A series of 1-pyrenyl chalcones have been synthesized by Crossed-Aldol condensation of 1-acetylpyrene and substituted benzaldehydes. The purities of these chalcones have been checked by their physical constants, UV, IR, NMR and MASS spectral data. The spectral data of these chalcones have been correlated with Hammett sigma constants, F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis, the effect of substituents on the spectral group frequencies have been discussed. The anti-microbial activities of these chalcones have been evaluated using Bauer-Kirby method.