One-Step Transformations from ACQ Luminogens to DSEgens via the Boc Protection Process

Area of Science:

• Materials Science
• Organic Chemistry
• Photophysics

Background:

• Dual-state emission luminogens (DSEgens) are advanced materials emitting light in both solution and solid states.
• Their applications span chemical sensing, biological imaging, and organic electronics.
• Developing new DSEgens with tailored properties is crucial for technological advancement.

Purpose of the Study:

• To synthesize and characterize novel rofecoxib derivatives with dual-state emission properties.
• To investigate the photophysical behavior and structure-property relationships of these compounds.
• To explore the potential applications of the developed DSEgens in imaging.

Main Methods:

• Synthesis of rofecoxib derivatives (ROIN and ROIN-B).
• Photophysical property investigation using experimental techniques and theoretical calculations.
• Single X-ray diffraction analysis to elucidate structural and fluorescent behavior.
• Cellular imaging studies in HeLa cells.

Main Results:

• ROIN derivative exhibits classical aggregation-caused quenching (ACQ).
• ROIN-B derivative, modified with a tert-butoxycarbonyl group, displays significant dual-state emission (DSE) properties.
• The transformation from ACQ to DSE was clearly understood through structural analysis.
• ROIN-B demonstrated reversible mechanofluorochromism and specific lipid droplet imaging in cells.

Conclusions:

• A precise molecular design strategy was proposed for creating new DSEgens.
• ROIN-B serves as a novel DSEgen with potential for advanced imaging applications.
• This study provides valuable insights for the future development of DSEgens.