The diazo coupling reaction of a tetraaza[14]annulene nickel(II) complex (1 with a series of para-substituted phenyldiazonium tetrafluoroborates led to the corresponding 7,16-bis(azophenyl) products. The nickel(II) complexes formed are approximate square-planar coordinations and diamagnetic. The olefinic proton signals at the 7,16-positions of the nickel(II) complexes are destroyed by the diazo coupling reaction in the NMR spectra. The carbon signals at the 7,16-positions exhibit downfield shifts of about 30 ppm with the diazo coupling reaction.