Turning on the red phosphorescence of a [Ru(tpy)(bpy)(Cl)]Cl complex by amide substitution: self-aggregation, toxicity, and cellular localization of an emissive ruthenium-based amphiphileElectronic supplementary information (ESI) available: Experimental details, Graphical results, and videos. CCDC 1534260. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7cc02989f

Coupling the notoriously non-emissive complex [Ru(tpy)(bpy)Cl]Cl (tpy = 2,2′:6′,2′′-terpyridine, bpy = 2,2′-bipyridine) to a C 12 alkyl chain via an amide linker on the 4′ position of the terpyridine yielded a new amphiphilic ruthenium complex showing red emission and chloride-dependent aggregation properties. This emissive complex is highly cytotoxic in A549 non-small lung cancer cells where it can be followed by confocal microscopy. Uptake occurs within minutes, first by insertion into the cellular membrane, and then by migration to the peri-nuclear region. Dodecylamide functionalization of [Ru(tpy)(bpy)Cl]Cl led to an emissive, self-assembling, and cytotoxic complex targeting membranes.