A novel bifunctional dye composed of spirobenzopyran and a cinnamoyl moiety was prepared and its photochromic behavior under the illumination of monochromatic UV light was investigated. This colorless bifunctional dye exhibits typical photochromism in both the film and in solution, through the structural and geometrical transformation from spirobenzopyran to merocyanine accompanied by a photocrosslinking reaction between the cinnamoyl moieties. Two kinds of photochemical reaction were selectively achieved by irradiation with monochromatic UV light at wavelengths of 275 and 365 nm, respectively. The effect of the selective photochemical reaction on the photochromism of the dye and its decaying behavior was investigated.