title: Comprehensive understanding of structure- photosensitivity relationships of photochromic [2.2]paracyclophane-bridged imidazole dimers.
abstract: The photochromic [2.2]paracyclophane-bridged imidazole dimers show instantaneous coloration upon exposure to UV light and rapid fading in the dark. Experimental details for the enhancement of the photosensitivity and the unique photoisomerization of newly designed [2.2]paracyclophane-bridged imidazole dimers are demonstrated. We explored the structure-property relationships and demonstrated an efficient strategy for designing high-performance fast-photochromic molecules with increased photosensitivity to solar UVA radiation. The [2.2]paracyclophane-bridged imidazole dimer consists of two types of imidazole rings, Im1 and Im2. Im1 is characterized by a 6π electron system with an electron-donating characteristic, whereas Im2 is distinguished by a 4π electron system with an electron-withdrawing characteristic. The introduction of electron-donating substituents into the phenyl rings attached to the electron-withdrawing Im2 was proved to enhance the photosensitivity with the aid of the intramolecular charge transfer transitions. The unique photoisomerization resulting from the changes in the bonding manner between two imidazole rings was also investigated in detail.
authors.affiliation: Department of Chemistry, School of Science and Engineering, Aoyama Gakuin University, Sagamihara, Kanagawa, Japan.
authors.forename: Katsuya
authors.initials: K
authors.lastname: Mutoh
authors.forename: Jiro
authors.initials: J
authors.lastname: Abe
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D019281:Dimerization; D007093:Imidazoles / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D017319:Photosensitizing Agents / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014466:Ultraviolet Rays
chemical_list: D001952:Bridged-Ring Compounds; D007093:Imidazoles; D017319:Photosensitizing Agents; D011083:Polycyclic Compounds; C515344:(2.2)paracyclophane; C029899:imidazole