Photochromic properties of [2.2]paracyclophane-bridged imidazole dimer with increased photosensitivity by introducing pyrenyl moiety.

The photochromic [2.2]paracyclophane-bridged imidazole dimers show instantaneous coloration upon exposure to UV light and rapid fading in the dark. A new [2.2]paracyclophane-bridged imidazole dimer, pseudogem-PPI-DPI[2.2]PC, with high photosensitivity to UVA radiation was developed. To enhance the photosensitivity, we introduced pyrenyl moieties to the [2.2]paracyclophane-bridged imidazole dimer. The localized π-π* transition of pyrenyl moieties appears in the UVA radiation region by introducing a pyrenyl moietiy on the 4-position of the imidazole rings. The expansion of the π-electron system also affects the absorption spectrum of the colored species. The broad absorption band of the colored species covers the whole range of visible light region and its absorbance is approximately equal throughout the visible light region. Thus, pseudogem-PPI-DPI[2.2]PC shows the photochromic reaction coloring black upon light irradiation and successive fast thermal bleaching following the monoexponential kinetics with a time constant of 12 ms at room temperature.