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Author Spotlight: Quantitative Characterization of Liquid Photosensitive Bioink Properties for Continuous Digital Light Processing Based Printing
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An Acid-Responsive Fluorescent Molecule for Erasable Anti-Counterfeiting.

Jiabao Liu1, Xiangyu Gao2, Qingyu Niu1

  • 1School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, China.

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|September 28, 2024
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Summary

A novel tetraphenylethylene (TPE) derivative, TPEPhDAT, shows aggregation-induced emission enhancement (AIEE) and acid-responsive fluorescence. This molecule can be used for erasable anti-counterfeiting applications due to its reversible fluorescence quenching.

Keywords:
aggregation-induced emission enhancement (AIEE)anti-counterfeitingdiaminotriazine (DAT)stimuli-responsive luminescencetetraphenylethylene (TPE)

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Aggregation-induced emission enhancement (AIEE) is a phenomenon where luminogens are non-emissive in solution but become highly fluorescent upon aggregation.
  • Tetraphenylethylene (TPE) derivatives are widely studied for their AIEE properties, finding applications in sensors, imaging, and optoelectronics.
  • Diaminotriazine (DAT) moieties can act as proton acceptors, enabling responsive fluorescence behavior.

Purpose of the Study:

  • To synthesize and characterize a novel TPE derivative, TPEPhDAT, incorporating a DAT unit.
  • To investigate the AIEE properties of TPEPhDAT in a DMSO/MeOH system.
  • To explore the acid-responsive fluorescence behavior of TPEPhDAT and its potential applications.

Main Methods:

  • Suzuki-Miyaura coupling and ring-closing reactions for synthesis of TPEPhDAT.
  • Spectroscopic analysis (fluorescence spectroscopy) to study AIEE and acid-responsiveness.
  • Time-dependent density functional theory (TDDFT) calculations to understand the photophysical mechanisms.

Main Results:

  • TPEPhDAT was successfully synthesized and demonstrated significant AIEE properties, with a 5-fold increase in fluorescence intensity upon aggregation.
  • The molecule exhibited acid-responsive fluorescence, with protonation by trifluoroacetic acid (TFA) causing fluorescence quenching.
  • The quenched fluorescence was reversibly restored by treatment with ammonia, indicating an 'on-off' switching capability. TDDFT studies revealed protonation-induced changes in electronic structure and conformation, potentially leading to a twisted intramolecular charge transfer (TICT) effect.
  • The acid-induced discoloration and erasable property were observed, suggesting potential for anti-counterfeiting applications.

Conclusions:

  • The synthesized TPEPhDAT derivative exhibits promising AIEE and acid-responsive fluorescence characteristics.
  • The reversible 'on-off' fluorescence switching and erasable property make TPEPhDAT a potential candidate for advanced anti-counterfeiting technologies.
  • Computational studies provide insights into the photophysical mechanisms governing the observed fluorescence behavior.