Issue 15, 2010
From the journal:

Physical Chemistry Chemical Physics

Acetylenic spacers in phenylene end-substituted oligothiophene core for highly air-stable organic field-effect transistors†

Abdou Karim Diallo,a   Christine Videlot-Ackermann,*a   Philippe Marsal,a   Hugues Brisset,a   Frédéric Fages,a   Atsufumi Kumagai,b   Noriyuki Yoshimoto,b   Françoise Serein-Spirau*c  and  Jean-Pierre Lère-Portec  

* Corresponding authors

a Centre Interdisciplinaire de Nanoscience de Marseille (CINaM), CNRS UPR 3118, Campus Luminy, Aix Marseille Université, Case 913, 13288 Marseille Cedex 09, France
E-mail: videlot@cinam.univ-mrs.fr
Fax: +33 4 91 82 95 80
Tel: +33 6 17 24 81 93

b Graduate School of Engineering, Iwate University, 4-3-5 Ueda, Morioka 020-8551, Japan
E-mail: yoshimoto@iwate.u-ac.jp
Fax: +81-19-621-6355
Tel: +81-19-621-6355

c Equipe Architectures Moléculaires et Matériaux Nanostructurés, UMR CNRS 5253, Institut Charles Gerhardt, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l’Ecole Normale, 34293 Montpellier Cedex 05, France
E-mail: francoise.spirau@enscm.fr
Fax: +33 4 67 14 72 12
Tel: +33 4 67 14 72 22

Abstract

Two thiophene–phenylene semiconductors, bis(2-phenylethynyl) end-substituted oligothiophenes (diPhAc-nTs, n = 2, 3), were synthesized and studied with respect to their optical, electrochemical, structural and electrical properties. The optical and electrochemical properties of the oligomers in solution were investigated by UV-vis absorption and photoluminescence spectroscopies, and cyclic voltammetry. High vacuum evaporated thin films were investigated by optical absorption, X-ray diffraction and AFM, and implemented as p-type semiconducting layers into organic thin-film transistors (OTFTs). A comparative study in solution and in the solid state with distyryl-oligothiophenes (DSnTs, n = 2, 3) reveals the great influence of acetylenic (–C[triple bond, length as m-dash]C–) vs. olefinic (–C[double bond, length as m-dash]C–) spacers in thiophene–phenylene derivatives on electronic structure, physical properties, and device efficiencies. Substituting olefinic for acetylenic π-spacers in terthiophene-based conjugated semiconductors leads to one of incontrovertible attributes of OTFTs for low cost applications, a high mobility at low substrate temperature (Tsub) i.e. typically 25 °C. Fine-tuning in the HOMO/LUMO levels by reducing the HOMO level introduces increased air-oxidation strength of thin films where OTFTs provide exactly the same hole mobility value after 100 days in air. All the results suggested that introduction of carbon–carbon triple bonds provided an efficient route to highly air-stable organic thin film transistors.

Graphical abstract: Acetylenic spacers in phenylene end-substituted oligothiophene core for highly air-stable organic field-effect transistors

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Article information

DOI
https://doi.org/10.1039/B923352K
Article type
Paper
Submitted
06 Nov 2009
Accepted
02 Feb 2010
First published
24 Feb 2010

Phys. Chem. Chem. Phys., 2010,12, 3845-3851

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Acetylenic spacers in phenylene end-substituted oligothiophene core for highly air-stable organic field-effect transistors

A. K. Diallo, C. Videlot-Ackermann, P. Marsal, H. Brisset, F. Fages, A. Kumagai, N. Yoshimoto, F. Serein-Spirau and J. Lère-Porte, Phys. Chem. Chem. Phys., 2010, 12, 3845 DOI: 10.1039/B923352K

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