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Issue 17, 2017
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Facile synthesis of oligo(3-hexylthiophene)s conductive wires with charge-transfer functions

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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.

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

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Publication details

The article was received on 13 Mar 2017, accepted on 31 Mar 2017 and first published on 31 Mar 2017


Article type: Paper
DOI: 10.1039/C7PY00428A
Citation: Polym. Chem., 2017,8, 2675-2685
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    Facile synthesis of oligo(3-hexylthiophene)s conductive wires with charge-transfer functions

    G. Öktem, K. Sahre, B. Voit, R. Jordan and A. Kiriy, Polym. Chem., 2017, 8, 2675
    DOI: 10.1039/C7PY00428A

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