Synthesis of Dinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties
To investigate organic field-effect transistor (OFET) properties, a new thienoacene-type molecule, 4,14-dihexyldinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (C6-DNADT), consisting of π-conjugated nine aromatic rin...
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| Format: | Article |
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MDPI AG
2020-04-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/21/7/2447 |
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| author | Takumi Ishida Yuta Sawanaka Ryota Toyama Zhenfei Ji Hiroki Mori Yasushi Nishihara |
| author_facet | Takumi Ishida Yuta Sawanaka Ryota Toyama Zhenfei Ji Hiroki Mori Yasushi Nishihara |
| author_sort | Takumi Ishida |
| collection | DOAJ |
| description | To investigate organic field-effect transistor (OFET) properties, a new thienoacene-type molecule, 4,14-dihexyldinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (C6-DNADT), consisting of π-conjugated nine aromatic rings and two hexyl chains along the longitudinal molecular axis has been successfully synthesized by sequential reactions, including Negishi coupling, epoxidation, and cycloaromatization. The fabricated OFET using thin films of C6-DNADT exhibited p-channel FET properties with field-effect mobilities (<i>µ</i>) of up to 2.6 × 10<sup>−2</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>, which is ca. three times lower than that of the parent DNADT molecule (8.5 × 10<sup>−2</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>). Although this result implies that the installation of relatively short alkyl chains into the DNADT core is not suitable for transistor application, the origins for the FET performance obtained in this work is fully discussed, based on theoretical calculations and solid-state structure of C6-DNADT by grazing incidence wide-angle X-ray scattering (GIWAXS) and atomic force microscopy (AFM) analyses. The results obtained in this study disclose the effect of alkyl chains introduced onto the molecule on transistor characteristics. |
| first_indexed | 2024-03-10T20:45:23Z |
| format | Article |
| id | doaj.art-e0db7fe88f094a35bff8c378cda3889f |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T20:45:23Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-e0db7fe88f094a35bff8c378cda3889f2023-11-19T20:25:33ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672020-04-01217244710.3390/ijms21072447Synthesis of Dinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor PropertiesTakumi Ishida0Yuta Sawanaka1Ryota Toyama2Zhenfei Ji3Hiroki Mori4Yasushi Nishihara5Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, JapanGraduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, JapanGraduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, JapanGraduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, JapanResearch Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, JapanResearch Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, JapanTo investigate organic field-effect transistor (OFET) properties, a new thienoacene-type molecule, 4,14-dihexyldinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (C6-DNADT), consisting of π-conjugated nine aromatic rings and two hexyl chains along the longitudinal molecular axis has been successfully synthesized by sequential reactions, including Negishi coupling, epoxidation, and cycloaromatization. The fabricated OFET using thin films of C6-DNADT exhibited p-channel FET properties with field-effect mobilities (<i>µ</i>) of up to 2.6 × 10<sup>−2</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>, which is ca. three times lower than that of the parent DNADT molecule (8.5 × 10<sup>−2</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>). Although this result implies that the installation of relatively short alkyl chains into the DNADT core is not suitable for transistor application, the origins for the FET performance obtained in this work is fully discussed, based on theoretical calculations and solid-state structure of C6-DNADT by grazing incidence wide-angle X-ray scattering (GIWAXS) and atomic force microscopy (AFM) analyses. The results obtained in this study disclose the effect of alkyl chains introduced onto the molecule on transistor characteristics.https://www.mdpi.com/1422-0067/21/7/2447organic field-effect transistor (OFET)thienoacenep-type semiconductorNegishi coupling reactioncycloaromatizationfastener effect |
| spellingShingle | Takumi Ishida Yuta Sawanaka Ryota Toyama Zhenfei Ji Hiroki Mori Yasushi Nishihara Synthesis of Dinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties International Journal of Molecular Sciences organic field-effect transistor (OFET) thienoacene p-type semiconductor Negishi coupling reaction cycloaromatization fastener effect |
| title | Synthesis of Dinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties |
| title_full | Synthesis of Dinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties |
| title_fullStr | Synthesis of Dinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties |
| title_full_unstemmed | Synthesis of Dinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties |
| title_short | Synthesis of Dinaphtho[2,3-<i>d</i>:2’,3’-<i>d</i>’]anthra[1,2-<i>b</i>:5,6-<i>b</i>’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties |
| title_sort | synthesis of dinaphtho 2 3 i d i 2 3 i d i anthra 1 2 i b i 5 6 i b i dithiophene dnadt derivatives effect of alkyl chains on transistor properties |
| topic | organic field-effect transistor (OFET) thienoacene p-type semiconductor Negishi coupling reaction cycloaromatization fastener effect |
| url | https://www.mdpi.com/1422-0067/21/7/2447 |
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