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

Oektem G, Sahre K, Voit B, Jordan R, Kiriy A (2017)

Publication Type: Journal article

Publication year: 2017

Journal

Polymer Chemistry Royal Society of Chemistry

Book Volume: 8

Pages Range: 2675-2685

Journal Issue: 17

DOI: 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.

Involved external institutions

Leibniz-Institut für Polymerforschung Dresden e. V. DE Germany (DE) Technische Universität Dresden DE Germany (DE)

How to cite

APA:

Oektem, G., Sahre, K., Voit, B., Jordan, R., & Kiriy, A. (2017). Facile synthesis of oligo(3-hexylthiophene)s conductive wires with charge-transfer functions. Polymer Chemistry, 8(17), 2675-2685. https://doi.org/10.1039/c7py00428a

MLA:

Oektem, Goezde, et al. "Facile synthesis of oligo(3-hexylthiophene)s conductive wires with charge-transfer functions." Polymer Chemistry 8.17 (2017): 2675-2685.

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