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First Poly(2‐oxazoline)s with Pendant Amino Groups
Author(s) -
Cesana Sonia,
Auernheimer Jörg,
Jordan Rainer,
Kessler Horst,
Nuyken Oskar
Publication year - 2006
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200500495
Subject(s) - polymer chemistry , cationic polymerization , copolymer , monomer , chemistry , polymerization , oxazoline , ring opening polymerization , polymer , bifunctional , organic chemistry , catalysis
Summary: A new 2‐oxazoline monomer with a Boc protected amino function, 2‐[ N ‐Boc‐5‐aminopentyl]‐2‐oxazoline; ( Boc ‐ AmOx ), was synthesized from commercially available compounds. With an initiator salt system ( N ‐methyl‐2‐methyl‐2‐oxazolinium triflate; MeOxOTf ), the monomer could be converted via living cationic ring‐opening polymerization to well‐defined homopolymers with narrow molar mass distributions and targeted polymer chain length. After a quantitative deprotection, poly(2‐oxazoline)s with pendant amino functions were obtained. In order to vary the polymer functional group density and solubility of the polymer, copolymerization with different monomer ratios of Boc ‐ AmOx and 2‐ethyl‐2‐oxazoline ( EtOx ) was performed. Ex‐situ NMR spectroscopy studies verified the randomness of the cationic copolymerization. The accessibility of the pendant amino side functions was confirmed in polymer analog thiourea formation with different isothiocyanates, such as benzyl isothiocyanate ( BzNCS ), or a fluorescence dye, tetramethyl rhodamine isothiocyanate ( TRITC ). A cross‐linking reaction with a bifunctional isothiocyanate ( Ph(NCS) 2 ) resulted in poly(2‐oxazoline) hydrogels.