Heptacene: Synthesis and Its Hole-Transfer Property in Stable Thin Films

Takaaki Miyazaki; Motonori Watanabe; Toshinori Matsushima; Ching-Ting Chien; Chihaya Adachi; Shih-Sheng Sun; Hiroyuki Furuta; Tahsin J Chow

doi:10.1002/chem.202100936

Heptacene: Synthesis and Its Hole-Transfer Property in Stable Thin Films

Chemistry. 2021 Jul 21;27(41):10677-10684. doi: 10.1002/chem.202100936. Epub 2021 Jun 4.

Authors

Takaaki Miyazaki^{1

2}, Motonori Watanabe³, Toshinori Matsushima^{3

4

5}, Ching-Ting Chien⁶, Chihaya Adachi^{2

3

4

5}, Shih-Sheng Sun⁶, Hiroyuki Furuta², Tahsin J Chow^{6

7}

Affiliations

¹ Department of Chemistry, Faculty of Science, Fukuoka University, Fukuoka, 814-0180, Japan.
² Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan.
³ International Institute for Carbon-Neutral Energy Research, Kyushu University, Fukuoka, 819-0395, Japan.
⁴ Center for Organic Photonics and Electronics Research (OPERA), Kyushu University, Fukuoka, 8190395, Japan.
⁵ Japan Science and Technology Agency (JST), ERATO, Adachi Molecular Exciton Engineering Project, Fukuoka, 819-0395, Japan.
⁶ Institute of Chemistry, Academia Sinica, Taipei, 11529, Taiwan.
⁷ Department of Chemistry, Tunghai University, Taichung, 40704, Taiwan.

PMID: 33904186
DOI: 10.1002/chem.202100936

Abstract

Heptacene (1) has been produced via a monoketone precursor, 2, which was prepared from 1,2,4,5-tetrabromobenzene in nine steps in a total yield of 10 %. Compound 2 was converted to 1 quantitatively by heating at 202 °C. Heptacene exhibited high thermal stability in the solid state without any observable change over two months. To investigate the potential value of 1 as a material for p-type organic field-effect transistors (OFETs), top-contact OFET devices were fabricated by vacuum deposition of 1 onto a hexamethyldisilazane (HMDS)/SiO₂ /Si substrate. The best hole mobility performance was 2.2 cm² V^-1 s^-1 . This is the first report of stable heptacene being used in an effective device and examined for its charge carrier properties.

Keywords: heptacene; hydrocarbons; p-type organic field-effect transistors; synthetic methods; thermal conversion.

Abstract

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