Assembly and Fiber Formation of a Gemini-Type Hexathienocoronene Amphiphile for Electrical Conduction

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• 作者：Long Chen ; Kunal S. Mali ; Sreenivasa R. Puniredd ; Martin Baumgarten ; Khaled Parvez ; Wojciech Pisula ; Steven De Feyter ; Klaus M眉llen
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：September 11, 2013
• 年：2013
• 卷：135
• 期：36
• 页码：13531-13537
• 全文大小：562K
• 年卷期：v.135,no.36(September 11, 2013)
• ISSN：1520-5126

文摘

We report the synthesis, characterization, and self-assembly of a new gemini-type amphiphilic hexathienocoronene (HTC_Gemini), which owes its amphiphilicity to two hydrophobic dodecyl chains on one side of the HTC core and two hydrophilic triethylene glycol (TEG) chains on the other. Bearing a 鈥渟ofter鈥?aromatic HTC core than the conventional hexa-peri-hexabenzocoronenes (HBC), and being more planar than contorted-hexabenzocoronenes (c-HBC), HTC_Gemini is demonstrated to yield various well-ordered assemblies in solution, at the liquid鈥搒olid interface, and in solid state by the use of different processing techniques. Regular fibers, helices, and tubes can be formed simply by processing from different solvents. At the liquid鈥搒olid interface, as visualized by scanning tunneling microscopy (STM), pairs of molecules adsorb very close to each other and arrange in the p2 plane group, driven by packing constraints and weak van der Waals interactions between adjacent molecules. HTC_Gemini also exhibits phase forming behavior in the bulk upon thermal treatment, resulting in a crystalline, herringbone-like columnar structure. Owning to an electron enriched aromatic core with respect to other reported coronenes, HTC_Gemini easily forms a stable radical cation, both in solution and in the bulk, upon oxidative doping with nitrosonium tetrafluoroborate (NOBF₄). Furthermore, light irradiation of the blend film of HTC_Gemini and phenyl-C₆₁-butyric acid methyl ester (PCBM) generates a prominent photocurrent which can be switched repeatedly with a large on/off ratio (6.0 脳 10⁴). The self-assembled structures obtained from HTC_Gemini at different length scales have potential applications in optoelectronic devices, solar cells, and redox sensors.