Synthesis, Structures, and Photophysical Properties of Optically Stable 1,16-Dipheny1-3,14-diaryl-Substituted Tetrahydrobenzo[5]helicenediol Derivatives: Enantioselective Recognition toward Tryptophan Methyl Esters
文献类型：期刊论文
| 作者 | Fang, Lei1,2; Li, Meng1; Lin, Wei-Bin1,2; Shen, Yun1; Chen, Chuan-Feng1,2 |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2017-07-21 |
| 卷号 | 82期号:14页码:7402-7409 |
| 英文摘要 | Starting from commercially available 7-methoxytetralone, 1,16-diphenyl-3,14-dibromotetrahydrobenzo[5]helicenediol (Br-H[5]HOL) was conveniently prepared, which underwent efficient resolution to give the optically stable enantiomeric diols in gram scale by HPLC with semipreparative chiral columns. The absolute configurations of the diols were determined by the circular dichroism (CD) spectra and X-ray crystal structure. By Suzuki-Miyaura cross-coupling reactions, a series of enantiopure pi-extended 1,16-diphenyl-3,14-diaryltetrahydrobenzo[5]helicenediol derivatives (Ar-H[5]HOL) were further synthesized in high yields. The enantiomeric Ar-H[5]HOL exhibited almost identical absorption and emission spectra but showed mirror-image CD spectra and mirror-image circularly polarized luminescence properties. Moreover, it was also found that aryl substituents at the 3,14-positions could extend the chiral environment of the helical skeletons, which led to efficient enantioselective recognition of the enantiomers of tryptophan methyl esters. |
| 语种 | 英语 |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/39213]  |
| 专题 | 化学研究所_分子识别与功能实验室 |
| 作者单位 | 1.Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Fang, Lei,Li, Meng,Lin, Wei-Bin,et al. Synthesis, Structures, and Photophysical Properties of Optically Stable 1,16-Dipheny1-3,14-diaryl-Substituted Tetrahydrobenzo[5]helicenediol Derivatives: Enantioselective Recognition toward Tryptophan Methyl Esters[J]. JOURNAL OF ORGANIC CHEMISTRY,2017,82(14):7402-7409. |
| APA | Fang, Lei,Li, Meng,Lin, Wei-Bin,Shen, Yun,&Chen, Chuan-Feng.(2017).Synthesis, Structures, and Photophysical Properties of Optically Stable 1,16-Dipheny1-3,14-diaryl-Substituted Tetrahydrobenzo[5]helicenediol Derivatives: Enantioselective Recognition toward Tryptophan Methyl Esters.JOURNAL OF ORGANIC CHEMISTRY,82(14),7402-7409. |
| MLA | Fang, Lei,et al."Synthesis, Structures, and Photophysical Properties of Optically Stable 1,16-Dipheny1-3,14-diaryl-Substituted Tetrahydrobenzo[5]helicenediol Derivatives: Enantioselective Recognition toward Tryptophan Methyl Esters".JOURNAL OF ORGANIC CHEMISTRY 82.14(2017):7402-7409. |
入库方式： OAI收割
来源：化学研究所
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