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Issue 7, 2015
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Synthesis and characterization of branched fullerene-terminated poly(ethylene glycol)s

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Abstract

Poly(ethylene glycol) [1, PEG∼4(OH)2, Mn ∼ 200], glycerol ethoxylate [2, PEG∼21(OH)3, Mn ∼ 1000] and pentaerythritol ethoxylate [3, PEG∼15(OH)4, Mn ∼ 797] react directly with phenyl-C61-butyric acid methyl ester (PCBM), in the presence of dibutyltinoxide (DBTO) catalyst at 140 °C, to give a mixture of fullerene [C60] end-capped PEGs via transesterification. Among these PEG linkers, only PEG∼4(OPCB)2 (4a) (OPCB: ester oxygen linked phenyl-C61-butyryl group) was successfully isolated from the crude product mixture in the fully end-capped form. Fully acylated PEG∼21(OPCB)3 (5) and PEG∼15(OPCB)4 (6) could not be separated chromatographically from incompletely reacted species due to the polydispersity in branch lengths. This purification challenge was overcome by using a monodisperse branched core, 1,3,5-tris(octagoloxymethyl)benzene [7, PEG24(OH)3] to give a monodisperse tris-fullerene homostar, PEG24(OPCB)3 (8). The structures of the bis- and tris-fullerene products were confirmed by MALDI-TOF mass spectrometry and 1H NMR spectroscopy with supporting FTIR and UV-vis spectroscopic analysis.

Graphical abstract: Synthesis and characterization of branched fullerene-terminated poly(ethylene glycol)s

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Supplementary files

Article information


Submitted
22 Aug 2014
Accepted
07 Nov 2014
First published
07 Nov 2014

This article is Open Access

Polym. Chem., 2015,6, 1056-1065
Article type
Paper
Author version available

Synthesis and characterization of branched fullerene-terminated poly(ethylene glycol)s

H. C. Yau, M. K. Bayazit, P. R. J. Gaffney, A. G. Livingston, J. H. G. Steinke and M. S. P. Shaffer, Polym. Chem., 2015, 6, 1056
DOI: 10.1039/C4PY01167H

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