| Synthesis, spectroscopic, electrochemical and pb2+-binding studies of tetrathiafulvalene acetylene derivatives | |
| Zhao, Yao-Peng; Wu, Li-Zhu; Si, Gang; Liu, Yan; Xue, Hai; Zhang, Li-Ping; Tung, Chen-Ho | |
| 刊名 | Journal of organic chemistry
 |
| 2007-05-11 | |
| 卷号 | 72期号:10页码:3632-3639 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/jo0622577 |
| 通讯作者 | Wu, li-zhu(lzwu@mail.ipc.ac.cn) |
| 英文摘要 | A series of tetrathiafulvalene acetylene derivatives, [ttf-cc-a] [a = c6h4n(ch3)(2)-4 (1), c6h4och3-4 (2), c6h5 (3), c6h4f-4 (4), c6h4no2-4 (5), c5h4n-2 (6), c5h4n-3 (7), and c5h4n-4 (8)], have been designed and synthesized to provide insight into the nature of the donor-acceptor interaction via a pi-conjugated triple bond. the x-ray crystal structure of [ttf-(cc)-c6h4och3-4] (2) reveals that the phenyl ring linked by acetylene is almost coplanar to the plane of ttf with a dihedral angle of 3.6 degrees. the strong intermolecular c-h center dot center dot center dot o hydrogen bonding was found to direct the molecular helical assemblies with a screw pitch of 5.148 angstrom when viewed along the a-axis. spectroscopic and electrochemical behaviors of the tetrathiafulvalene acetylene derivatives demonstrate that the ttf unit interacts with the electron-accepting group through the triple bond, thus leading to the intramolecular charge transfer. the pyridine-substituted ttf compounds 6-8 show remarkable sensing and coordinating properties toward pb2+. comparison of the spectroscopic and electrochemical properties and the calculation at the b3lyp/6-31g* level available in gaussian 03 reveals that varying the bridged unit of the ttf-pi-a system from a double bond to a triple bond leads to positive shifts for the first and second oxidation potentials of the ttf moieties, while the extent of intramolecular charge transfer interactions through the pi-conjugated triple bond is smaller than that through the double bond. |
| WOS关键词 | INTRAMOLECULAR CHARGE-TRANSFER ; NONLINEAR-OPTICAL PROPERTIES ; RANGE ELECTRON-TRANSFER ; MOLECULAR WIRES ; SUPRAMOLECULAR CHEMISTRY ; DIMERIC TETRATHIAFULVALENES ; BUILDING-BLOCKS ; RADICAL-CATION ; NLO PROPERTIES ; PUSH-PULL |
| WOS研究方向 | Chemistry |
| WOS类目 | Chemistry, Organic |
| 语种 | 英语 |
| 出版者 | AMER CHEMICAL SOC |
| WOS记录号 | WOS:000246206700004 |
| 内容类型 | 期刊论文 |
| URI标识 | http://www.corc.org.cn/handle/1471x/2382551 |
| 专题 | 中国科学院大学 |
| 通讯作者 | Wu, Li-Zhu |
| 作者单位 | 1.Tech Inst Phys & Chem, Lab Organ Optoelect Funct Mat & Mol Engn, Beijing 100080, Peoples R China 2.Grad Univ, Chinese Acad Sci, Beijing 100080, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhao, Yao-Peng,Wu, Li-Zhu,Si, Gang,et al. Synthesis, spectroscopic, electrochemical and pb2+-binding studies of tetrathiafulvalene acetylene derivatives[J]. Journal of organic chemistry,2007,72(10):3632-3639. |
| APA | Zhao, Yao-Peng.,Wu, Li-Zhu.,Si, Gang.,Liu, Yan.,Xue, Hai.,...&Tung, Chen-Ho.(2007).Synthesis, spectroscopic, electrochemical and pb2+-binding studies of tetrathiafulvalene acetylene derivatives.Journal of organic chemistry,72(10),3632-3639. |
| MLA | Zhao, Yao-Peng,et al."Synthesis, spectroscopic, electrochemical and pb2+-binding studies of tetrathiafulvalene acetylene derivatives".Journal of organic chemistry 72.10(2007):3632-3639. |
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