In situ electrochemical-ATR-FTIR spectroscopic studies on solution phase carboxylate radical anionsElectronic supplementary information (ESI) available: first derivative EPR spectra of radical anions. See http://www.rsc.org/suppdata/p2/b2/b206087f/

[reaction: see text] Alpha-tocopherol (alpha-TOH), the main oil component making up vitamin E, and its nonnatural solid 6-hydroxy-2,2,5,7,8-pentamethylchroman and 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid structurally related analogues were oxidized quantitatively with 2 mol equiv of NO+ SbF6(-) in CH3CN at 233 K to form phenoxonium cations (alpha-TO+ SbF6(-)) in a chemically reversible two-electron/one-proton process. Solution-phase infrared spectroscopy, 1H and 13C NMR spectroscopy, and corresponding theoretical calculations of the spectroscopic data using density-based and wave-function-based models support the identity of the remarkably stable phenoxonium cations. The presence of an oxygen atom in the para position to the hydroxyl group and the chromanol ring structure appear to be important factors in stabilization of the phenoxonium ions, which raises the interesting possibility that the cations play a crucial role in the mode of action of vitamin E in biological systems. Although the phenoxonium cations are reactive toward nucleophiles such as water, they may be moderately stable in the hydrophobic (lipophilic) environment where vitamin E is known to occur naturally.

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“…Apparatus. Solution-phase FTIR experiments were conducted utilizing a diamond composite attenuated total reflection (ATR) probe …”

Section: Methodsmentioning

confidence: 99%

Transformation of α-Tocopherol (Vitamin E) and Related Chromanol Model Compounds into Their Phenoxonium Ions by Chemical Oxidation with the Nitrosonium Cation

et al. 2005

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Edible Long‐Afterglow Photoluminescent Materials for Bioimaging

Shen,

Xie,

Sahoo

et al. 2024

Advanced Materials

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Confining luminophores into modified hydrophilic matrices or polymers is a straightforward and widely used approach for afterglow bioimaging. However, the afterglow quantum yield and lifetime of the related material remain unsatisfactory, severely limiting the using effect especially for deep‐tissue time‐resolved imaging. This fact largely stems from the dilemma between material biocompatibility and the quenching effect of water environment. We herein present an in situ metathesis promoted doping strategy, namely, mixing ∼10−3 weight ratio of organic‐emitter multicarboxylates with inorganic salt reactants, followed by metathesis reactions to prepare a series of hydrophilic but water‐insoluble organic‐inorganic doping afterglow materials. This strategy led to the formation of edible long‐afterglow photoluminescent materials with superior biocompatibility and excellent bioimaging effect. The phosphorescence quantum yield of the materials can reach dozens of percent (the highest case: 66.24%), together with the photoluminescent lifetime lasting for coupes of seconds. Specifically, a long‐afterglow barium meal formed by coronene salt emitter and BaSO4 matrix was applied into animal experiments by gavage, and bright stomach afterglow imaging was observed by instruments or mobile phone after ceasing the photoexcitation with deep tissue penetration. This strategy allows a flexible dosage of the materials during bioimaging, facilitating the development of real‐time probing and theranostic technology.This article is protected by copyright. All rights reserved

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Pyridines and their Benzo Derivatives: Structure

Harper

2008

Comprehensive Heterocyclic Chemistry III

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In situ electrochemical-ATR-FTIR spectroscopic studies on solution phase carboxylate radical anionsElectronic supplementary information (ESI) available: first derivative EPR spectra of radical anions. See http://www.rsc.org/suppdata/p2/b2/b206087f/

Cited by 16 publications

References 18 publications

Transformation of α-Tocopherol (Vitamin E) and Related Chromanol Model Compounds into Their Phenoxonium Ions by Chemical Oxidation with the Nitrosonium Cation

Transformation of α-Tocopherol (Vitamin E) and Related Chromanol Model Compounds into Their Phenoxonium Ions by Chemical Oxidation with the Nitrosonium Cation

Edible Long‐Afterglow Photoluminescent Materials for Bioimaging

Pyridines and their Benzo Derivatives: Structure

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