Synthesis, Morphology, and Field-Effect Mobility of Anthradithiophenes

The synthesis, thin-film morphology, and hole mobility in thin-film transistors (TFTs) of compounds based on the novel anthradithiophene (ADT) ring system are reported. The parent compound and its 2,8-dihexyl, didodecyl, and dioctadecyl derivatives (DHADT, DDADT, and DOADT, respectively), synthesize...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1998-02, Vol.120 (4), p.664-672
Main Authors: Laquindanum, Joyce G, Katz, Howard E, Lovinger, Andrew J
Format: Article
Language:English
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Summary:The synthesis, thin-film morphology, and hole mobility in thin-film transistors (TFTs) of compounds based on the novel anthradithiophene (ADT) ring system are reported. The parent compound and its 2,8-dihexyl, didodecyl, and dioctadecyl derivatives (DHADT, DDADT, and DOADT, respectively), synthesized via alkylated thiophene dicarboxaldehyde acetals, were investigated. They all form highly ordered polycrystalline vacuum-evaporated films with mobilities as high as 0.15 cm2/(V s), as high as has ever been observed for a polycrystalline organic material. DOADT has a mobility of 0.06 cm2/(V s) even though 70% of its molecular volume is occupied by hydrocarbon chains. DHADT was cast from solution under atmospheric conditions onto a TFT giving a mobility of 0.01−0.02 cm2/(V s). Thus, the alkylated ADTs combine a pentacene-like intrinsic mobility with greater solubility and oxidative stability.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9728381