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Facile synthesis of oligo(3-hexylthiophene)s conductive wires with charge-transfer functions

Reference

Gozde Oktem, Karin Sahre, Brigitte Voit, Rainer Jordan, Anton Kiriy, "Facile synthesis of oligo(3-hexylthiophene)s conductive wires with charge-transfer functions" , In Polym. Chem., The Royal Society of Chemistry, vol. 8, pp. 2675-2685, 2017. [doi]

Abstract

A series of fully conjugated oligo(3-hexylthiophene)s bearing different starting- and end-groups have been synthesized by means of externally initiated Kumada catalyst-transfer polymerization (KCTP) and Grignard Metathesis Polymerization (GRIM). These kinds of oligomers' starting- and end-groups include tert-butyl protected thiols to be used for binding of oligomers to gold electrodes and tetracyanobutadiene-based donor-acceptor (DA) end-groups, such as dimethylaniline-tetracyanobutadiene (DMA-TCBD) and ferrocene-tetracyanobutadiene (Fc-TCBD), introduced to control the charge transport through the oligomers. The DMA-TCBD and Fc-TCBD end groups were incorporated by means of a Diederich-type click transformation of appropriately end-terminated oligo(3-hexylthiophene)s. The efficiency of the end-group functionalization was comprehensively assessed by NMR spectroscopy and MALDI-TOF spectrometry whereas the redox activities of the DA end-groups were examined by cyclic voltammetry. KCTP showed a much superior performance compared to GRIM in the introduction of a desirable end-group functionality. The thus-prepared conjugated oligomers are attractive materials for application in molecular electronics which will be explored in future studies.

Bibtex

@Article{C7PY00428A,
author ="Oktem, Gozde and Sahre, Karin and Voit, Brigitte and Jordan, Rainer and Kiriy, Anton",
title ="Facile synthesis of oligo(3-hexylthiophene)s conductive wires with charge-transfer functions",
journal ="Polym. Chem.",
year ="2017",
volume ="8",
issue ="17",
pages ="2675-2685",
publisher ="The Royal Society of Chemistry",
doi ="10.1039/C7PY00428A",
url ="http://dx.doi.org/10.1039/C7PY00428A",
abstract ="A series of fully conjugated oligo(3-hexylthiophene)s bearing different starting- and end-groups have been synthesized by means of externally initiated Kumada catalyst-transfer polymerization (KCTP) and Grignard Metathesis Polymerization (GRIM). These kinds of oligomers{'} starting- and end-groups include tert-butyl protected thiols to be used for binding of oligomers to gold electrodes and tetracyanobutadiene-based donor-acceptor (DA) end-groups{,} such as dimethylaniline-tetracyanobutadiene (DMA-TCBD) and ferrocene-tetracyanobutadiene (Fc-TCBD){,} introduced to control the charge transport through the oligomers. The DMA-TCBD and Fc-TCBD end groups were incorporated by means of a Diederich-type click transformation of appropriately end-terminated oligo(3-hexylthiophene)s. The efficiency of the end-group functionalization was comprehensively assessed by NMR spectroscopy and MALDI-TOF spectrometry whereas the redox activities of the DA end-groups were examined by cyclic voltammetry. KCTP showed a much superior performance compared to GRIM in the introduction of a desirable end-group functionality. The thus-prepared conjugated oligomers are attractive materials for application in molecular electronics which will be explored in future studies."}

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Related Paths

Biomolecular-Assembled Circuits Path, Organic / Polymer Path

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