Development of chromic molecule that can change color and absorption/fluorescence wavelengths largely in response to external stimuli

Shinichiro Kamino, Masaru Tanioka, Daisuke Sawada

Research output: Contribution to journalReview article

1 Citation (Scopus)

Abstract

Aminobenzopyranoxanthene (ABPX) dye, developed by our group, exhibits two-step color change in solution through a spiro-ring opening/closing process in response to chemical stimuli such as acids, metal ions and phenols. Using this unique characteristic, we have developed ABPX-based colorimetric sensor that change color depending on Cu2+ concentration, enabling visualization by spectrophotometry and the naked eye. Furthermore, an efficient and practical method to prepare ABPX with various nitrogen-containing fused rings was developed. Using a simple acid-catalyzed reaction consisting of 1,3-diisopropoxybenzene and CH 3SO 3H, a variety of benzophenones gave ABPX directly in excellent yields. We discovered that ABPX is a new type of mechanochromic organic molecule with a large wavelength difference of fluorescence (near-IR/blue). 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 in response to mechanical grinding and exposure to the vapor of solvents.

Original languageEnglish
Pages (from-to)1066-1075
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume76
Issue number10
DOIs
Publication statusPublished - 2018

Keywords

  • Absorption
  • Aminobenzopyranoxanthene
  • Chromism
  • External stimuli
  • Fluorescence
  • Mechanochromisim
  • Organic dye
  • Rhodamine
  • Vapochromism
  • Xanthene dye

ASJC Scopus subject areas

  • Organic Chemistry

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