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Published on: June 10, 2021
Benzo[a]Phenoxazine Derivatives as Fluorescent Disperse Dyes-Spectroscopic Characterization and Application
Magda Adamczyk1,2, Aleksandra Grzelakowska1, Joanna Paluszkiewicz1
1Faculty of Chemistry, Institute of Polymer and Dye Technology, Lodz University of Technology, Lodz, Poland.
Summary
New benzo[a]phenoxazine disperse dyes offer vibrant red and orange fluorescence for polyester. These novel dyes exhibit excellent fluorescence quantum yields and high fastness properties, expanding options beyond limited existing fluorescent options.
Area of Science:
- Materials Science
- Organic Chemistry
- Textile Chemistry
Background:
- Limited availability of non-azo, red, and orange fluorescent disperse dyes.
- Existing options include coumarins, thioindigo, and naphthalimide derivatives.
- Need for novel fluorescent disperse dyes with improved properties.
Purpose of the Study:
- Synthesize and apply benzo[a]phenoxazine derivatives as novel red and orange fluorescent disperse dyes for polyester.
- Evaluate the photochemical stability and fastness properties of these new dyes.
- Assess their potential as alternatives to existing limited fluorescent disperse dyes.
Main Methods:
- Synthesis of 6-substituted 9-nitro- and 9-amino-5H-benzo[a]phenoxazin-5-one derivatives.
- Application of dyes to polyester fabric using high-temperature pressure dyeing.
- Investigation of photochemical stability in acetonitrile solution.
- Measurement of chromaticity, luminance, fluorescence quantum yield, and fastness properties (sublimation, washing, rubbing).
Main Results:
- Successfully synthesized and applied benzo[a]phenoxazine derivatives to polyester, yielding red and orange fluorescence.
- All dyed fabrics exhibited fluorescence quantum yields exceeding 20%.
- Dyes demonstrated strong resistance to sublimation (4/5), washing (4/5), and rubbing (4/5).
- Photochemical stability varied, with 9-nitro-5H-benzo[a]phenoxazin-5-one (2a) showing lower photostability and lightfastness compared to others.
Conclusions:
- Benzo[a]phenoxazine derivatives are effective red and orange fluorescent disperse dyes for polyester.
- These novel dyes offer high fluorescence quantum yields and excellent fastness properties.
- They represent a promising alternative to the limited range of currently available fluorescent disperse dyes.
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