Phenoxazine is a commonly used molecular building block, for example in optoelectronic applications and pharmaceuticals. However, it is highly susceptible to rapid photodegradation, especially in halogenated solvents. In the present study, we identify the degradation products in both halogenated and non-halogenated solvents by UV/Vis absorption, NMR spectroscopy and mass spectrometry. We also propose a substitution strategy aimed at effectively suppressing the high photoreactivity. Kinetic studies show that the quantum yield of photodegradation φ differs by a factor of more than 1000 between trisubstituted derivatives and N-substituted phenoxazine.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/cphc.202400506 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Photostability of Phenoxazine Derivatives.
Chemphyschem
November 2024
Institute of Organic Chemistry III-Macromolecular Chemistry and Organic Materials, Ulm University, 89081, Ulm, Germany.
Phenoxazine is a commonly used molecular building block, for example in optoelectronic applications and pharmaceuticals. However, it is highly susceptible to rapid photodegradation, especially in halogenated solvents. In the present study, we identify the degradation products in both halogenated and non-halogenated solvents by UV/Vis absorption, NMR spectroscopy and mass spectrometry.
View Article and Find Full Text PDFNew coumarin- and phenoxazine-based fluorescent probes for live-cell STED nanoscopy.
Eur Biophys J
July 2019
Jožef Stefan Institute, Jamova 39, 1000, Ljubljana, Slovenia.
The potential of live-cell stimulated emission depletion (STED) nanoscopy has not yet been fully exploited. Currently, the main limitation is the small number of fluorophores and probes that can sustain high light intensity/high dose employed in STED. Namely, fluorophores suitable for STED nanoscopy must be bright and highly photostable and exhibit a large Stokes shift.
View Article and Find Full Text PDFNile Red and Nile Blue: Applications and Syntheses of Structural Analogues.
Chemistry
September 2016
Department of Chemistry, Georgia State University, Atlanta, GA, 30302, USA.
Nile red and Nile blue are highly fluorescent and photostable organic dyes from the benzo[a]phenoxazine family. They have been used as histological stains for imaging lysosomes and lipids in vitro. The dyes' high quantum yields and solvent-dependent optical properties make them ideal scaffolds for the development of pH probes and local polarity indicators.
View Article and Find Full Text PDF5,9-Diaminodibenzo[a,j]phenoxazinium chloride: a rediscovered efficient long wavelength fluorescent dye.
J Fluoresc
March 2008
Rowland Institute at Harvard, Harvard University, 100 Edwin Land Blvd., Cambridge, MA 02142, USA.
We have evaluated the chemical, photophysical and photostability properties of 5,9-diaminodibenzo[a,j]phenoxazinium chloride, 3, and its bis-5,9-ethylamino analogue, 4, with the goal of determining if they have characteristics that are compatible with the requirements of a useful fluorescent probe. In order to gauge the potential utility of these fluorophores in biological and non-biological applications, these data were compared to those obtained for Oxazine 118, 1, and Cresyl Violet, 2, two well known fluorescent dyes that differ in molecular structure from the title dye 3 by having two or one fewer benzo moieties fused to a generic oxazine ring structure, respectively. The findings of this investigation show that 3, as well as bis-ethylamino analogue, 4, have fluorescent lifetimes, quantum yields and photostabilities that compare favorably with the lower order benchmark fluorophores 1 and 2.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!