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Issue 18, 2017
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Diels–Alder cycloaddition and RAFT chain end functionality: an elegant route to fullerene end-capped polymers with control over molecular mass and architecture

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Abstract

Fullerene C60 functionalised polymers (FFPs) have found numerous applications from photovoltaic devices to materials for photodynamic therapy. Polymer end-capping is one way to fabricate FFPs since it provides enhanced control over the macromolecular architecture and composition. This paper reports, for the first time, a facile, metal catalyst-free approach to FFPs where polymers, generated by reversible-addition fragmentation chain transfer (RAFT) polymerisation, were coupled to a fullerene derivative through chain-end functionality, provided by the chain transfer agent without further modification. Two routes to a fullerene derivative were compared – based on the Prato reaction and Diels–Alder cycloaddition. The Diels–Alder route exclusively yielded the mono-addition product, whereas the Prato route resulted in a mixture of mono- and diadducts which required further separation. This elegant combination of well-defined RAFT polymerisation and precise Diels–Alder addition allowed one to obtain fullerene end-capped polymers within a wide range of molecular masses (from 5000 to 50 000 g mol−1).

Graphical abstract: Diels–Alder cycloaddition and RAFT chain end functionality: an elegant route to fullerene end-capped polymers with control over molecular mass and architecture

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Publication details

The article was received on 08 Mar 2017, accepted on 11 Apr 2017 and first published on 11 Apr 2017


Article type: Paper
DOI: 10.1039/C7PY00394C
Citation: Polym. Chem., 2017,8, 2796-2805
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    Diels–Alder cycloaddition and RAFT chain end functionality: an elegant route to fullerene end-capped polymers with control over molecular mass and architecture

    A. Isakova, C. Burton, D. J. Nowakowski and P. D. Topham, Polym. Chem., 2017, 8, 2796
    DOI: 10.1039/C7PY00394C

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