Electron-deficient N-heteroaromatic linkers for the elaboration of large, soluble polycyclic aromatic hydrocarbons and their use in the synthesis of some very large transition metal complexes
文献类型：期刊论文
| 作者 | Fogel, Yulia; Kastler, Marcel; Wang, Zhaohui; Andrienko, Denis; Bodwell, Graham J.; Muellen, Klaus |
| 刊名 | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
 |
| 出版日期 | 2007-09-26 |
| 卷号 | 129期号:38页码:11743-11749 |
| ISSN号 | 0002-7863 |
| DOI | 10.1021/ja072521t |
| 英文摘要 | The selective oxidation of the perimeter of an extended polycyclic aromatic hydrocarbon (PAH), namely a six-fold tert-butylated tetrabenzo[bc,ef,hi,uv]ovalene, led to the formation of an alpha-cliketone. The newly installed carbonyl centers allowed this building block to be converted into the largest known heteroatom-containing PAHs (up to 224 atoms in the aromatic core) by way of the quinoxaline ring condensation reaction. The tert-butyl substituents caused a distortion of the usually planar aromatic frameworks, which hampered the aggregation tendency of the extended aromatic pi-systems and led to extraordinarily high solubilities. All of the systems described here, even the giant phthalocyanine, could thus be purified using standard chromatographic techniques and characterized using typical spectroscopic methods. For the first time, fully resolved H-1 NMR spectra of soluble, diamagnetic, 98- and 104-atomcontaining aromatic systems are presented. The computed and experimental UV/vis spectra emphasize the dependence of the characteristic alpha-, p-, and beta-bands upon the size of the PAHs. It was also possible to obtain the largest known ligand to yet be complexed around a ruthenium center. A quadrupolar solvatochromic effect was observed when two donating PAH moieties were fused to an accepting quinoxaline center, in which case the photoluminescence spanned a range of about 80 nm. Electrochemical properties of the new nanographenes were investigated using cyclic voltammetry, and this showed quasi-reversible reductions. |
| 语种 | 英语 |
| WOS记录号 | WOS:000249693800023 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/60975]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Muellen, Klaus |
| 作者单位 | 1.Max Planck Inst Polymer Res, D-55128 Mainz, Germany 2.Chinese Acad Sci, Inst Chem, Beijing Natl Lab Molm Sci, Key Lab Organ Solids, Beijing 100080, Peoples R China 3.Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada |
| 推荐引用方式 GB/T 7714 | Fogel, Yulia,Kastler, Marcel,Wang, Zhaohui,et al. Electron-deficient N-heteroaromatic linkers for the elaboration of large, soluble polycyclic aromatic hydrocarbons and their use in the synthesis of some very large transition metal complexes[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2007,129(38):11743-11749. |
| APA | Fogel, Yulia,Kastler, Marcel,Wang, Zhaohui,Andrienko, Denis,Bodwell, Graham J.,&Muellen, Klaus.(2007).Electron-deficient N-heteroaromatic linkers for the elaboration of large, soluble polycyclic aromatic hydrocarbons and their use in the synthesis of some very large transition metal complexes.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,129(38),11743-11749. |
| MLA | Fogel, Yulia,et al."Electron-deficient N-heteroaromatic linkers for the elaboration of large, soluble polycyclic aromatic hydrocarbons and their use in the synthesis of some very large transition metal complexes".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 129.38(2007):11743-11749. |
入库方式： OAI收割
来源：化学研究所
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