Functionalized dithienylthiazolo[5, 4-d]thiazoles for solution-processable organic field-effect transistors

S. Van Mierloo, K. Vasseur, N. Van Den Brande, A.E. Boyukbayram, B. Ruttens, S.D. Rodriguez, E. Botek, V. Liégeois, J. D'Haen, P.J. Adriaensens, P. Heremans, B. Champagne, G. Van Assche, L. Lutsen, D.J. Vanderzande, W. Maes

Research output: Contribution to journalArticle

Abstract

A series of 5′-aryl-substituted 2, 5-bis(3′-hexylthiophen- 2′-yl)thiazolo[5, 4-d]thiazole derivatives was synthesized and these expanded semiconductors were investigated as active materials for solution-processable organic field-effect transistors. Field-effect mobilities of up to 10 cm V s were obtained, representing the first reasonable FET behavior for highly soluble thiazolo[5, 4-d]thiazole-based small organic compounds suitable for printable electronics. Thermal and electrooptical material properties were studied by thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and UV/Vis spectroscopy. Trends in thermal and optical data were supported by (time-dependent) density functional theory calculations. Additional X-ray diffraction, atomic force microscopy, and scanning electron microscopy studies provided insight in the relationship between the molecular structures, film morphologies, and FET performances. The fibrillar microcrystalline structure observed for the best-performing thienyl-substituted material was linked to the high mobility.
Original languageEnglish
Pages (from-to)923-930
Number of pages8
JournalChemPlusChem
Volume77
Issue number10
DOIs
Publication statusPublished - 1 Oct 2012

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Thiazoles
Organic field effect transistors
Field effect transistors
Electrooptical materials
Ultraviolet spectroscopy
Organic compounds
Molecular structure
Cyclic voltammetry
Density functional theory
Thermogravimetric analysis
Differential scanning calorimetry
Atomic force microscopy
Materials properties
Electronic equipment
Semiconductor materials
Derivatives
X ray diffraction
Scanning electron microscopy
dithienylthiazolo(5,4-d)thiazole
Hot Temperature

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Van Mierloo, S., Vasseur, K., Van Den Brande, N., Boyukbayram, A. E., Ruttens, B., Rodriguez, S. D., ... Maes, W. (2012). Functionalized dithienylthiazolo[5, 4-d]thiazoles for solution-processable organic field-effect transistors. ChemPlusChem, 77(10), 923-930. https://doi.org/10.1002/cplu.201200132
Van Mierloo, S. ; Vasseur, K. ; Van Den Brande, N. ; Boyukbayram, A.E. ; Ruttens, B. ; Rodriguez, S.D. ; Botek, E. ; Liégeois, V. ; D'Haen, J. ; Adriaensens, P.J. ; Heremans, P. ; Champagne, B. ; Van Assche, G. ; Lutsen, L. ; Vanderzande, D.J. ; Maes, W. / Functionalized dithienylthiazolo[5, 4-d]thiazoles for solution-processable organic field-effect transistors. In: ChemPlusChem. 2012 ; Vol. 77, No. 10. pp. 923-930.
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abstract = "A series of 5′-aryl-substituted 2, 5-bis(3′-hexylthiophen- 2′-yl)thiazolo[5, 4-d]thiazole derivatives was synthesized and these expanded semiconductors were investigated as active materials for solution-processable organic field-effect transistors. Field-effect mobilities of up to 10 cm V s were obtained, representing the first reasonable FET behavior for highly soluble thiazolo[5, 4-d]thiazole-based small organic compounds suitable for printable electronics. Thermal and electrooptical material properties were studied by thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and UV/Vis spectroscopy. Trends in thermal and optical data were supported by (time-dependent) density functional theory calculations. Additional X-ray diffraction, atomic force microscopy, and scanning electron microscopy studies provided insight in the relationship between the molecular structures, film morphologies, and FET performances. The fibrillar microcrystalline structure observed for the best-performing thienyl-substituted material was linked to the high mobility.",
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Van Mierloo, S, Vasseur, K, Van Den Brande, N, Boyukbayram, AE, Ruttens, B, Rodriguez, SD, Botek, E, Liégeois, V, D'Haen, J, Adriaensens, PJ, Heremans, P, Champagne, B, Van Assche, G, Lutsen, L, Vanderzande, DJ & Maes, W 2012, 'Functionalized dithienylthiazolo[5, 4-d]thiazoles for solution-processable organic field-effect transistors', ChemPlusChem, vol. 77, no. 10, pp. 923-930. https://doi.org/10.1002/cplu.201200132

