NDLI: Controlled folding of polystyrene single chains: design of asymmetric covalent bridges

Content Provider	Royal Society of Chemistry (RSC)
Author	Lutz, Jean-François Zamfir, Mirela Theato, Patrick
Copyright Year	2012
Abstract	α-Shaped polystyrene origamis with variable sizes and loop diameters were synthesized using a simple folding strategy. Linear polystyrene precursors containing precisely incorporated reactive functions (i.e. alkyne and activated ester moieties) were first synthesized by sequence-controlled copolymerization of styrene (donor comonomer) with functional N-substituted maleimides (acceptor comonomers). These copolymers were prepared by nitroxide mediated polymerization in the presence of a commercially available alkoxyamine (i.e. BlocBuilder® MA). Discrete amounts (i.e. one molar equivalent as compared to the alkoxyamine) of triisopropylsilyl-protected N-propargyl maleimide and pentafluorophenyl 4-maleimidobenzoate were added at precise moments during the polymerization of a large excess of styrene. Due to the kinetically favored cross-propagation of donor and acceptor comonomers, the N-substituted maleimides were incorporated in precise regions of the polystyrene chains. Linear precursors with variable chain-lengths and sequence distributions were synthesized and characterized using 1H NMR, size exclusion chromatography (SEC) and FT-IR spectroscopy. Afterwards the chains were folded in solution using a two-step strategy. The pentafluorophenyl activated ester moieties were first reacted with 11-azido-3,6,9-trioxaundecan-1-amine, thus leading to azide-functionalized polymers. Subsequently, intramolecular azide–alkyne Huisgen cycloadditions were performed in dilute DMF solutions in the presence of a copper-based catalyst. SEC, 1H NMR, and FT-IR measurements indicated the formation of folded polymer chains containing asymmetric covalent bridges.
Starting Page	1796
Ending Page	1802
Page Count	7
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	3
Issue Number	7
Journal	Polymer Chemistry
DOI	10.1039/c1py00514f
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Spectroscopy Nitroxide-mediated radical polymerization Maleimide Polymerization Polymer Fourier-transform infrared spectroscopy Rolf Huisgen Polystyrene SEC Ester Equivalent (chemistry) Comonomer Styrene Covalent bond Size-exclusion chromatography Nuclear magnetic resonance U.S. Securities and Exchange Commission Alkyne
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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