Abstract Herein, we present three new tetradentate C^N*N^C luminophores and their platinum(II) complexes. We describe the influence of the degree of fluorination at the phenylpyridine luminophore on the photophysical properties of the monomeric species. A blue-shift can be observed with increasing number of fluorine atoms (0–6), which is related to a growing HOMO-LUMO gap that reaches a maximum for four halogen moieties. Increasing degree of fluorination enables intermolecular Pt–Pt interactions and promotes emission from ³MMLCT states in amorphous solids and matrices, with the drawback of lowered solubility. A clear trend towards layered packing patterns in crystals has been observed within the series. This knowledge is important for the design and realization of triplet emitters with aggregation-controlled luminescence towards potential applications in optoelectronic devices.