Sodium Sulfide-Promoted Thiophene-Annulations: Powerful Tools for Elaborating Organic Semiconducting Materials
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- Masahiro Nakano
- Emergent Molecular Function Research Group, RIKEN Center for Emergent Matter Science (CEMS), 2-1, Hirosawa, Wako, Saitama 351-0198, Japan
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- Kazuo Takimiya
- Emergent Molecular Function Research Group, RIKEN Center for Emergent Matter Science (CEMS), 2-1, Hirosawa, Wako, Saitama 351-0198, Japan
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説明
We describe herein facile thiophene annulation reactions promoted by sodium sulfide hydrate (Na2S·9H2O) for the synthesis of acene(di)thiophenes that can be further utilized as organic semiconductors or building blocks for the elaboration of semiconducting oligomers and polymers. Sodium sulfide hydrate is an efficient source of sulfur for both the aromatic nucleophilic substitution (SNAr) reaction and the nucleophilic hydrogen substitution (SNH) reaction to give a range of electron-donating acene(di)thiophenes and an electron-deficient naphtho[2,3-b:6,7-b′]dithiophene diimide (NDTI), respectively. We also describe organic semiconducting materials on the basis of these acene(di)thiophenes and their use in organic devices, such as organic field-effect transistors and organic photovoltaics, and demonstrate that synthetic evolution is one of the keys to promoting the field of organic semiconducting materials.
収録刊行物
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- Chemistry of Materials
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Chemistry of Materials 29 (1), 256-264, 2016-11-03
American Chemical Society (ACS)
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詳細情報 詳細情報について
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- CRID
- 1360283691581641088
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- ISSN
- 15205002
- 08974756
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- 資料種別
- journal article
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- データソース種別
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