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Issue 18, 2014
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Amphiphilic block copolymers featuring a reversible hetero Diels-Alder linkage

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Abstract

The present article reports the preparation of a novel class of switchable amphiphilic diblock copolymers with a temperature switchable linkage. Reversible addition fragmentation chain transfer (RAFT) polymerization was used to synthesize the individual blocks: for the preparation of the non-polar block, i.e. poly(isoprene-co-styrene) (P(I-co-S)) (9200 g mol−1Mn ≤ 50 000 g mol−1, 1.22 ≤ Đ ≤ 1.36), a chain transfer agent (CTA, 3-((2-bromo-2-methylpropanoyl)oxy)propyl 2-(((dodecylthio)carbonothioyl)thio)-2-methylpropanoate) carrying a bromine group was employed, ready for subsequent cyclopentadienyl (Cp) transformation. For the preparation of the polar block, triethylene glycol methyl ether acrylate (TEGA) was polymerized (6600 g mol−1Mn ≤ 35 000 g mol−1, 1.12 ≤ Đ ≤ 1.30) using a RAFT agent carrying a phosphoryl Z-group, which is able to undergo hetero Diels-Alder (HDA) ligation with Cp moieties. Both building blocks were conjugated at ambient temperature in the presence of ZnCl2 as catalyst yielding the amphiphilic block copolymer P(I-co-S)-b-PTEGA (16 000 g mol−1Mn ≤ 68 000 g mol−1, 1.15 ≤ Đ ≤ 1.32). To investigate the bonding/debonding capability of the HDA linkage, high temperature nuclear magnetic resonance (HT-NMR) spectroscopy, high temperature dynamic light scattering (HT-DLS) and high temperature size exclusion chromatography (HT-SEC) were carried out, evidencing that efficiently switchable amphiphilic block copolymers were generated (>4 cycles).

Graphical abstract: Amphiphilic block copolymers featuring a reversible hetero Diels-Alder linkage

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Publication details

The article was received on 07 May 2014, accepted on 02 Jun 2014 and first published on 03 Jun 2014


Article type: Paper
DOI: 10.1039/C4PY00644E
Citation: Polym. Chem., 2014,5, 5330-5338
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    Amphiphilic block copolymers featuring a reversible hetero Diels-Alder linkage

    M. Langer, J. Brandt, A. Lederer, A. S. Goldmann, F. H. Schacher and C. Barner-Kowollik, Polym. Chem., 2014, 5, 5330
    DOI: 10.1039/C4PY00644E

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