Tunable Heck-Mizoroki Reaction of Dibromonaphthalene Diimide with Aryl Ethylenes: Design, Synthesis, and Characterization of Coplanar NDI-Based Conjugated Molecules
文献类型：期刊论文
| 作者 | Gu, Chunling1,2; Li, Yangxiong1,2; Xiao, Lu1,2; Fu, Hongbing1,3; Wang, Dong1; Cheng, Liang1,2; Liu, Li1,2 |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2017-12-01 |
| 卷号 | 82期号:23页码:12806-12812 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/acs.joc.7b02140 |
| 英文摘要 | Rational design of coplanar NDI-based conjugated molecules was achieved by covalently connecting naphthalene diimide (NDI) units with aryl (Ar) groups through vinylene (V) linkers via Heck-Mizoroki reaction. Two series of products, diolefination products (ArVNDIVAr) and hydroxylated and mono-olefination products (HONDIVAr), can be obtained, respectively, in moderate to excellent yields (45-90%) under controlled conditions, in which catalyst and base play the key roles. Density functional theory calculation discloses the outstanding planarity of the two types of products. Large bathochromic shifts are observed in both the absorbance and photoluminescence spectra of the HONDIVAr (144 and 229 nm) and ArVNDIVAr (180 and 242 nm) pi-systems. Bathochromic shifts can be adjusted within the broad wavelength range by introducing 4'-substituents, either electron-withdrawing group (NO2) or electron-donating group (NMe2), in the phenyl group of aryl ethylenes. ArVNDIVArs show bigger bathochromic shifts than HONDIVArs. |
| 语种 | 英语 |
| WOS记录号 | WOS:000417342300086 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/45299]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Gu, Chunling; Liu, Li |
| 作者单位 | 1.Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, BNLMS, Beijing 100190, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.Capital Normal Univ, Dept Chem, Beijing Key Lab Opt Mat & Photon Devices, Beijing 100048, Peoples R China |
| 推荐引用方式 GB/T 7714 | Gu, Chunling,Li, Yangxiong,Xiao, Lu,et al. Tunable Heck-Mizoroki Reaction of Dibromonaphthalene Diimide with Aryl Ethylenes: Design, Synthesis, and Characterization of Coplanar NDI-Based Conjugated Molecules[J]. JOURNAL OF ORGANIC CHEMISTRY,2017,82(23):12806-12812. |
| APA | Gu, Chunling.,Li, Yangxiong.,Xiao, Lu.,Fu, Hongbing.,Wang, Dong.,...&Liu, Li.(2017).Tunable Heck-Mizoroki Reaction of Dibromonaphthalene Diimide with Aryl Ethylenes: Design, Synthesis, and Characterization of Coplanar NDI-Based Conjugated Molecules.JOURNAL OF ORGANIC CHEMISTRY,82(23),12806-12812. |
| MLA | Gu, Chunling,et al."Tunable Heck-Mizoroki Reaction of Dibromonaphthalene Diimide with Aryl Ethylenes: Design, Synthesis, and Characterization of Coplanar NDI-Based Conjugated Molecules".JOURNAL OF ORGANIC CHEMISTRY 82.23(2017):12806-12812. |
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来源：化学研究所
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