We present the synthesis and characterization of a series of neutral and cationic Nile Red cyclopalladated complexes, first examples of covalent coordination of Nile Red to a Pd(II) metal centre. The Pd(II) coordination sphere is completed by a series of ancillary substituted ligands (acetylacetonates or bipyridine derivatives) selected in order to tune the photophysical properties and/or to enhance the supramolecular order. Both neutral and cationic columnar rectangular metallomesogens have been obtained. Emission has been observed only for neutral complexes (both in solution and mesophase) but quenched in cationic complexes.