Copolyacrylates with phenylalanine and anthracene entities prepared by ATRP and microwave irradiation

In this study, two amino acid copolymers containing anthracene incorporated either on the one end, poly(N-acryloyl-L-phenylalanine-co-methyl methacrylate)-1 or as pendant groups, poly-(N-acryloyl-L-phenylalanine-co-methyl methacrylate)-2 were prepared directly from N-acryloyl-L-phenylalanine (APhe) and methyl methacrylate (MMA) through atom transfer radical polymerization (ATRP) and microwave-assisted synthesis. In the first case, 9-(chloromethyl)anthracene was used as an ATRP-initiator to obtain a copolymer that contains amino acid sequences and anthracene end-capped units (0.03 molar fraction). Rapid synthesis of copolymer under microwave irradiation (250 W) in the presence of 1,1'-azobis(cyclohexanecarbonitrile) used as an initiator was followed of a functionalization of the formed copolymer with an anthracene derivative yielding copolyacrylate with pendant anthracene (0.02 molar fraction). The structure of the copolymers was verified by H-1 NMR, UV-Vis and FTIR spectroscopy, gel permeation chromatography (GPC), and fluorescence spectroscopy. The fluorescence quenching process of anthracene which exists in copolymers by FeCl3, cobalt acetate, nitrobenzene, maleic anhydride, diethylaniline and nitromethane in DMF solutions shows that this involves an electron transfer between the excited state anthracene and the present transitional metal cations, more efficiently being FeCl3 for poly-(APhe-co-MMA)-1 and cobalt acetate for the latter copolymer. (C) 2010 Elsevier B.V. All rights reserved.