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Two types of palladium(Ⅱ)-based metallacalixarenes [ML]2+and [ML2]2+have been synthesized through coordination-driven self-assembly from a series of flexible pyridine-bridged diimidazole ligands [2,6-bis ((1H-imidazol-1-yl)methyl) pyridine (L1), 2,6-bis((1H-benzo[d]imidazol-1-yl)methyl)pyridine (L2), 2,6-bis((1H-naphtho[2, 3-d]imidazol-1-yl)methyl)pyridine (L3)], with palladium(Ⅱ)-based building blocks [Pd(BF4)2(M1-BF4) and (tmeda)Pd(NO3)2 (M2-NO3) (tmeda = N,N,N ,N-tetramethyl-ethylenediamine)]. All complexes were characterized by NMR spectroscopy (1H NMR and 13C NMR), mass spectrometry (CSI-MS, ESI-HRMS) and elemental analysis. The single crystal X-ray diffraction analysis of [M1L22](NO3)2, [M1L32](NO3)2, [M1L32](PF6)2 and [M2L3](NO3)2 further confirmed the uniquely single bowl-shape and double bowl-shape structures. The anion binding properties within the metallacalixarenes as receptors were also investigated by NMR titration experiments in DMSO.