TY - JOUR
T1 - Diels–Alder cycloaddition and RAFT chain end functionality:
T2 - an elegant route to fullerene end-capped polymers with control over molecular mass and architecture
AU - Isakova, Anna
AU - Burton, Christian
AU - Nowakowski, Daniel J.
AU - Topham, Paul D.
PY - 2017/5/14
Y1 - 2017/5/14
N2 - 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).
AB - 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).
UR - http://pubs.rsc.org/en/Content/ArticleLanding/2017/PY/C7PY00394C#!divAbstract
UR - http://www.scopus.com/inward/record.url?scp=85021822707&partnerID=8YFLogxK
U2 - 10.1039/C7PY00394C
DO - 10.1039/C7PY00394C
M3 - Article
SN - 1759-9954
VL - 8
SP - 2796
EP - 2805
JO - Polymer Chemistry
JF - Polymer Chemistry
IS - 18
ER -