Abstract Two new organic rigid-rod linker compounds, dimethyl 5-(1-anthracenylethynyl)isophthalate and dimethyl 5-(4-(1-anthracenynyl)phenylethynyl)-isophthalate, were used to couple anthracene to the surface of TiO 2 (anatase) and ZrO 2 nanoparticle thin films. These anthracene-rigid-rod molecules have high extinction coefficients and absorbance spectra that are red-shifted relative to 9-anthracenecarboxylic acid (9-AC). The rigid-rod linkers afford high surface coverages, ∼10 −8 mol/cm 2, on the nanostructured films in acetonitrile. Excimer-like emission on ZrO 2 nanoparticles suggests that the rigid-rods do not spatially isolate the anthracene chromophores effectively. On TiO 2 fluorescence was observed for both anthracene-rigid-rods while it was not detected for 9-AC consistent with quantitative electron injection into the semiconductor. Organoiodides and thallium cations (Tl +) were found to be heavy atom quenchers of the anthracene fluorescence in acetonitrile with a concentration dependence that followed the Stern–Volmer model. Fluorescence on ZrO 2 was quenched less efficiently by the organoiodides while Tl + cations exhibited enhanced quenching that followed the Stern–Volmer model at low Tl + concentrations and saturated at higher concentrations, behavior attributed to surface adsorption.