Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene

Masaru Tanioka, Shinichiro Kamino, Atsuya Muranaka, Yousuke Ooyama, Hiromi Ota, Yoshinao Shirasaki, Jun Horigome, Masashi Ueda, Masanobu Uchiyama, Daisuke Sawada, Shuichi Enomoto

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Abstract

Mechanochromic organic molecules (MOMs) that exhibit a large difference of fluorescence wavelength between two states have important potential applications, but few such compounds are known. Here, we report a new MOM, cis-ABPX010, which shows switchable near-IR and blue fluorescence responses. Detailed spectrophotometric and single-crystal X-ray analyses revealed that the near-IR fluorescence is attributable to fluorescence from slip-stacked dimeric structures in crystals, while the blue fluorescence is attributable to fluorescence from the monomer. Switching between the two is achieved by dynamic structural interconversion between the two molecular packing arrangements in response to mechanical grinding and solvent vapor-fuming.

Original languageEnglish
Pages (from-to)6436-6439
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number20
DOIs
Publication statusPublished - May 27 2015

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Tanioka, M., Kamino, S., Muranaka, A., Ooyama, Y., Ota, H., Shirasaki, Y., Horigome, J., Ueda, M., Uchiyama, M., Sawada, D., & Enomoto, S. (2015). Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene. Journal of the American Chemical Society, 137(20), 6436-6439. https://doi.org/10.1021/jacs.5b00877