Liu, J.; Gao, X.; Niu, Q.; Jin, M.; Wang, Y.; Alshahrani, T.; Sun, H.-L.; Chen, B.; Li, Z.; Li, P. An Acid Responsive Fluorescent Molecule for Erasable Anti-Counterfeiting. Preprints2024, 2024080049. https://doi.org/10.20944/preprints202408.0049.v1
APA Style
Liu, J., Gao, X., Niu, Q., Jin, M., Wang, Y., Alshahrani, T., Sun, H. L., Chen, B., Li, Z., & Li, P. (2024). An Acid Responsive Fluorescent Molecule for Erasable Anti-Counterfeiting. Preprints. https://doi.org/10.20944/preprints202408.0049.v1
Chicago/Turabian Style
Liu, J., Zhiqiang Li and Peng Li. 2024 "An Acid Responsive Fluorescent Molecule for Erasable Anti-Counterfeiting" Preprints. https://doi.org/10.20944/preprints202408.0049.v1
Abstract
A tetraphenylethylene-derived compound, TPEPhDAT, has been prepared by successive Suzuki-Miyaura coupling and ring-closing reactions. This compound exhibits aggregation-induced emission (AIE) properties in the DMSO/MeOH system, with a fluorescence emission intensity in the aggregated state that is 5-fold higher than that of its counterpart in a dilute solution. Moreover, the diaminotriazine structure of the molecule is a good acceptor of protons, and thus the TPEPhDAT molecule exhibits acid-responsive fluorescence. TPEPhDAT was protonated by trifluoroacetic acid (TFA), leading to a fluorescence quenching, which was reversibly restored by treatment with ammonia (On-Off switch). Time-dependent density functional theory (TDDFT) computational studies have shown that protonation enhances the electron-withdrawing capacity of the triazine nucleus and reduces the bandgap, producing a more intense intramolecular charge transfer (ICT), thus leading to fluorescence quenching. MeOH can easily remove the protonated TPEPhDAT, and this acid-induced discolouration and erasable property can be applied in anti-counterfeiting.
Chemistry and Materials Science, Materials Science and Technology
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