Three dinuclear isophthalato-bridged nickel(II) complexes formulated as [Ni( rac-L)]( μ-IPA)(ClO) ( 1), [Ni( RR-L)]( μ-IPA)(ClO) ( 2) and [Ni( SS-L)]( μ-IPA)(ClO) ( 3) (L = 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyc-lotetradecane, IPA = isophthalic acid) have been isolated and characterized. Single crystal X-ray diffraction analyses revealed that the Ni(II) atoms have six-coordinated distorted octahedral environments, and the isophthalato ligand bridges two Ni(II) centres in a bis bidentate fashion to form dimers in all three complexes. The monomers of {[Ni( SS-L)]( μ-IPA)} are connected through intermolecular hydrogen bonds to generate one-dimensional left-handed helical chains in complex 3. The homochiral natures of complexes 2and 3have been confirmed by CD spectroscopy. [Figure not available: see fulltext.]