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- Title
Selective Conversion of P=O-Bridged Rhodamines into P=O-Rhodols: Solvatochromic Near-Infrared Fluorophores.
- Authors
Grzybowski, Marek; Taki, Masayasu; Yamaguchi, Shigehiro
- Abstract
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 (Δ λ=125 nm; >3600 cm−1) upon changing the solvent from toluene to water, whereas the emission is shifted less drastically (Δ λ=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.
- Subjects
RHODAMINES; PHOSPHINE oxides; FLUOROPHORES; DEAMINATION; XANTHENE dyes
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 53, p13028
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201703456