A coumarin-terminated self-assembled monolayer on silver particles (C-SAM) from the reduction of silver ions in the presence of compound 3 was successfully prepared by utilizing phase transfer method, and analyzed by FTIR, SEM-EDS, UV-Visible and a particle sizer. The fluorescence behavior of coumarin termini was carried out in ethanol and chloroform with emission wavelength determined at 386 nm, suggesting an interaction between the carbonyl group and the solvent media. The dispersion was then investigated in acidic and basic conditions, showing a direct proportional correlation between the emission and the pH of the aqueous. These results were consistent for interpreting hydrogen bonds, particularly between the carbonyl group with either proton of the alcohol (C=O----H-O-R) or positive species in acidic conditions (C=O----H(+)). The interactions were possible only when the coumarin terminal rearranged in the monolayer and the carbonyl exerted towards the solvent media, while the rest of the molecules were separated from the solvents.