Dithienylnitrophenols were synthesized as precursors of π-electronic anions, which were stabilized by intramolecular chalcogen bonding, forming various ion pairs in combination with cations. The modes of solid-state charge-by-charge assemblies, along with solution-state stacking and photoinduced electron transfer behaviors, were modulated by the constituent ionic species.

A variety of naphthalenediolates were orthogonally introduced to the boron unit of dipyrrolyldiketone boron complexes, exhibiting electronic properties that depended on the substituting positions of the naphthyl moieties. Combining the anion complexes with countercations resulted in the formation of ion-pairing assemblies with supporting stacking interactions of the naphthyl units.

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