Synthesis and characterization of benzodioxinone mono-telechelics and their use in block copolymerization

Authors

CUMALİ ÇELİK

DOI

10.3906/kim-2104-22

Abstract

Poly(methyl methacrylate) (PMMA) and poly(ethylene glycol) methyl ether (mPEG)-based monotelechelics were quantitatively prepared by copper (I)-catalyzed azide/alkyne cycloaddition (CuAAC) click reactions using azido-terminated polymers and alkyne functional benzodioxinones. The monotelechelic containing dimethyl moities (2,2-dimethyl-5-(prop-2-yn-1-yloxy)-4H-benzo[d][1,3]dioxin-4-one) was heat-sensitive, whereas the monotelechelic containing diphenyl moieties (2,2-diphenyl-5-(prop-2-yn-1-yloxy)-4H-benzo[d][1,3]dioxin-4-one) was UV light sensitive. Based on the FT-IR, 1 H-NMR, and GPC investigations, the CuAAC click reactions enable the quantitative syntheses of monotelechelics under mild conditions. Moreover, the photosensitive mPEG-based monotelechelic was further utilized for the block copolymer synthesis upon UV-light irradiation. The photoinduced acylation of mPEG monotelechelic consist of (2,2-diphenyl-5-(prop-2-yn-1-yloxy)-4H-benzo[d][1,3]dioxin-4-one) in the presence of hydroxy-terminated poly(epsilon caprolactone) enabled the successful block copolymer formation.

Keywords

Benzodioxinones, block copolymer, click chemistry, ketene chemistry, photoacylation

First Page

1115

Last Page

1124

Recommended Citation

ÇELİK, CUMALİ (2021) "Synthesis and characterization of benzodioxinone mono-telechelics and their use in block copolymerization," Turkish Journal of Chemistry: Vol. 45: No. 4, Article 11. https://doi.org/10.3906/kim-2104-22
Available at: https://journals.tubitak.gov.tr/chem/vol45/iss4/11