Synthesis and Characterization of Benzodioxinone Mono-telechelics and Their Use in Block Copolymerization

2021 Turkish journal of chemistry  
Poly(methyl methacrylate) (PMMA) and poly(ethylene glycol) methyl ether 10 (mPEG)-based monotelechelics were quantitatively prepared by copper (I)-catalyzed 11 azide/alkyne cycloaddition (CuAAC) click reactions using azido-terminated polymers 12 and alkyne functional benzodioxinones. The monotelechelic containing dimethyl 13 moities (2,2-dimethyl-5-(prop-2-yn-1-yloxy)-4H-benzo[d][1,3]dioxin-4-one) was heat-14 sensitive, whereas the monotelechelic containing diphenyl moieties (2,2-diphenyl-5-15
more » ... (2,2-diphenyl-5-15 (prop-2-yn-1-yloxy)-4H-benzo[d][1,3]dioxin-4-one) was UV light sensitive. Based on 16 the FT-IR, 1 H-NMR, and GPC investigations, the CuAAC click reactions enable the 17 quantitative syntheses of monotelechelics under mild conditions. Moreover, the 18 photosensitive mPEG-based monotelechelic was further utilized for the block 19 copolymer synthesis upon UV-light irradiation. The photoinduced acylation of mPEG 20 monotelechelic consist of (2,2-diphenyl-5-(prop-2-yn-1-yloxy)-4H-benzo[d][1,3]dioxin-21 4-one) in the presence hydroxy-terminated poly(epsilon caprolactone) enabled the 22 successful block copolymer formation. 23 2
doi:10.3906/kim-2104-22 fatcat:ldobhzpbpvel3bjpiijzjwczei