Functionalized dithienylthiazolo[5, 4-d]thiazoles for solution-processable organic field-effect transistors. / Van Mierloo, S.; Vasseur, K.; Van Den Brande, N.; Boyukbayram, A.E.; Ruttens, B.; Rodriguez, S.D.; Botek, E.; Liégeois, V.; D'Haen, J.; Adriaensens, P.J.; Heremans, P.; Champagne, B.; Van Assche, G.; Lutsen, L.; Vanderzande, D.J.; Maes, W.

In: ChemPlusChem, Vol. 77, No. 10, 01.10.2012, p. 923-930.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Functionalized dithienylthiazolo[5, 4-d]thiazoles for solution-processable organic field-effect transistors

AU - Van Mierloo, S.

AU - Vasseur, K.

AU - Van Den Brande, N.

AU - Boyukbayram, A.E.

AU - Ruttens, B.

AU - Rodriguez, S.D.

AU - Botek, E.

AU - Liégeois, V.

AU - D'Haen, J.

AU - Adriaensens, P.J.

AU - Heremans, P.

AU - Champagne, B.

AU - Van Assche, G.

AU - Lutsen, L.

AU - Vanderzande, D.J.

AU - Maes, W.

N1 - Copyright 2012 Elsevier B.V., All rights reserved.

PY - 2012/10/1

Y1 - 2012/10/1

N2 - A series of 5′-aryl-substituted 2, 5-bis(3′-hexylthiophen- 2′-yl)thiazolo[5, 4-d]thiazole derivatives was synthesized and these expanded semiconductors were investigated as active materials for solution-processable organic field-effect transistors. Field-effect mobilities of up to 10 cm V s were obtained, representing the first reasonable FET behavior for highly soluble thiazolo[5, 4-d]thiazole-based small organic compounds suitable for printable electronics. Thermal and electrooptical material properties were studied by thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and UV/Vis spectroscopy. Trends in thermal and optical data were supported by (time-dependent) density functional theory calculations. Additional X-ray diffraction, atomic force microscopy, and scanning electron microscopy studies provided insight in the relationship between the molecular structures, film morphologies, and FET performances. The fibrillar microcrystalline structure observed for the best-performing thienyl-substituted material was linked to the high mobility.

AB - A series of 5′-aryl-substituted 2, 5-bis(3′-hexylthiophen- 2′-yl)thiazolo[5, 4-d]thiazole derivatives was synthesized and these expanded semiconductors were investigated as active materials for solution-processable organic field-effect transistors. Field-effect mobilities of up to 10 cm V s were obtained, representing the first reasonable FET behavior for highly soluble thiazolo[5, 4-d]thiazole-based small organic compounds suitable for printable electronics. Thermal and electrooptical material properties were studied by thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and UV/Vis spectroscopy. Trends in thermal and optical data were supported by (time-dependent) density functional theory calculations. Additional X-ray diffraction, atomic force microscopy, and scanning electron microscopy studies provided insight in the relationship between the molecular structures, film morphologies, and FET performances. The fibrillar microcrystalline structure observed for the best-performing thienyl-substituted material was linked to the high mobility.

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U2 - 10.1002/cplu.201200132

DO - 10.1002/cplu.201200132

M3 - Article

VL - 77

SP - 923

EP - 930

JO - ChemPlusChem

JF - ChemPlusChem

SN - 2192-6506

IS - 10

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