Abstract
2-[10-Methyl-9-(N-butyl-N-p-toluenesulfonylcarbamoyl)-9,10-dihydro-9-acridinyloxy]ethyl methacrylate (AOEM) was synthesized as a monomer having a chemiluminescent moiety. Radical polymerization of AOEM using 2,2′-azobis(isobutyronitrile) at 50°C gave a homopolymer (Mn=2.88×104, Mw/Mn=2.23). Similarly, copolymers of AOEM with methyl methacrylate (MMA) were also obtained. The chemiluminescence spectrum of the homopolymer was consistent with that of AOEM or 10-methyl-9-(N-butyl-N-p-toluenesulfonylcarbamoyl)acridinium trifluoromethanesulfonate. One AOEM moiety of the polymer showed a light yield at 64% to 99% of the level of AOEM, and the total light yield was proportional to the release yield of 10-methyl-9-(N-butyl-N-p-toluenesulfonylcarbamoyl)acridinium salt from the polymer. Release of 10-methyl-9-(N-butyl-N-p-toluenesulfonylcarbamoyl)acridinium salts from both polymers and AOEM was observed under acidic conditions. Similar acidic release was also confirmed by measuring the time courses of light emission.
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Mitani, M., Koinuma, Y., Fugami, K. et al. Synthesis and Chemiluminescence of Polymers with a Releasable 10-Methyl-9-(N-butyl-N-p-toluenesulfonylcarbamoyl)acridinium Moiety. Polym J 28, 671–677 (1996). https://doi.org/10.1295/polymj.28.671
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DOI: https://doi.org/10.1295/polymj.28.671