Selective recognition of methyl viologen by an endo-functionalized naphthobox

Highly selective binding of structurally similar substrates is common for biomolecular recognition, but is often challenging to realize in synthetic hosts. Herein, we report highly selective binding of methyl viologen over other analogues by an endo-functionalized naphthobox. X-ray single crystal structure and Density Functional Theory (DFT) calculations revealed that the endo-functionalized groups in the cavity of the naphthobox is important for the high binding selectivity through the formation of multiple C-H center dot center dot center dot N, C-H center dot center dot center dot pi, and pi center dot center dot center dot pi interactions with methyl viologen. (C) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.