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Article dans une revue

Quaterthiophenes with Terminal Indeno[1,2-b]thiophene Units as p-Type Organic Semiconductors

Abstract :

Quaterthiophenes 4T, Oct-4T, and Tol-4T based on a central 2,2′-bithiophene core α,ω-terminated with 4,4-unsubstituted and 4,4-disubstituted n-octyl or p-tolyl indeno[1,2-b]thiophene have been synthesized by Stille or Miyaura−Suzuki couplings. Compound 4T was also synthesized by an alternative route involving a soluble precursor bearing solubilizing trimethylsilyl groups which have been eliminated in the last step. The electronic properties of the compounds have been analyzed by cyclic voltammetry, UV−vis absorption and fluorescence emission spectroscopy. Thermal evaporation of 4T and Oct-4T leads to crystalline thin films and UV−vis absorption and X-ray diffraction data for these films suggest that the molecules adopt a quasi-vertical orientation onto the substrate. Strong π-π intermolecular interactions have been observed for 4T but not for molecules Oct-4T due to the presence of n-octyl chains. Sublimed thin films of Tol-4T show an amorphous character. The characterization of field-effect transistors fabricated from these three materials gave a hole-mobility of 2.2 × 10−2 cm2 V−1 s−1 with an on/off ratio of 2.2 × 104 for 4T while no field-effect was observed for Oct-4T and Tol-4T.

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https://hal.univ-angers.fr/hal-03343391
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Soumis le : mardi 14 septembre 2021 - 10:33:17
Dernière modification le : jeudi 9 décembre 2021 - 15:46:05
Archivage à long terme le : : mercredi 15 décembre 2021 - 18:16:06

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2009_-_j._org._chem.pdf
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Laurent Pouchain, Olivier Alévêque, Yohann Nicolas, Agathe Oger, Charles-Henri Le Régent, et al.. Quaterthiophenes with Terminal Indeno[1,2-b]thiophene Units as p-Type Organic Semiconductors. Journal of Organic Chemistry, American Chemical Society, 2009, 74 (3), pp.1054 - 1064. ⟨10.1021/jo802028n⟩. ⟨hal-03343391⟩

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