A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor Units
A-π-D-π-A-based small molecules 6,6′-((thiophene-2,5-diylbis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) <b>(TDPP-T)</b> and 6,6′-(((2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis(ethyne-2,1-diyl))bis...
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MDPI AG
2021-07-01
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| Series: | Micromachines |
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| Online Access: | https://www.mdpi.com/2072-666X/12/7/817 |
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| author | Baji Shaik Mujeeb Khan Mohammed Rafi Shaik Mohammed A.F. Sharaf Doumbia Sekou Sang-Gyeong Lee |
| author_facet | Baji Shaik Mujeeb Khan Mohammed Rafi Shaik Mohammed A.F. Sharaf Doumbia Sekou Sang-Gyeong Lee |
| author_sort | Baji Shaik |
| collection | DOAJ |
| description | A-π-D-π-A-based small molecules 6,6′-((thiophene-2,5-diylbis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) <b>(TDPP-T)</b> and 6,6′-(((2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) <b>(TDPP-EDOT)</b> have been designed and synthesized. The diketopyrrolopyrrole acts as an electron acceptor, while the thiophene or 3,4-ethylenedioxythiophene acts as an electron donor. The donor–acceptor groups are connected by an ethynyl bridge to further enhance the conjugation. The optoelectronics, electrochemical, and thermal properties have been investigated. Organic thin film transistor (OTFT) devices prepared from <b>TDPP-T</b> and <b>TDPP-EDOT</b> have shown p-type mobility. In as cast films, <b>TDPP-T</b> and <b>TDPP-EDOT</b> have shown a hole mobility of 5.44 × 10<sup>−6</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup> and 4.13 × 10<sup>−6</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>, respectively. The increase in the mobility of <b>TDPP-T</b> and <b>TDPP-EDOT</b> OTFT devices was observed after annealing at 150 °C, after which the mobilities were 3.11 × 10<sup>−4</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup> and 2.63 × 10<sup>−4</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>, respectively. |
| first_indexed | 2024-03-10T09:31:07Z |
| format | Article |
| id | doaj.art-0e102b234c684184a59b3c60d32f50ff |
| institution | Directory Open Access Journal |
| issn | 2072-666X |
| language | English |
| last_indexed | 2024-03-10T09:31:07Z |
| publishDate | 2021-07-01 |
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| series | Micromachines |
| spelling | doaj.art-0e102b234c684184a59b3c60d32f50ff2023-11-22T04:25:00ZengMDPI AGMicromachines2072-666X2021-07-0112781710.3390/mi12070817A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor UnitsBaji Shaik0Mujeeb Khan1Mohammed Rafi Shaik2Mohammed A.F. Sharaf3Doumbia Sekou4Sang-Gyeong Lee5Department of Chemistry, Research Institute of Natural Science (RINS), Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University, Jinju 660-701, South KoreaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Industrial Engineering, College of Engineering, King Saud University, P.O. Box 800, Riyadh 11421, Saudi ArabiaDepartment of Agricultural Extension and Rural Society, College of Food and Agriculture Sciences, King Saud University, P.O. Box 2460, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Research Institute of Natural Science (RINS), Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University, Jinju 660-701, South KoreaA-π-D-π-A-based small molecules 6,6′-((thiophene-2,5-diylbis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) <b>(TDPP-T)</b> and 6,6′-(((2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) <b>(TDPP-EDOT)</b> have been designed and synthesized. The diketopyrrolopyrrole acts as an electron acceptor, while the thiophene or 3,4-ethylenedioxythiophene acts as an electron donor. The donor–acceptor groups are connected by an ethynyl bridge to further enhance the conjugation. The optoelectronics, electrochemical, and thermal properties have been investigated. Organic thin film transistor (OTFT) devices prepared from <b>TDPP-T</b> and <b>TDPP-EDOT</b> have shown p-type mobility. In as cast films, <b>TDPP-T</b> and <b>TDPP-EDOT</b> have shown a hole mobility of 5.44 × 10<sup>−6</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup> and 4.13 × 10<sup>−6</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>, respectively. The increase in the mobility of <b>TDPP-T</b> and <b>TDPP-EDOT</b> OTFT devices was observed after annealing at 150 °C, after which the mobilities were 3.11 × 10<sup>−4</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup> and 2.63 × 10<sup>−4</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>, respectively.https://www.mdpi.com/2072-666X/12/7/817organic thin film transistorshole mobilitysmall moleculesdonor-acceptordiketopyrrolopyrrole |
| spellingShingle | Baji Shaik Mujeeb Khan Mohammed Rafi Shaik Mohammed A.F. Sharaf Doumbia Sekou Sang-Gyeong Lee A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor Units Micromachines organic thin film transistors hole mobility small molecules donor-acceptor diketopyrrolopyrrole |
| title | A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor Units |
| title_full | A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor Units |
| title_fullStr | A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor Units |
| title_full_unstemmed | A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor Units |
| title_short | A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor Units |
| title_sort | a π d π a based small molecules for otfts containing diketopyrrolopyrrole as acceptor units |
| topic | organic thin film transistors hole mobility small molecules donor-acceptor diketopyrrolopyrrole |
| url | https://www.mdpi.com/2072-666X/12/7/817 |
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