Selective recognition of methyl viologen by an endo-functionalized naphthobox

Abstract

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 CH⋅⋅⋅N, CH⋅⋅⋅π, and π⋅⋅⋅π interactions with methyl viologen.