Ferrocene-Alkynyl Conjugated Molecular Wires: Synthesis, Characterization, and Conductance Properties
| Autor: | Yaofeng Yuan, Ye Yuan, Da-Qiang Lin, Bing-Wei Mao, Jian-Feng Yan |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry Stacking Sonogashira coupling General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences law.invention Molecular wire chemistry.chemical_compound Delocalized electron Crystallography Ferrocene law Moiety Scanning tunneling microscope Break junction |
| Zdroj: | Chemistry - A European Journal. 24:3545-3555 |
| ISSN: | 0947-6539 |
| DOI: | 10.1002/chem.201705176 |
| Popis: | A novel series of 1,2,3-substituted ferrocene-based wires a1-a2 and b4-b5 have been synthesized by using an iterative Pd-mediated Sonogashira cross-coupling methodology. The molecular structures of a2 and b3 were determined by single-crystal X-ray analysis. Electrochemical data showed that there was a strong electronic communication among the ferrocenyl moieties in b1-b5. The UV absorption spectra indicated that replacing the 1,1'-substituted ferrocene unit with a 1,2,3-substituted ferrocene moiety causes delocalization of electrons in the extended π orbitals. The self-assembled monolayers of wire a1 and a2 on Au surfaces have been comprehensively characterized by electrochemistry and scanning tunneling microscopy break junction. The data demonstrated that 1,2,3-substituted ferrocene-based wires reduced the intermolecular π-π stacking, and furthermore solved the rotation problem in the 1,1'-substituted ferrocene-based wires. |
| Databáze: | OpenAIRE |
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