Publication Date:
2017-11-21
Description:
The flavonoid-based macroinitiator was received for the first time by the transesterification reaction of quercetin with 2-bromoisobutyryl bromide. In accordance with the “grafting from” strategy, a naturally-occurring star-like polymer with a polar 3,3',4',5,6-pentahydroxyflavone core and hydrophobic poly( tert -butyl acrylate) (P t BA) side arms was synthesized via a simplified electrochemically mediated ATRP ( se ATRP), utilizing only 78 ppm by weight (wt) of a catalytic Cu II complex. To demonstrate the possibility of temporal control, se ATRP was carried out utilizing a multiple-step potential electrolysis. The rate of the polymerizations was well-controlled by applying optimal potential values during preparative electrolysis to prevent the possibility of intermolecular coupling of the growing polymer arms. This appears to be the first report using on-demand se ATRP for the synthesis of QC-(P t BA-Br) 5 pseudo -star polymers. The naturally-derived macromolecules showed narrow MWDs ( Đ = 1.08–1.11). 1 H NMR spectral results confirm the formation of quercetin-based polymers. These new flavonoid-based polymer materials may find applications as antifouling coatings and drug delivery systems. Beilstein J. Org. Chem. 2017, 13, 2466–2472. doi:10.3762/bjoc.13.243
Keywords:
flavonoidson-demand seATRPquercetin-based macromolecules
Electronic ISSN:
1860-5397
Topics:
Chemistry and Pharmacology
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