Ester-Aroyl-S,N-Ketene Acetals with Solid-State Luminescence: AIEgens from Sequential Three-Component...

Area of Science:

• Organic Chemistry
• Materials Science
• Photochemistry

Background:

• Di(hetero)aroyl dichlorides are versatile synthetic precursors.
• Merocyanine dyes are known for their optical properties.
• Aggregation-Induced Emission (AIE) is a phenomenon with growing applications.

Purpose of the Study:

• To develop a concise one-pot synthesis for ester-substituted aroyl-S,N-ketene acetals.
• To investigate the photophysical properties of the synthesized merocyanine dyes.
• To explore their potential as fluorescent reporters in aqueous environments.

Main Methods:

• One-pot three-component reaction of di(hetero)aroyl dichlorides, alcohols, and thiazolium salts.
• Spectroscopic analysis (UV-Vis, fluorescence) in various solvent mixtures.
• Investigation of aggregation-induced emission (AIE) in water/ethanol mixtures.
• Encapsulation into polystyrene nanoparticles.

Main Results:

• Successful synthesis of ester-substituted aroyl-S,N-ketene acetals under mild conditions.
• Synthesized merocyanine dyes exhibit charge-transfer absorption and solid-state fluorescence.
• Dyes display aggregation-induced emission (AIE) in water/ethanol mixtures, tunable by ester moiety.
• Encapsulation in nanoparticles significantly enhances fluorescence quantum yield (up to 30%).

Conclusions:

• The developed one-pot method provides efficient access to novel merocyanine dyes.
• These dyes show tunable AIE characteristics and potential for fluorescent sensing.
• Nanoparticle encapsulation enhances their utility as fluorescent reporters in aqueous media.