A novel series of calix[4]arene derivatives were synthesized via a Pd-catalyzed Sonogashira coupling reaction from para-substituted iodobenzene and 25,27-dipropargyl-calix[4]arene.Fluorescence studies found that nitro-phenols clearly exhibited quenching effects on 2c.Moreover,we minimized the free energy of the complexes by theoretical calculations.As the result,the n-n stacking interactions take place between the 4-nitrophenol and calix[4Jarene,which may lead to the significant fluorescence quench. A novel series of calix [4] arene derivatives were synthesized via a Pd-catalyzed Sonogashira coupling reaction from para-substituted iodobenzene and 25,27-dipropargyl-calix [4] arene. Fluorescence studies studies that that nitro-phenols were exhibited significantly quenching effects on 2c. Moreover, we minimized the free energy of the complexes by theoretical calculations. As the result, the nn stacking interactions take place between the 4-nitrophenol and calix [4Jarene, which may lead to the significant fluorescence quench.