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Orthogonally Functionalized Naphthodithiophenes: Selective Protection and Borylation
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- Shoji Shinamura
- Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
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- Ryusuke Sugimoto
- Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
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- Naoyuki Yanai
- Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
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- Noriko Takemura
- Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
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- Tomoya Kashiki
- Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
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- Itaru Osaka
- Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
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- Eigo Miyazaki
- Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
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- Kazuo Takimiya
- Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
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Description
Selective functionalization protocols of naphtho[1,2-b;5,6-b']dithiophene (NDT3) by combining protection of the thiophene α-positions and direct borylation on the naphthalene core are described, which allows synthesizing a number of new NDT3-based building blocks with various substituents and isomeric NDT3-based polymers with different main chain structures. The same protocol is applicable to other isomeric naphthodithiophenes (NDTs), which affords a set of key building blocks for the development of elaborated functional π-materials.
Journal
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- Organic Letters
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Organic Letters 14 (18), 4718-4721, 2012-09-12
American Chemical Society (ACS)
