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Issue 5, 2010
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Poly(3-hexylthiophene) bearing pendant fullerenes: aggregation vs. self-organization

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Abstract

Novel graft copolymers are reported based on poly(3-hexylthiophene) (P3HT) bearing side chains of poly(styrene-stat-chloromethylstyrene), onto which a fullerene C60 or PCBM is covalently attached. P3HT was brominated at the 4-position to various extents (1–30 mol%), subsequently Suzuki-coupled with the boronic ester of 1-(4′-bromophenyl)-1-(2″,2″,6″,6″-tetramethyl-1-piperidinyloxy)ethyl (tempo) to form a nitroxide-functionalized P3HT macroinitiator, which was then used to initiate the nitroxide-mediated radical polymerization (NMRP) of chloromethylstyrene (CMS)-stat-styrene (ST) side chains. CMS units were functionalized with azide units and used to attach fullerene. The polymers contained a relatively high mass content of fullerene (20–41 wt%). Photoluminescence of P3HT is strongly quenched by the fullerene. The absorption of P3HT maximum shifts toward shorter wavelengths with increasing graft density. Films of PCBM/C60 graft copolymers form a bicontinuous morphology with feature sizes <5 nm. Grafting fullerene-bearing side chains directly to P3HT is found to reduce the semi-crystallinity of the P3HT domains, reduce the hole charge mobility, and significantly reduce their photovoltaic activity. This is believed to be due to the poorer solubility of the fullerene units relative to the polymer chains which aggregate during film casting and restricts self-organization of the conjugated polymer.

Graphical abstract: Poly(3-hexylthiophene) bearing pendant fullerenes: aggregation vs. self-organization

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Publication details

The article was received on 20 Dec 2009, accepted on 26 Jan 2010, published on 25 Feb 2010 and first published online on 25 Feb 2010


Article type: Paper
DOI: 10.1039/B9PY00384C
Citation: Polym. Chem., 2010,1, 708-719
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    Poly(3-hexylthiophene) bearing pendant fullerenes: aggregation vs. self-organization

    B. Gholamkhass, T. J. Peckham and S. Holdcroft, Polym. Chem., 2010, 1, 708
    DOI: 10.1039/B9PY00384C

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