R. Hiorns, É. Cloutet, E. Ibarboure
Apr 16, 2009
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0
Influential Citations
38
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Journal
Macromolecules
Abstract
A prototype for a new class of macromolecules with a high fraction of fullerene is proposed. Their facile synthesis, modular structure, electronic activity, and novel solid-state behavior make them promising materials for photovoltaic applications. Controlled reversible-deactivation radical additions of the sterically bulky 1,4-bis(methylcyclohexyl ether)-2,5-dibromomethyl benzene to fullerene are indicated by GPC, NMR, and TGA studies to yield oligomers and polymers containing C60 in the main chain. UV and cyclic voltammetry indicate that the C60 undergoes mainly 1,4-additions and a minority (ca. 20%) of 1,2-additions to make a regio-irregular macromolecule. The same reaction performed in the presence of 1,4-bis(methylcyclohexyl ether)-2-bromomethyl benzene, resulting in macromolecules with bromomethyl-free chain ends, permitted confirmation of the aforementioned characteristics. The unusual reptation of the poly{(1,4-fullerene)-alt-[1,4-dimethylene-2,5-bis(cyclohexylmethyl ether)phenylene]}s (PFDP) in a...