Synthesis and photolytic properties of 1,5-di-N,N′-dialkylaminoanthraquinones containing acryloyl groups

Several I,5-di-N,N'-dialkyaminoanthraquinones containing acryloyl groups were synthesized and characterized by Fourier transform infrared (FTIR) and H-1 NMR spectroscopy. The photophysical and photoinduction properties of these anthraquinone derivatives were examined in solution, in combination with free radical producing agents such as hexa-aryl-bis-imidazoles (HABI). When UV-vis absorption and fluorescence spectroscopy were employed to investigate the photophysical process, results showed that the photobleaching rate of N-alkylaminoanthraquinones containing an acrylate group and HABI was much faster than the acrylate group-free N-alkylaminoanthraquinone/HABI combination. N-alkylaminoanthraquinone induced polymerization of 2-phenoxyethyl acrylate (POEA)/N-vinyl carbazole (NVC)/cellulose acetate butyrate (CAB) mixtures was studied using real-time infrared spectroscopy (RTIR). It was found that the rate of polymerization was faster if the acryloyl groups were connected to the N,N'-dialkylaminoanthraquinone structure and that 1,5-di-N,N'-dialkylaminoanthraquinone containing acryloyl groups was more sensitive to visible light system. (C) 2012 Elsevier B.V. All rights reserved.