloparaphenylene Host Properties by Chemical Modification
Placido Neri, Paolo Della Sala, Carmine Gaeta, Annunziata Soriente, Margherita De Rosa, Tonino Caruso, Carmen Talotta
[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+···π1,4DMB interactions.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01588

DOI: 10.1021/acs.joc.7b01588

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