A Directly Linked Ferrocene–Naphthalenediimide Conjugate: Precise Control of Stacking Structures of π-Systems by Redox Stimuli


  • We are grateful to Prof. Dr. H. Oshio and Dr. J. Kuwabara for their helpful discussion. We also appreciate Dr. Y. Kobayashi for her support of UV/Vis/NIR spectroscopy in solid states. This research was supported by Grants-in-Aid for Scientific Research for Priority Area “Coordination Programming” (area 2107) to M.T., “Nanotechnology Platform Project”, and Center of Materials Research for Low Carbon Emission from MEXT (Japan). A.T. appreciates support from a JSPS fellowship for young scientists.


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A ferrocene derivative having directly connected naphthalenediimide moieties has been synthesized. The stacking–destacking structures of the naphthalenediimides can be switched in response to redox stimuli by associating with the pivoting motion of ferrocene. The conformation and the electronic structure of naphthalenediimides are elucidated quantitatively in each electron-transfer state. The composite exhibited n-type semiconducting behavior.