Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 14, Pages 3545-3555Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201705176
Keywords
1,2,3-substituted ferrocene; electrochemistry; molecular junctions; molecular wires; scanning tunneling microscopy break junction (STM-BJ)
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Funding
- National Natural Science Foundation of China [21642009, 21372043, 21772023]
- State Key Laboratory of Physical Chemistry of Solid Surfaces
- College of Chemistry and Chemical Engineering Open Topic [201406]
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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 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 - stacking, and furthermore solved the rotation problem in the 1,1-substituted ferrocene-based wires.
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