TY - JOUR
T1 - Pyrene-Based AIEE Active Nanoprobe for Zn2+and Tyrosine Detection Demonstrated by DFT, Bioimaging, and Organic Thin-Film Transistor
AU - Shellaiah, Muthaiah
AU - Chen, Yu Ting
AU - Thirumalaivasan, Natesan
AU - Aazaad, Basheer
AU - Awasthi, Kamlesh
AU - Sun, Kien Wen
AU - Wu, Shu Pao
AU - Lin, Ming-Chang
AU - Ohta, Nobuhiro
N1 - Publisher Copyright:
©
PY - 2021/6/23
Y1 - 2021/6/23
N2 - The development of aggregation-induced emission enhancement (AIEE) active nanoprobes without any synthetic complication for solution-state and organic thin-film transistor (OTFT)-based sensory applications is still a challenging task. In this study, the novel pyrene-incorporated Schiff base (5-phenyl-4-((pyren-1-ylmethylene)amino)-4H-1,2,4-triazole-3-thiol; PT2) with an AIEE property was synthesized via a one-pot reaction and was reported for detecting Zn2+ and tyrosine in the solution state and OTFT. In the AIEE studies of PT2 (in CH3CN) at various water fractions (fw: 0-97.5%), the existence of J-aggregation, crystalline changes, and nanofibers formation was confirmed by ultraviolet absorption/photoluminescence (UV/PL) spectroscopy, powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), atomic force microscopy (AFM), and dynamic-light scattering (DLS) techniques. Similarly, PT2-based Zn2+ detection and sensory reversibility with tyrosine were demonstrated by UV/PL studies with evidence related to crystalline/nanolevel changes in PXRD, SEM, TEM, AFM, and DLS data. Distinct decay profiles associated with the AIEE and sensory responses of PT2 were observed in time-resolved photoluminescence spectra. From the standard deviation and linear fittings of PL titrations, detection limits (LODs) of the Zn2+ with PT2 and the tyrosine with PT2-Zn2+ were estimated as 0.79 and 45 nM, respectively. High-resolution mass and 1H NMR results confirmed 2:1 and 1:1 stoichiometry and binding sites of PT2-Zn2+-PT2∗ and tyrosine-Zn2+ complexes. Moreover, the values of association constants determined by linear fittings were 4.205 × 10-7 and 1.73 × 10-8 M-2, correspondingly. Optimization via the density functional theory disclosed the binding sites and suppression of twisted intramolecular charge transfer/photoinduced electron transfer (TICT/PET) as well as the involvement of restricted intramolecular rotation in the AIEE and PET "ON-OFF-ON"mechanisms in the Zn2+ and tyrosine sensors. Results from the B16-F10 cellular and zebrafish imaging of AIEE, Zn2+, and tyrosine sensors further attested the applicability of PT2 in biological samples. Finally, the PT2 and pentacene-incorporated OTFT devices were fabricated. The devices displayed more than 90% change in drain-source current when reacted with Zn2+ with an LOD of 5.46 μM but showed no response to tyrosine, thereby confirming the reversibility. Moreover, the OTFT devices also demonstrated Zn2+ ion detection in tap water and lake water samples.
AB - The development of aggregation-induced emission enhancement (AIEE) active nanoprobes without any synthetic complication for solution-state and organic thin-film transistor (OTFT)-based sensory applications is still a challenging task. In this study, the novel pyrene-incorporated Schiff base (5-phenyl-4-((pyren-1-ylmethylene)amino)-4H-1,2,4-triazole-3-thiol; PT2) with an AIEE property was synthesized via a one-pot reaction and was reported for detecting Zn2+ and tyrosine in the solution state and OTFT. In the AIEE studies of PT2 (in CH3CN) at various water fractions (fw: 0-97.5%), the existence of J-aggregation, crystalline changes, and nanofibers formation was confirmed by ultraviolet absorption/photoluminescence (UV/PL) spectroscopy, powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), atomic force microscopy (AFM), and dynamic-light scattering (DLS) techniques. Similarly, PT2-based Zn2+ detection and sensory reversibility with tyrosine were demonstrated by UV/PL studies with evidence related to crystalline/nanolevel changes in PXRD, SEM, TEM, AFM, and DLS data. Distinct decay profiles associated with the AIEE and sensory responses of PT2 were observed in time-resolved photoluminescence spectra. From the standard deviation and linear fittings of PL titrations, detection limits (LODs) of the Zn2+ with PT2 and the tyrosine with PT2-Zn2+ were estimated as 0.79 and 45 nM, respectively. High-resolution mass and 1H NMR results confirmed 2:1 and 1:1 stoichiometry and binding sites of PT2-Zn2+-PT2∗ and tyrosine-Zn2+ complexes. Moreover, the values of association constants determined by linear fittings were 4.205 × 10-7 and 1.73 × 10-8 M-2, correspondingly. Optimization via the density functional theory disclosed the binding sites and suppression of twisted intramolecular charge transfer/photoinduced electron transfer (TICT/PET) as well as the involvement of restricted intramolecular rotation in the AIEE and PET "ON-OFF-ON"mechanisms in the Zn2+ and tyrosine sensors. Results from the B16-F10 cellular and zebrafish imaging of AIEE, Zn2+, and tyrosine sensors further attested the applicability of PT2 in biological samples. Finally, the PT2 and pentacene-incorporated OTFT devices were fabricated. The devices displayed more than 90% change in drain-source current when reacted with Zn2+ with an LOD of 5.46 μM but showed no response to tyrosine, thereby confirming the reversibility. Moreover, the OTFT devices also demonstrated Zn2+ ion detection in tap water and lake water samples.
KW - AIEE, OTFT sensors
KW - bioimaging
KW - DFT optimization
KW - pyrene
KW - real applications
KW - Schiff base
UR - http://www.scopus.com/inward/record.url?scp=85108654864&partnerID=8YFLogxK
U2 - 10.1021/acsami.1c04744
DO - 10.1021/acsami.1c04744
M3 - Article
C2 - 34110776
AN - SCOPUS:85108654864
SN - 1944-8244
VL - 13
SP - 28610
EP - 28626
JO - ACS Applied Materials and Interfaces
JF - ACS Applied Materials and Interfaces
IS - 24
ER -