Design and synthesis of proton-dopable organic semiconductors

This paper shows how protonated 3,4-ethylene dioxythiophene moieties can be used as an end group to make organic conductors. An organic semiconductor 2,5-bis(5-(2,3-dihydrothieno[3,4- b ][1,4]dioxin-5-yl)-3-dodecylthiophen-2-yl)thieno[3,2- b ]thiophene is designed and synthesized. This molecule coul...

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Bibliographic Details
Published in:RSC advances 2022-02, Vol.12 (11), p.6748-6754
Main Authors: Yin, Chenzhu, Mukaida, Masakazu, Horike, Shohei, Kirihara, Kazuhiro, Yamane, Shogo, Zhang, Zhenya, Wei, Qingshuo
Format: Article
Language:English
Subjects:
Absorption
Adducts
Chemical synthesis
Chemistry
Conductors
Dioxins
Electrical resistivity
Near infrared radiation
NMR
Nuclear magnetic resonance
Organic semiconductors
Protons
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Summary:This paper shows how protonated 3,4-ethylene dioxythiophene moieties can be used as an end group to make organic conductors. An organic semiconductor 2,5-bis(5-(2,3-dihydrothieno[3,4- b ][1,4]dioxin-5-yl)-3-dodecylthiophen-2-yl)thieno[3,2- b ]thiophene is designed and synthesized. This molecule could be doped by protonic acid in both solution and solid-state, resulting in a broad absorption in the near-infrared range corresponding to polaron and bipolaron absorption. Electrical conductivity of ca. 0.1 S cm −1 was obtained at 100 °C (to avoid the water uptake by the acid). The adducts with protons bound at the end-thiophene α-position were confirmed by 1 H Nuclear Magnetic Resonance spectra. The use of protonated 3,4-ethylenedioxythiophene moieties as an end group could be a promising approach to prepare organic conductors.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra00216g