π-conjugated polymer-fullerene covalent hybrids via ambient conditions Diels-Alder ligation

Yameen, B., Puerckhauer, T., Ludwig, J., Ahmed, I., Altintas, O., Fruk, L., Colsmann, A., & Barner-Kowollik, C. (2014) π-conjugated polymer-fullerene covalent hybrids via ambient conditions Diels-Alder ligation. Small, 10(15).

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Abstract

The established ability of graphitic carbon-nanomaterials to undergo ambient condition Diels-Alder reactions with cyclopentadienyl (Cp) groups is herein employed to prepare fullerene-polythiophene covalent hybrids with improved electron transfer and film forming characteristics. A novel precisely designed polythiophene (M n 9.8 kD, D strok sign 1.4) with 17 mol% of Cp-groups bearing repeat unit is prepared via Grignard metathesis polymerization. The UV/Vis absorption and fluorescence (λex 450 nm) characteristics of polythiophene with pendant Cp-groups (λmax 447 nm, λe-max 576 nm) are comparable to the reference poly(3-hexylthiophene) (λmax 450 nm, λe-max 576 nm). The novel polythiophene with pendant Cp-groups is capable of producing solvent-stable free-standing polythiophene films, and non-solvent assisted self-assemblies resulting in solvent-stable nanoporous-microstructures. 1H-NMR spectroscopy reveals an efficient reaction of the pendant Cp-groups with C60. The UV/Vis spectroscopic analyses of solution and thin films of the covalent and physical hybrids disclose closer donor-acceptor packing in the case of covalent hybrids. AFM images evidence that the covalent hybrids form smooth films with finer lamellar-organization. The effect is particularly remarkable in the case of poorly soluble C60. A significant enhancement in photo-voltage is observed for all devices constituted of covalent hybrids, highlighting novel avenues to developing efficient electron donor-acceptor combinations for light harvesting systems. Fullerene-polythiophene covalent-hybrids are achieved by exploiting the natural ability of pristine carbon nanomaterials to undergo ambient condition Diels-Alder reactions with cyclopentadienyl (Cp) groups. A novel polythiophene with pendant Cp-groups prepared via GRIM polymerization is employed to fabricate these covalent-hybrids that exhibit a higher extent of fluorescence quenching and smoother films with fine lamellar texture compared to physical hybrids. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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ID Code: 99417
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :5
Export Date: 5 September 2016
CODEN: SMALB
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76128 Karlsruhe, Germany; email: christopher.barner-kowollik@kit.edu
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Keywords: covalent nanohybrids, Diels-Alder ligation, fullerenes, polythiophene, Nanostructured materials, Nuclear magnetic resonance spectroscopy, Polymerization, Solvents, Spectroscopic analysis, Diels-Alder, Electron donor acceptors, Fluorescence quenching, Grignard metathesis polymerizations, Light-harvesting systems, Nanohybrids, Poly (3-hexylthiophene), Poly-thiophene, Film preparation
DOI: 10.1002/smll.201303772
ISSN: 16136810
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 27 Sep 2016 00:45

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