The formation and characterization of K and Cs complexes originating from the cooperativity of three non-covalent interactions is explored. The tridimensional preorganization of the naphthothiophene platform displays a favorable well-defined bay region combining a π fragment and a carbonyl moiety flanking a central sulfur atom. A joint theoretical and experimental infrared multiple photon dissociation (IRMPD) study allowed deciphering the key contribution of the orthogonal phenyl fragment to the elaboration of alkali metal complexes. In combination with S and CO interactions, the π-cation interaction significantly enhances the binding energies of naphthothiophene derivatives.
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