Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives

Christian Ruzie, Jolanta Karpinska, Anne Laurent, Lionel Sanguinet, Simon Hunter, Thomas D. Anthopoulos, Vincent Lemaur, Jérôme Cornil, Alan R. Kennedy, Oliver Fenwick, Paolo Samori, Guillaume Schweicher, Basab Chattopadhyay, Yves Henri Geerts

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Abstract

Five new molecular semiconductors that differ from dioctylbenzothienobenzothiophene, by the introduction of ether or thioether side chains, have been synthesized and obtained in good yields. Their availability in sufficient quantities has allowed investigation of their electrochemical behaviour in solution and their electronic properties in solid state. Both ether and thioether compounds oxidise rather easily in solution, but nevertheless, they exhibit rather high ionisation potentials. This is a consequence of their crystal structure. Dioctylthioetherbenzothienobenzothiophene is rather sensitive to oxidation and degrades easily in close to ambient conditions. Dioctylletherbenzothienobenzothiophene is more stable. Its charge carrier mobility remains however rather moderate, on the order of 0.5 cm2/V.s, whereas that of dioctylbenzothienobenzothiophene reached 4 cm2/V.s, in the same conditions. The difference is explained by intrinsic factors as shown by a theoretical modelling.
Original languageEnglish
JournalJournal of Materials Chemistry. C
Early online date5 May 2016
DOIs
Publication statusE-pub ahead of print - 5 May 2016

Fingerprint

Ionization potential
Chemical stability
Sulfides
Ether
Cyclic voltammetry
Charge transfer
Ethers
Derivatives
Intrinsic Factor
Carrier mobility
Charge carriers
Electronic properties
Crystal structure
Availability
Semiconductor materials
Oxidation
benzothiophene

Keywords

  • molecular semiconductors
  • dioctylthioetherbenzothienobenzothiophene
  • chemical stability

Cite this

Ruzie, Christian ; Karpinska, Jolanta ; Laurent, Anne ; Sanguinet, Lionel ; Hunter, Simon ; Anthopoulos, Thomas D. ; Lemaur, Vincent ; Cornil, Jérôme ; Kennedy, Alan R. ; Fenwick, Oliver ; Samori, Paolo ; Schweicher, Guillaume ; Chattopadhyay, Basab ; Geerts, Yves Henri. / Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives. In: Journal of Materials Chemistry. C . 2016.
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abstract = "Five new molecular semiconductors that differ from dioctylbenzothienobenzothiophene, by the introduction of ether or thioether side chains, have been synthesized and obtained in good yields. Their availability in sufficient quantities has allowed investigation of their electrochemical behaviour in solution and their electronic properties in solid state. Both ether and thioether compounds oxidise rather easily in solution, but nevertheless, they exhibit rather high ionisation potentials. This is a consequence of their crystal structure. Dioctylthioetherbenzothienobenzothiophene is rather sensitive to oxidation and degrades easily in close to ambient conditions. Dioctylletherbenzothienobenzothiophene is more stable. Its charge carrier mobility remains however rather moderate, on the order of 0.5 cm2/V.s, whereas that of dioctylbenzothienobenzothiophene reached 4 cm2/V.s, in the same conditions. The difference is explained by intrinsic factors as shown by a theoretical modelling.",
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Ruzie, C, Karpinska, J, Laurent, A, Sanguinet, L, Hunter, S, Anthopoulos, TD, Lemaur, V, Cornil, J, Kennedy, AR, Fenwick, O, Samori, P, Schweicher, G, Chattopadhyay, B & Geerts, YH 2016, 'Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives', Journal of Materials Chemistry. C . https://doi.org/10.1039/C6TC01409G

Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives. / Ruzie, Christian ; Karpinska, Jolanta; Laurent, Anne; Sanguinet, Lionel; Hunter, Simon; Anthopoulos, Thomas D.; Lemaur, Vincent; Cornil, Jérôme; Kennedy, Alan R.; Fenwick, Oliver; Samori, Paolo; Schweicher, Guillaume; Chattopadhyay, Basab; Geerts, Yves Henri.

In: Journal of Materials Chemistry. C , 05.05.2016.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives

AU - Ruzie, Christian

AU - Karpinska, Jolanta

AU - Laurent, Anne

AU - Sanguinet, Lionel

AU - Hunter, Simon

AU - Anthopoulos, Thomas D.

AU - Lemaur, Vincent

AU - Cornil, Jérôme

AU - Kennedy, Alan R.

AU - Fenwick, Oliver

AU - Samori, Paolo

AU - Schweicher, Guillaume

AU - Chattopadhyay, Basab

AU - Geerts, Yves Henri

PY - 2016/5/5

Y1 - 2016/5/5

N2 - Five new molecular semiconductors that differ from dioctylbenzothienobenzothiophene, by the introduction of ether or thioether side chains, have been synthesized and obtained in good yields. Their availability in sufficient quantities has allowed investigation of their electrochemical behaviour in solution and their electronic properties in solid state. Both ether and thioether compounds oxidise rather easily in solution, but nevertheless, they exhibit rather high ionisation potentials. This is a consequence of their crystal structure. Dioctylthioetherbenzothienobenzothiophene is rather sensitive to oxidation and degrades easily in close to ambient conditions. Dioctylletherbenzothienobenzothiophene is more stable. Its charge carrier mobility remains however rather moderate, on the order of 0.5 cm2/V.s, whereas that of dioctylbenzothienobenzothiophene reached 4 cm2/V.s, in the same conditions. The difference is explained by intrinsic factors as shown by a theoretical modelling.

AB - Five new molecular semiconductors that differ from dioctylbenzothienobenzothiophene, by the introduction of ether or thioether side chains, have been synthesized and obtained in good yields. Their availability in sufficient quantities has allowed investigation of their electrochemical behaviour in solution and their electronic properties in solid state. Both ether and thioether compounds oxidise rather easily in solution, but nevertheless, they exhibit rather high ionisation potentials. This is a consequence of their crystal structure. Dioctylthioetherbenzothienobenzothiophene is rather sensitive to oxidation and degrades easily in close to ambient conditions. Dioctylletherbenzothienobenzothiophene is more stable. Its charge carrier mobility remains however rather moderate, on the order of 0.5 cm2/V.s, whereas that of dioctylbenzothienobenzothiophene reached 4 cm2/V.s, in the same conditions. The difference is explained by intrinsic factors as shown by a theoretical modelling.

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KW - chemical stability

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JO - Journal of Materials Chemistry. C

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SN - 2050-7526

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