Long-Range Order in Supramolecular πassemblies in Discrete Multidecker Naphthalenediimides

Sudhir Kumar Keshri, Tomoya Ishizuka, Takahiko Kojima, Yoshitaka Matsushita, Masayuki Takeuchi

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


We report herein the solution and solid-state studies of conformationally flexible multidecker naphthalenediimides (NDIs) in which the chromophoric NDI units intramolecularly assemble into a series of discrete π-stacks. The X-ray crystallography reveals the existence of exclusively all-syn NDIs orientations in lower congeners while all-anti in a higher congener, suggesting short- to long-range π···πinteractions throughout the slipped πNDI chromophoric array. The UV/vis and fluorescence spectra evaluate the discrete π-stacks by remarkable optical changes upon cooling in solution. Furthermore, we carried out a systematic electrochemical investigation to gain an insight into redox properties of the long-range π-stacked structures. The higher congener (5NDI) shows a ten-electron reversible reduction process in a small working potential window (∼0.8 V). To our knowledge, this is an unusual observation in an organic molecular system to undergo up to ten-electron reduction. These results pave the way to design multidecker π-stacks in which structural control with specific electronic properties would be engineered.

Original languageEnglish
Pages (from-to)3238-3244
Number of pages7
JournalJournal of the American Chemical Society
Issue number8
Publication statusPublished - 2021 Mar 3


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