Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation
文献类型：期刊论文
| 作者 | Qiu, Li1,3; Wang, Xiao1 ; Zhao, Na1,3; Xu, Shiliang1,2; An, Zengjian1; Zhuang, Xuhui1,3; Lan, Zhenggang1; Wen, Lirong2; Wan, Xiaobo1
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| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
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| 出版日期 | 2014-12-05 |
| 卷号 | 79期号:23页码:11339-11348 |
| 英文摘要 | A newly developed reductive ring closure methodology to heteroacenes bearing a dihydropyrrolo[3,2-b]pyrrole core was systematically studied for its scope and limitation. The methodology involves (i) the cyclization of an o-aminobenzoic acid ester derivative to give an eight-membered cyclic dilactam, and (ii) the conversion of the dilactams into the corresponding diimidoyl chloride, which undergoes (iii) reductive ring closure to install the dihydropyrrolo[3,2-b]pyrrole core. The first step of the methodology plays the key role due to its substrate limitation, which suffers from the competition of oligomerization and hydrolysis. All the dilactams could successfully convert to the corresponding diimidoyl chlorides, most of which succeeded to give the dihydropyrrolo[3,2-b]pyrrole core. The influence of the substituents and the elongation of conjugated length on the photophysical properties of the obtained heteroacenes were then investigated systematically using UV-vis spectroscopy and cyclic voltammetry. It was found that chlorination and fluorination had quite a different effect on the photophysical properties of the heteroacene, and the ring fusing pattern also had a drastic influence on the band gap of the heteroacene. The successful preparation of a series of heteroacenes bearing a dihydropyrrolo[3,2-b]pyrrole core would provide a wide variety of candidates for further fabrication of organic field-effect transistor devices. |
| WOS标题词 | Science & Technology ; Physical Sciences |
| 类目[WOS] | Chemistry, Organic |
| 研究领域[WOS] | Chemistry |
| 关键词[WOS] | FIELD-EFFECT TRANSISTORS ; ORGANIC SEMICONDUCTORS ; OPTICAL-PROPERTIES ; HIGH-PERFORMANCE ; DERIVATIVES ; INDOLE ; BASE |
| 收录类别 | SCI ; IC |
| 语种 | 英语 |
| WOS记录号 | WOS:000346038300005 |
| 公开日期 | 2015-12-24 |
| 源URL | [http://ir.qibebt.ac.cn/handle/337004/6279]  |
| 专题 | 青岛生物能源与过程研究所_生物基及仿生高分子材料团队 |
| 作者单位 | 1.Chinese Acad Sci, CAS Key Lab Biobased Mat, Qingdao Inst Bioenergy & Bioproc Technol, Qingdao 266101, Peoples R China 2.Qingdao Univ Sci & Technol, State Key Lab Base Ecochem Engn, Coll Chem & Mol Engn, Qingdao 266042, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Qiu, Li,Wang, Xiao,Zhao, Na,et al. Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(23):11339-11348. |
| APA | Qiu, Li.,Wang, Xiao.,Zhao, Na.,Xu, Shiliang.,An, Zengjian.,...&Wan, Xiaobo.(2014).Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation.JOURNAL OF ORGANIC CHEMISTRY,79(23),11339-11348. |
| MLA | Qiu, Li,et al."Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation".JOURNAL OF ORGANIC CHEMISTRY 79.23(2014):11339-11348. |
入库方式： OAI收割
来源：青岛生物能源与过程研究所
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