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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

Lookup NU author(s): Dr Anna Isakova

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Abstract

© 2017 The Royal Society of Chemistry. 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 50000 g mol-1).

Publication metadata

Author(s): Isakova A, Burton C, Nowakowski DJ, Topham PD

Publication type: Article

Publication status: Published

Journal: Polymer Chemistry

Year: 2017

Volume: 8

Issue: 18

Pages: 2796-2805

Print publication date: 14/05/2017

Online publication date: 11/04/2017

Acceptance date: 11/04/2017

ISSN (print): 1759-9954

ISSN (electronic): 1759-9962

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/C7PY00394C

DOI: 10.1039/c7py00394c

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