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. 2019 Feb 18;11(2):355.
doi: 10.3390/polym11020355.

The Different Outcomes of Electrochemical Copolymerisation: 3-Hexylthiophene with Indole, Carbazole or Fluorene

Karolina Gebka  1 , Tomasz Jarosz  2   3 , Agnieszka Stolarczyk  4
Affiliations

The Different Outcomes of Electrochemical Copolymerisation: 3-Hexylthiophene with Indole, Carbazole or Fluorene

Karolina Gebka et al. Polymers (Basel). .

Abstract

Electrochemical polymerisation is reported to be a method for readily producing copolymers of various conjugated molecules. We employed this method for mixtures of indole, carbazole or fluorene with 3-hexylthiophene (HT), in order to obtain their soluble copolymers. Although polymer films were obtained, infrared (IR) and Raman investigations showed that instead of the expected linear copolymers, polyindole and polycarbazole N-substituted with HT, as well as a poly(3-hexylthiophene) (PHT)/polyfluorene blend were produced instead. Boron trifluoride diethyl etherate was also used in an attempt to promote copolymerisation, but the produced deposits were found to be highly degraded.

Keywords: carbazole; electrochemical copolymerisation; fluorene; indole; poly(3-hexylthiophene).

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure A1
Figure A1
CV recorded during the electrochemical polymerisation of 20 mM HT in 0.1 M tetrabutylammonium tetrafluoroborate.
Figure A2
Figure A2
IR spectrum of the polymer fraction of Fl-HT EP soluble in chloroform and deposited from solution on the IR spectrometer ATR crystal.
Figure A3
Figure A3
Raman spectra of the polymer films obtained during electrochemical polymerisation of In-HT, Cz-HT and Fl-HT.
Figure A4
Figure A4
Electrochemical polymerisation of In-HT (a), Cz-HT (b), Fl-HT (c) containing 10 vol % boron trifluoride diethyl etherate.
Figure A5
Figure A5
IR spectra of the polymer deposits obtained during electrochemical polymerisation of In-HT, Cz-HT and Fl-HT in the presence of 10 vol % boron trifluoride diethyl etherate.
Figure A6
Figure A6
Raman spectra of the polymer deposits obtained during electrochemical polymerisation of In-HT, Cz-HT and Fl-HT in the presence of 10 vol % boron trifluoride diethyl etherate.
Scheme 1
Scheme 1
Chemical formulae of the co-monomers investigated.
Figure 1
Figure 1
Electrochemical polymerisation of indole (a), CV of the deposited layer (b).
Figure 2
Figure 2
Electrochemical polymerisation of In-HT 5:2 (a), In-HT 1:10 (b), CVs of deposited In-HT 5:2 EP (c), In-HT 1:10 EP (d) layers.
Figure 3
Figure 3
Electrochemical polymerisation of carbazole (a), CV of the deposited layer (b).
Figure 4
Figure 4
Electrochemical polymerisation of Cz-HT 5:1 (a), Cz-HT 1:5 (b), CVs of deposited Cz-HT 5:1 EP (c), Cz-HT 1:5 EP (d) layers.
Figure 5
Figure 5
Electrochemical polymerisation of fluorene (a), CV of the deposited layer (b).
Figure 6
Figure 6
Electrochemical polymerisation of Fl-HT 5:1 (a), Fl-HT 1:5 (b), CVs of deposited Fl-HT 5:1 EP (c), Fl-HT 1:5 EP (d) layers.
Figure 7
Figure 7
Attenuated total reflection-infrared (ATR-IR) spectra of indole, its homopolymer (In EP) layer and In-HT EP layers.
Figure 8
Figure 8
ATR-IR spectra of carbazole, its homopolymer (Cz EP) layer and Cz-HT EP layers.
Figure 9
Figure 9
ATR-IR spectra of the fluorene, its homopolymer (Fl EP) layer and Fl-HT EP layers.
Scheme 2
Scheme 2
Proposed structural formulae for In-HT EP and for Cz-HT EP.
Figure 10
Figure 10
Ultraviolet-visible-near infrared (UV-Vis) spectra of polymeric films prepared from pure monomer solutions (a) and monomer solutions containing HT (b).
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