An AIEE Active Anthracene-Based Nanoprobe for Zn[sup.2+] and Tyrosine Detection Validated by Bioimaging Studies

Novel anthracene-based Schiff base derivative (4-(anthracen-9-ylmethylene) amino)-5-phenyl-4H-1,2,4-triazole-3-thiol; AT2) is synthesized and utilized as an aggregation-induced emission-enhancement (AIEE) active probe to detect Zn[sup.2+] and Tyrosine. Ultraviolet-visible absorption/photoluminescenc...

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Bibliographic Details
Published in:Chemosensors 2022-09, Vol.10 (10)
Main Authors: Shellaiah, Muthaiah, Thirumalaivasan, Natesan, Aazaad, Basheer, Awasthi, Kamlesh, Sun, Kien Wen, Wu, Shu-Pao, Lin, Ming-Chang, Ohta, Nobuhiro
Format: Article
Language:English
Subjects:
Phenols
Schiff bases
Tyrosine
Zinc
Zinc compounds
Online Access:Get full text
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Summary:Novel anthracene-based Schiff base derivative (4-(anthracen-9-ylmethylene) amino)-5-phenyl-4H-1,2,4-triazole-3-thiol; AT2) is synthesized and utilized as an aggregation-induced emission-enhancement (AIEE) active probe to detect Zn[sup.2+] and Tyrosine. Ultraviolet-visible absorption/photoluminescence (UV-vis/PL) spectroscopy studies on the AIEE property of AT2 (in ethanol) with increasing water fractions (fw: 0–97.5%) confirm the J-type aggregation. Excellent sensor selectivity of AT2 to Zn[sup.2+] and its reversibility with Tyrosine are demonstrated with PL interrogations. 2:1 and 1:1 stoichiometry and binding sites of AT2-Zn[sup.2+] and Tyrosine-Zn[sup.2+] complexes are elucidated from Job plots, HR-mass, and [sup.1] H-NMR results. Nanomolar-level detection limits (LODs) of Zn[sup.2+] (179 nM) and Tyrosine (667 nM) and association constants (K[sub.a] s) of 2.28 × 10[sup.−6] M[sup.−2] (for AT2-Zn[sup.2+] ) and 1.39 × 10[sup.−7] M[sup.−1] (for Tyrosine-Zn[sup.2+] ) are determined from standard deviation and linear fittings. Nanofiber formation in AIEE and aggregated/dispersed nanoparticles in the presence of the Zn[sup.2+] /Tyrosine are supported by scanning-electron microscope (SEM), transmission-electron microscope (TEM), atomic-force microscope (AFM), and dynamic-light scattering (DLS) investigations. Density-functional theory (DFT) studies confirm an “On-Off” twisted intramolecular charge transfer/photo-induced electron transfer (TICT/PET) and “On-Off-On” PET mechanisms for AIEE and sensors, respectively. B16-F10 cellular and zebrafish imaging are conducted to support the applications of AIEE and sensors.
ISSN:2227-9040
DOI:10.3390/chemosensors10100381