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

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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 - Jan 1 2018

Fingerprint

Fluorescence
Color
Wavelength
Molecules
Benzophenones
Acids
Structural dynamics
Spectrophotometry
Metal ions
Coloring Agents
Nitrogen
Visualization
Monomers
Vapors
Single crystals
X rays
Crystals
Sensors

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Development of chromic molecule that can change color and absorption/fluorescence wavelengths largely in response to external stimuli",
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.",
keywords = "Absorption, Aminobenzopyranoxanthene, Chromism, External stimuli, Fluorescence, Mechanochromisim, Organic dye, Rhodamine, Vapochromism, Xanthene dye",
author = "Shinichiro Kamino and Masaru Tanioka and Daisuke Sawada",
year = "2018",
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language = "English",
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T1 - Development of chromic molecule that can change color and absorption/fluorescence wavelengths largely in response to external stimuli

AU - Kamino, Shinichiro

AU - Tanioka, Masaru

AU - Sawada, Daisuke

PY - 2018/1/1

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N2 - 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.

AB - 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.

KW - Absorption

KW - Aminobenzopyranoxanthene

KW - Chromism

KW - External stimuli

KW - Fluorescence

KW - Mechanochromisim

KW - Organic dye

KW - Rhodamine

KW - Vapochromism

KW - Xanthene dye

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