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The self-assembly of (TMEDA)Pd(NO3)2 or (TMEDA)Pt(NO3)2 (where TMEDA = N 1,N 1,N 2,N 2-tetramethylethane-1,2-diamine) and anthracene- or ferrocene-based diimidazole ligands (L1–3) in aqueous solution affords a series of positively charged [M2L2]4+ dimetallomacrocycles. Their structures were characterized by 1H NMR and electrospray ionization mass spectrometry and in the cases of {[(TMEDA)Pd]2L1 2}(NO3)4 (1), {[(TMEDA)Pd]2L1 2}(PF6)4 (1a), and {[(TMEDA)Pd]2L3 2}(NO3)4 (4) by single-crystal X-ray diffraction analysis. Interestingly, the NMR spectra of 1 and 1a revealed that the difference of their structures, as confirmed by X-ray diffraction analysis, was that a NO3 – of 1 was encapsulated inside the cavity of the basket-shaped metallomacrocycle by C–H···O hydrogen bonds, while PF6 – of 1a was bound outside by C–H···F hydrogen bonds. The fluorescence titration experiment exhibited the formation of 1:1 host–guest complexation for anthracene-based positively charged [M2L2]4+-type metallomacrocycles with NO3 –. The interactions between metallomacrocycles and various anions were investigated via fluorescence titration and cyclic voltammetry studies, respectively.