Development of External Stimuli-responsive Organic π Molecules and the Creation of Novel Photo-functions

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Abstract

We have found that the spiro form of aminobenzopyranoxanthene (ABPX) exhibits dual solvatochromic and nanoaggregate fluorescence in organic solvents by spectrophotometric and theoretical analyses. The dual fluorescence properties of ABPX were adjustable in response to water content, and served as a new detection principal for naked-eye visualization (above 0.5 wt%) and quantification (0.010-0.125 wt%) of water in tetrahydrofuran. In investigating the optical properties of a dicationic form of ABPX, ABPX containing linear n-alkyl chains at amino groups were then synthesized. These ABPX exhibited fluorescence emission in the far-red and NIR wavelength regions, and we noted an increased fluorescence quantum efficiency with increasing n-alkyl chain length. To further improve the fluorescence quantum yields, we have designed and synthesized ABPX with different nitrogen-containing fused rings. It was kinetically demonstrated that the structurally rigid conjugation of the xanthene moiety is an effective molecular design for the drastic enhancement of fluorescence emission efficiency.

Original languageEnglish
Pages (from-to)975-986
Number of pages12
JournalYakugaku zasshi : Journal of the Pharmaceutical Society of Japan
Volume139
Issue number7
DOIs
Publication statusPublished - Jan 1 2019

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Fluorescence
Xanthenes
Water
Nitrogen

Keywords

  • aminobenzopyranoxanthene
  • chromism
  • organic π molecule
  • rhodamine
  • stimuli-responsive molecule

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

Cite this

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title = "Development of External Stimuli-responsive Organic π Molecules and the Creation of Novel Photo-functions",
abstract = "We have found that the spiro form of aminobenzopyranoxanthene (ABPX) exhibits dual solvatochromic and nanoaggregate fluorescence in organic solvents by spectrophotometric and theoretical analyses. The dual fluorescence properties of ABPX were adjustable in response to water content, and served as a new detection principal for naked-eye visualization (above 0.5 wt{\%}) and quantification (0.010-0.125 wt{\%}) of water in tetrahydrofuran. In investigating the optical properties of a dicationic form of ABPX, ABPX containing linear n-alkyl chains at amino groups were then synthesized. These ABPX exhibited fluorescence emission in the far-red and NIR wavelength regions, and we noted an increased fluorescence quantum efficiency with increasing n-alkyl chain length. To further improve the fluorescence quantum yields, we have designed and synthesized ABPX with different nitrogen-containing fused rings. It was kinetically demonstrated that the structurally rigid conjugation of the xanthene moiety is an effective molecular design for the drastic enhancement of fluorescence emission efficiency.",
keywords = "aminobenzopyranoxanthene, chromism, organic π molecule, rhodamine, stimuli-responsive molecule",
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N2 - We have found that the spiro form of aminobenzopyranoxanthene (ABPX) exhibits dual solvatochromic and nanoaggregate fluorescence in organic solvents by spectrophotometric and theoretical analyses. The dual fluorescence properties of ABPX were adjustable in response to water content, and served as a new detection principal for naked-eye visualization (above 0.5 wt%) and quantification (0.010-0.125 wt%) of water in tetrahydrofuran. In investigating the optical properties of a dicationic form of ABPX, ABPX containing linear n-alkyl chains at amino groups were then synthesized. These ABPX exhibited fluorescence emission in the far-red and NIR wavelength regions, and we noted an increased fluorescence quantum efficiency with increasing n-alkyl chain length. To further improve the fluorescence quantum yields, we have designed and synthesized ABPX with different nitrogen-containing fused rings. It was kinetically demonstrated that the structurally rigid conjugation of the xanthene moiety is an effective molecular design for the drastic enhancement of fluorescence emission efficiency.

AB - We have found that the spiro form of aminobenzopyranoxanthene (ABPX) exhibits dual solvatochromic and nanoaggregate fluorescence in organic solvents by spectrophotometric and theoretical analyses. The dual fluorescence properties of ABPX were adjustable in response to water content, and served as a new detection principal for naked-eye visualization (above 0.5 wt%) and quantification (0.010-0.125 wt%) of water in tetrahydrofuran. In investigating the optical properties of a dicationic form of ABPX, ABPX containing linear n-alkyl chains at amino groups were then synthesized. These ABPX exhibited fluorescence emission in the far-red and NIR wavelength regions, and we noted an increased fluorescence quantum efficiency with increasing n-alkyl chain length. To further improve the fluorescence quantum yields, we have designed and synthesized ABPX with different nitrogen-containing fused rings. It was kinetically demonstrated that the structurally rigid conjugation of the xanthene moiety is an effective molecular design for the drastic enhancement of fluorescence emission efficiency.

KW - aminobenzopyranoxanthene

KW - chromism

KW - organic π molecule

KW - rhodamine

KW - stimuli-responsive molecule

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