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 language | English |
|---|---|
| Pages (from-to) | 975-986 |
| Number of pages | 12 |
| Journal | Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan |
| Volume | 139 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - Jan 1 2019 |
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Keywords
- aminobenzopyranoxanthene
- chromism
- organic π molecule
- rhodamine
- stimuli-responsive molecule
ASJC Scopus subject areas
- Pharmacology
- Pharmaceutical Science
Cite this
Development of External Stimuli-responsive Organic π Molecules and the Creation of Novel Photo-functions. / Kamino, Shinichiro.
In: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, Vol. 139, No. 7, 01.01.2019, p. 975-986.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Development of External Stimuli-responsive Organic π Molecules and the Creation of Novel Photo-functions
AU - Kamino, Shinichiro
PY - 2019/1/1
Y1 - 2019/1/1
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
UR - http://www.scopus.com/inward/record.url?scp=85069004165&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85069004165&partnerID=8YFLogxK
U2 - 10.1248/yakushi.19-00005
DO - 10.1248/yakushi.19-00005
M3 - Article
C2 - 31257255
AN - SCOPUS:85069004165
VL - 139
SP - 975
EP - 986
JO - Yakugaku Zasshi
JF - Yakugaku Zasshi
SN - 0031-6903
IS - 7
ER -