A general method for constructing optically active supramolecular assemblies from intrinsically achiral water-insoluble free-base porphyrins
文献类型：期刊论文
| 作者 | Zhang, Yiqun; Chen, Penglei ; Liu, Minghua
|
| 刊名 | CHEMISTRY-A EUROPEAN JOURNAL
 |
| 出版日期 | 2008 |
| 卷号 | 14期号:6页码:1793-1803 |
| 关键词 | Porphyrinoids Supramolecular Assemblies Symmetry Breaking Thin Films |
| ISSN号 | 0947-6539 |
| DOI | 10.1002/chem.200701333 |
| 英文摘要 | We have developed a general method to construct optically active porphyrin supramolecular assemblies by using a simple air-water interfacial assembly process. The method involved the in situ diprotonation of the free-base porphyrins at the air-water interface and subsequent assembly under compression. We showed that two intrinsically achiral water-insoluble free-base porphyrin derivatives, 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphine (H2OEP) and 5,10,15,20-tetra-p-tolyl-21 H,23H-porphine (H2TPPMe), could be diprotonated when spread onto a 2.4 M hydrochloric acid solution surface, and the Langmuir-Schaefer (LS) films fabricated from the subphase exhibited strong circular dichroism (CD) absorption, whereas those fabricated from pure Milli-Q water subphase did not. The experimental data suggested that the helical stacking of the achiral porphyrin building blocks was responsible for the supramolecular chirality of the assemblies. Interestingly, such a method was successfully applied to a series of other intrinsically achiral free-base porphyrins such as 5,10,15,20-tetrakis(4-methoxyphenyl)-21 H,23H-porphine (H2TPPOMe), 5,10,15,20-tetraphenyl-21H,23H-porphine (H2TPP), 5,10,15,20-tetrakis(4-(allyloxy)phenyl)-21H,23H-porphine (H(2)TPPOA), and 5,10,1.5,20-tetrakis(3,5-dimethoxyphenyl)-21H,23H-porphine (H2TPPDOMe). A possible mechanism has been proposed. The method provides a facile way to obtain optically active porphyrin supramolecular assemblies by using intrinsically achiral water-insoluble free-base porphyrin derivatives. |
| 语种 | 英语 |
| WOS记录号 | WOS:000253470900012 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/65263]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Chen, Penglei |
| 作者单位 | Chinese Acad Sci, Inst Chem, CAS Key Lab Colloid Interface & Chem Thermodynam, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhang, Yiqun,Chen, Penglei,Liu, Minghua. A general method for constructing optically active supramolecular assemblies from intrinsically achiral water-insoluble free-base porphyrins[J]. CHEMISTRY-A EUROPEAN JOURNAL,2008,14(6):1793-1803. |
| APA | Zhang, Yiqun,Chen, Penglei,&Liu, Minghua.(2008).A general method for constructing optically active supramolecular assemblies from intrinsically achiral water-insoluble free-base porphyrins.CHEMISTRY-A EUROPEAN JOURNAL,14(6),1793-1803. |
| MLA | Zhang, Yiqun,et al."A general method for constructing optically active supramolecular assemblies from intrinsically achiral water-insoluble free-base porphyrins".CHEMISTRY-A EUROPEAN JOURNAL 14.6(2008):1793-1803. |
入库方式： OAI收割
来源：化学研究所
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