A new chalcone derivative 3-(1-methyl-1H-pyrrol-2-yl)-1-naphthalen-2-yl propenone (MPNP) with electron donor-acceptor group has been synthesized and characterized by IR, (1)HNMR, (13)C NMR and X- ray crystallography. Electronic absorption and emission spectra of MPNP have been studied in solvents of different polarity. A remarkable red shift was observed in the emission spectrum of MPNP compared to the absorption spectrum upon increasing the solvent polarity, indicating a higher dipole moment in the excited state than in the ground state and the transition involved are π-π* with charge transfer character. Lippert-Mataga and Reichardts correlations were used to estimate the change in dipole moments (Δμ); suggest that the emissive state of MPNP is of strong ICT character. Fluorescence quantum yield (ϕf) of MPNP was correlated with empirical solvent polarity parameter ET(30), and it is observed that ϕf increases with increase in solvent polarity of polar aprotic solvents and decrease in alcoholic solvents. The interaction of MPNP with colloidal silver nanoparticles (AgNPs) was also studied in ethanol and ethylene glycol using steady state emission measurements. The fluorescence quenching data reveal that dynamic quenching and energy transfer play a major role in the fluorescence quenching of MPNP by Ag NPs.