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

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).

Publication DOI: https://doi.org/10.1039/C7PY00394C
Divisions: College of Engineering & Physical Sciences
College of Engineering & Physical Sciences > Chemical Engineering & Applied Chemistry
College of Engineering & Physical Sciences > Aston Institute of Materials Research (AIMR)
College of Engineering & Physical Sciences > Energy and Bioproducts Research Institute (EBRI)
Uncontrolled Keywords: Bioengineering,Biochemistry,Biomedical Engineering,Polymers and Plastics,Organic Chemistry
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Related URLs: http://www.scop ... tnerID=8YFLogxK (Scopus URL)
PURE Output Type: Article
Published Date: 2017-05-14
Published Online Date: 2017-04-11
Accepted Date: 2017-04-11
Submitted Date: 2017-03-08
Authors: Isakova, Anna
Burton, Christian
Nowakowski, Daniel J. (ORCID Profile 0000-0001-8056-5316)
Topham, Paul D. (ORCID Profile 0000-0003-4152-6976)

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