Novel Diketopyrrolopyrrole-Based π-Conjugated Molecules Synthesized Via One-Pot Direct Arylation Reaction
Diketopyrrolopyrrole (DPP) is an important type of π-conjugated building block for high-performance organic electronic materials. DPP-based conjugated materials are usually synthesized via Suzuki, Stille, or Negishi cross-coupling reactions, which require organometallic precursors. In this...
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| Format: | Article |
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MDPI AG
2019-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/9/1760 |
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| author | Hui Liu Xiao-Feng Zhang Jing-Zhao Cheng Ai-Guo Zhong He-Rui Wen Shi-Yong Liu |
| author_facet | Hui Liu Xiao-Feng Zhang Jing-Zhao Cheng Ai-Guo Zhong He-Rui Wen Shi-Yong Liu |
| author_sort | Hui Liu |
| collection | DOAJ |
| description | Diketopyrrolopyrrole (DPP) is an important type of π-conjugated building block for high-performance organic electronic materials. DPP-based conjugated materials are usually synthesized via Suzuki, Stille, or Negishi cross-coupling reactions, which require organometallic precursors. In this paper, a series of novel phenyl-cored DPP molecules, including five <i>meta</i>-phenyl-cored molecules and four <i>para</i>-phenyl-cored molecules, have been synthesized in moderate to good yields, in a facile manner, through the Pd-catalyzed direct arylation of C−H bonds, and their optoelectrical properties have been investigated in detail. All new molecules have been fully characterized by NMR, MALDI-TOF MS, elemental analysis, UV−visible spectroscopy, and cyclic voltammetry. This synthetic strategy has evident advantages of atom- and step-economy and low cost, compared with traditional cross-coupling reactions. |
| first_indexed | 2024-12-23T13:08:08Z |
| format | Article |
| id | doaj.art-d5fa45d33aa240fc8bd2043a6b57cf6c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-23T13:08:08Z |
| publishDate | 2019-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d5fa45d33aa240fc8bd2043a6b57cf6c2022-12-21T17:45:50ZengMDPI AGMolecules1420-30492019-05-01249176010.3390/molecules24091760molecules24091760Novel Diketopyrrolopyrrole-Based π-Conjugated Molecules Synthesized Via One-Pot Direct Arylation ReactionHui Liu0Xiao-Feng Zhang1Jing-Zhao Cheng2Ai-Guo Zhong3He-Rui Wen4Shi-Yong Liu5School of Metallurgical and Chemical Engineering, Jiangxi University of Science and Technology, Ganzhou 341000, ChinaSchool of Metallurgical and Chemical Engineering, Jiangxi University of Science and Technology, Ganzhou 341000, ChinaSchool of Metallurgical and Chemical Engineering, Jiangxi University of Science and Technology, Ganzhou 341000, ChinaDepartment of Chemistry, Taizhou University, Taizhou 317000, ChinaSchool of Metallurgical and Chemical Engineering, Jiangxi University of Science and Technology, Ganzhou 341000, ChinaSchool of Metallurgical and Chemical Engineering, Jiangxi University of Science and Technology, Ganzhou 341000, ChinaDiketopyrrolopyrrole (DPP) is an important type of π-conjugated building block for high-performance organic electronic materials. DPP-based conjugated materials are usually synthesized via Suzuki, Stille, or Negishi cross-coupling reactions, which require organometallic precursors. In this paper, a series of novel phenyl-cored DPP molecules, including five <i>meta</i>-phenyl-cored molecules and four <i>para</i>-phenyl-cored molecules, have been synthesized in moderate to good yields, in a facile manner, through the Pd-catalyzed direct arylation of C−H bonds, and their optoelectrical properties have been investigated in detail. All new molecules have been fully characterized by NMR, MALDI-TOF MS, elemental analysis, UV−visible spectroscopy, and cyclic voltammetry. This synthetic strategy has evident advantages of atom- and step-economy and low cost, compared with traditional cross-coupling reactions.https://www.mdpi.com/1420-3049/24/9/1760diketopyrrolopyrrole (DPP)direct arylationπ-conjugated moleculescyclic voltammetryatom economy |
| spellingShingle | Hui Liu Xiao-Feng Zhang Jing-Zhao Cheng Ai-Guo Zhong He-Rui Wen Shi-Yong Liu Novel Diketopyrrolopyrrole-Based π-Conjugated Molecules Synthesized Via One-Pot Direct Arylation Reaction Molecules diketopyrrolopyrrole (DPP) direct arylation π-conjugated molecules cyclic voltammetry atom economy |
| title | Novel Diketopyrrolopyrrole-Based π-Conjugated Molecules Synthesized Via One-Pot Direct Arylation Reaction |
| title_full | Novel Diketopyrrolopyrrole-Based π-Conjugated Molecules Synthesized Via One-Pot Direct Arylation Reaction |
| title_fullStr | Novel Diketopyrrolopyrrole-Based π-Conjugated Molecules Synthesized Via One-Pot Direct Arylation Reaction |
| title_full_unstemmed | Novel Diketopyrrolopyrrole-Based π-Conjugated Molecules Synthesized Via One-Pot Direct Arylation Reaction |
| title_short | Novel Diketopyrrolopyrrole-Based π-Conjugated Molecules Synthesized Via One-Pot Direct Arylation Reaction |
| title_sort | novel diketopyrrolopyrrole based π conjugated molecules synthesized via one pot direct arylation reaction |
| topic | diketopyrrolopyrrole (DPP) direct arylation π-conjugated molecules cyclic voltammetry atom economy |
| url | https://www.mdpi.com/1420-3049/24/9/1760 |
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