Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 53, Pages 13028-13032Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201703456
Keywords
near infrared fluorophores; phosphorus; photostability; rhodol; solvatochromism
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Funding
- JSPS KAKENHI [16K13949, 16K13097]
- World Premier International Research Center (WPI) Initiative, Japan
- JSPS for a postdoctoral fellowship
- Grants-in-Aid for Scientific Research [16K13949, 15F15761, 16K13097] Funding Source: KAKEN
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The substitution of an oxygen atom in rhodols with a phosphine oxide (P=O) moiety affords P=O-bridged rhodols as a new type of near-infrared (NIR) fluorophore. This compound class can be readily accessed upon exposure of the corresponding rhodamines to aqueous basic conditions. The electron-withdrawing effect of the P=O group facilitates the hydrolytic deamination, and, moreover, prolonged exposure to aqueous basic conditions generates P=O-bridged fluoresceins, that is, a series of three P=O-bridged xanthene dyes is available in one simple operation. The P=O-bridged rhodols show significant bathochromic shifts of the longest-wavelength absorption maximum (Delta lambda = 125 nm; > 3600 cm(-1)) upon changing the solvent from toluene to water, whereas the emission is shifted less drastically (Delta lambda = 70 nm; 1600 cm @ 1). The hydrogen bonding between the P=O and C=O groups with protic solvents results in substantial stabilization of the LUMO level, which is responsible for the solvatochromism.
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