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

Anna Isakova, Christian Burton, Daniel J. Nowakowski, Paul D. Topham

Research output: Contribution to journalArticle

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).
LanguageEnglish
Pages2796-2805
Number of pages10
JournalPolymer Chemistry
Volume8
Issue number18
Early online date11 Apr 2017
DOIs
Publication statusPublished - 14 May 2017

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Fullerenes
Cycloaddition
Cycloaddition Reaction
Molecular mass
Polymers
Polymerization
Derivatives
Photodynamic therapy
Photochemotherapy
Metals
Equipment and Supplies
Catalysts
Chemical analysis
fullerene C60

Cite this

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title = "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).",
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AU - Burton, Christian

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AU - Topham, Paul D.

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