Aromatic aldehyde functionalized polycaprolactone and polystyrene macromonomers: synthesis, characterization and aldehyde-aminooxy click reaction

TitleAromatic aldehyde functionalized polycaprolactone and polystyrene macromonomers: synthesis, characterization and aldehyde-aminooxy click reaction
Publication TypeJournal Article
Year of Publication2012
AuthorsSane, PS, Tawade, BV, Palaskar, DV, Menon, SK, Wadgaonkar, PP
JournalReactive & Functional Polymers
Volume72
Pagination713-721
Date PublishedOCT
ISSN1381-5148
KeywordsAldehyde-terminated macromonomers, ATRP, Polycaprolactone, Polystyrene, ROP
Abstract

New bis-aldehyde functionalized initiators, viz, 4,4'-(4,4'-(5-hydroxypentane-2,2-diyl)bis(4,1-phenylene))bis(oxy)dibenza ldehyde (1) and 4,4'-bis(4-(4-(formylphenoxy) phenyl) pentyl 2-bromopropanoate (2) were synthesized starting from commercially available 4,4'-bis(4-hydroxyphenyl) pentanoic acid. These initiators were utilized, respectively, for ring opening polymerization of E-caprolactone and atom transfer radical polymerization of styrene. Well-defined polycaprolactone macromonomers (M-n(GPC): 2600-19400, PDI: 1.37-1.47) and polystyrene macromonomers (M-n(GPC): 2800-28200, PDI: 1.11-1.16) with bis-aldehyde functionality were synthesized. The kinetic study of styrene polymerization showed controlled polymerization behaviour. The presence of aldehyde functionality in macromonomers was confirmed by H-1 NMR spectroscopy. The reactivity of aldehyde functionality was demonstrated by carrying out aldehyde-aminooxy click reaction of polycaprolactone macromonomer with O-(2-azidoethyl) hydroxylamine which proceeded in a quantitative manner without backbone degradation. (C) 2012 Elsevier Ltd. All rights reserved.

DOI10.1016/j.reactfunctpolym.2012.06.020
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.505

Divison category: 
Polymer Science & Engineering