Discrete π Stack of a Tweezer-Shaped Naphthalenediimide–Anthracene Conjugate

Sudhir Kumar Keshri, Waka Nakanishi, Atsuro Takai, Tomoya Ishizuka, Takahiko Kojima, Masayuki Takeuchi

研究成果: Article査読

5 被引用数 (Scopus)

抄録

The design and synthesis of a tweezer-shaped naphthalenediimide (NDI)–anthracene conjugate (2NDI) are reported. In the structure of the closed form (πNDI⋅⋅⋅πNDI stack) of 2NDI, which was elucidated by single-crystal XRD, the existence of C−H⋅⋅⋅O hydrogen bonding involving the nearest carbonyl oxygen atom of an NDI unit was suggested. The tunability of πNDI⋅⋅⋅πNDI interactions was studied by means of UV/Vis absorption, fluorescence and NMR spectroscopy and molecular modelling. This revealed that the πNDI⋅⋅⋅πNDI interactions in 2NDI affect the absorption and emission properties depending on the temperature. Furthermore, in polar solvents, 2NDI prefers the stronger πNDI⋅⋅⋅πNDI stack, whereas the πNDI⋅⋅⋅πNDI interaction is diminished in nonpolar solvents. Importantly, the conformational variations of 2NDI can be reversibly switched by variation in temperature, and this suggests potential application for fluorogenic molecular switches upon temperature changes.

本文言語English
ページ(範囲)13288-13294
ページ数7
ジャーナルChemistry - A European Journal
26
58
DOI
出版ステータスPublished - 2020 10月 15
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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