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Intrinsic green fluorescent cross-linked poly(ester amide)s by spontaneous zwitterionic copolymerization

Zia, A, Finnegan, JR, Morrow, JP, Yin, W, Jasieniak, JJ, Pentzer, E, Thickett, S ORCID: 0000-0002-8168-3856, Davis, TP and Kempe, K 2021 , 'Intrinsic green fluorescent cross-linked poly(ester amide)s by spontaneous zwitterionic copolymerization' , Biomacromolecules, vol. 22, no. 11 , pp. 4794-4804 , doi: 10.1021/acs.biomac.1c01087.

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Abstract

The spontaneous zwitterionic copolymerization (SZWIP) of 2-oxazolines and acrylic acid affords biocompatible but low molecular weight linear N-acylated poly(amino ester)s (NPAEs). Here, we present a facile one-step approach to prepare functional higher molar mass cross-linked NPAEs using 2,2′-bis(2-oxazoline)s (BOx). In the absence of solvent, insoluble free-standing gels were formed from BOx with different length n-alkyl bridging units, which when butylene-bridged BOx was used possessed an inherent green fluorescence, a behavior not previously observed for 2-oxazoline-based polymeric materials. We propose that this surprising polymerization-induced emission can be classified as nontraditional intrinsic luminescence. Solution phase and oil-in-oil emulsion approaches were investigated as means to prepare solution processable fluorescent NPAEs, with both resulting in water dispersible network polymers. The emulsion-derived system was investigated further, revealing pH-responsive intensity of emission and excellent photostability. Residual vinyl groups were shown to be available for modifications without affecting the intrinsic fluorescence. Finally, these systems were shown to be cytocompatible and to function as fluorescent bioimaging agents for in vitro imaging.

Item Type: Article
Authors/Creators:Zia, A and Finnegan, JR and Morrow, JP and Yin, W and Jasieniak, JJ and Pentzer, E and Thickett, S and Davis, TP and Kempe, K
Keywords: zwitterionic copolymerization, fluorescent nanoparticles, non-aqueous emulsions
Journal or Publication Title: Biomacromolecules
Publisher: Amer Chemical Soc
ISSN: 1525-7797
DOI / ID Number: 10.1021/acs.biomac.1c01087
Copyright Information:

© 2021 American Chemical Society

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