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Conducting polymer/SWCNTs modular hybrid materials via Diels-Alder ligation

  • The development of a facile covalent strategy for the fabrication of organic conducting polymers (OCPs)/carbon nanotubes (CNTs) based molecular hybrid materials remains a challenge and is expected to address the detrimental intrinsic bundling issue of CNTs. In view of the pristine CNTs' ability to undergo Diels–Alder reactions with dienes, we report the synthesis of a novel poly(3-hexylthiophene) (P3HT) based organic conducting polymer (OCP) with terminal cyclopentadienyl (Cp) groups. The synthetic strategy employed is based on a combination of in situ end group functionalization via Grignard metathesis (GRIM) polymerization and a subsequent end group switching via reaction with nickelocene. Characterization data from Matrix-assisted laser desorption-ionization time-of-flight mass spectrometry (MALDI–TOF MS) fully support the successful synthesis of monofunctional Cp-capped P3HT, which was found to be highly reactive toward dienophile end-capped polystyrene (PS). The Cp-capped P3HT wasThe development of a facile covalent strategy for the fabrication of organic conducting polymers (OCPs)/carbon nanotubes (CNTs) based molecular hybrid materials remains a challenge and is expected to address the detrimental intrinsic bundling issue of CNTs. In view of the pristine CNTs' ability to undergo Diels–Alder reactions with dienes, we report the synthesis of a novel poly(3-hexylthiophene) (P3HT) based organic conducting polymer (OCP) with terminal cyclopentadienyl (Cp) groups. The synthetic strategy employed is based on a combination of in situ end group functionalization via Grignard metathesis (GRIM) polymerization and a subsequent end group switching via reaction with nickelocene. Characterization data from Matrix-assisted laser desorption-ionization time-of-flight mass spectrometry (MALDI–TOF MS) fully support the successful synthesis of monofunctional Cp-capped P3HT, which was found to be highly reactive toward dienophile end-capped polystyrene (PS). The Cp-capped P3HT was subsequently ligated to the surface of pristine single walled CNTs (SWCNTs). The resulting P3HT/SWCNTs molecular hybrid material was characterized using thermogravimetric analysis (TGA), elemental analysis (EA), X-ray photoelectron spectroscopy (XPS), and high resolution transmission electron microscopy (HRTEM). The data from TGA, EA, and XPS were used to quantitatively deduce the grafting density. P3HT/SWCNTs prepared with Cp capped P3HT was found to contain 2 times more P3HT than the reference sample, featuring a grafting density of 0.0510 chains·nm–2 and a periodicity of 1 P3HT chain per 748 carbon atoms of the SWCNTs. HRTEM revealed individual SWCNTs wrapped with P3HT whereas in the reference sample P3HT was adsorbed on the bundles of the SWCNTs. The results presented here provide a new avenue for designing novel materials based on CNTs and OCPs.zeige mehrzeige weniger

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Metadaten
Autoren/innen:B. Yameen, N. Zydziak, Steffen Weidner, M. Bruns, C. Barner-Kowollik
Dokumenttyp:Zeitschriftenartikel
Veröffentlichungsform:Verlagsliteratur
Sprache:Englisch
Titel des übergeordneten Werkes (Englisch):Macromolecules
Jahr der Erstveröffentlichung:2013
Organisationseinheit der BAM:1 Analytische Chemie; Referenzmaterialien
1 Analytische Chemie; Referenzmaterialien / 1.3 Strukturanalytik
Verlag:American Chemical Society
Verlagsort:Washington, DC
Jahrgang/Band:46
Ausgabe/Heft:7
Erste Seite:2606
Letzte Seite:2615
Freie Schlagwörter:Mass spectrometry; Polymers
DOI:https://doi.org/10.1021/ma4004055
ISSN:0024-9297
ISSN:1520-5835
Verfügbarkeit des Dokuments:Datei im Netzwerk der BAM verfügbar ("Closed Access")
Datum der Freischaltung:20.02.2016
Referierte Publikation:Ja
Datum der Eintragung als referierte Publikation:30.05.2013