Novel fluorescent Schiff bases as Al3+ sensors with high selectivity and sensitivity, and their bioimaging applications

Berrones‐Reyes, Jessica C.; Muñoz‐Flores, Blanca M.; Gómez-Treviño, Alberto; Treto‐Suárez, Manuel A.; Páez‐Hernández, Dayán; Schott, Eduardo; Zárate, Ximena; Jiménez-Pérez, Vı́ctor M.

doi:10.1016/j.matchemphys.2019.05.035

Cited by 37 publications

(27 citation statements)

References 49 publications

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“…As we reported in our recent works, the PET mechanisms in the molecular sensors based on Schiffbase can be correctly explained considering the relative energies of S 0 and S 1 electronic states of the interacting system [28,29,62,63]. Based on these results, for the best of our knowledge, the optimized geometry of the S 1 electronic state of Cd-MOF/pNA was employed for the first time to compute the excitations that constitute the emission spectrum and therefore go further the sensing mechanism.…”

Section: The Sensing Mechanism Of 4-nitraniline (Pna)supporting

confidence: 57%

“…To gain a deeper understanding of the turn-off fluorescence mechanism, we explored the optical properties of Cd-MOF and 5,5'-((thiophene-2,5dicarbonyl)bis(azanediyl))diisophthalic acid, ligand, we named as Linker, and Cd-MOF/analyte systems that were simulated via TD-DFT approach. In our previous studies, we verified the importance of considering the geometry of both the S 0 and the excited states (such as S 1 or T 1 ) to arrive at a robust interpretation of the sensing mechanisms [29,28,62,63]. Therefore, the optical spectra, i.e., absorption and emission of Cd-MOF were simulated, taking the optimized structures of the S 0 and S 1 states, respectively, as inputs in the TD-DFT calculations.…”

Section: Optical Properties Of Cd-mofmentioning

confidence: 70%

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Insights into the selective sensing mechanism of a luminescent Cd(II)-based MOF chemosensor toward NACs: roles of the host–guest interactions and PET processes

et al. 2021

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The structural and photophysical properties of the [Cd 2 (H 2 L) 2 (H 2 O) 5 ].5H 2 O (where H 4 L is the ligand 5,5'-((thiophene-2,5-dicarbonyl)bis(azanediyl))diisophthalic acid labeled as Cd-MOF), as well as the elucidation of the selective turn-off luminescent sensing mechanism toward 4-nitroaniline (pNA) were addressed, using quantum chemical methods. To reach this aim, the structures of the ground state (S 0 ) and first excited state (S 1 ) Cd-MOF/analyte system were assessed. We found that after the interaction a photoinduced electron transfer (PET) from the Cd-MOF to pNA is responsible for the fluorescence quenching in this system. For this purpose, a study was performed based on TD-DFT and multireference calculations to corroborate that an excited state exists with the adequate electronic configuration for PET process in the interacting system Cd-MOF/analyte. Intermolecular interaction between the Cd-MOF and analyte was studied by means of Morokuma-Ziegler energy decomposition analysis, natural

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Section: The Sensing Mechanism Of 4-nitraniline (Pna)supporting

confidence: 57%

Section: Optical Properties Of Cd-mofmentioning

confidence: 70%

Insights into the selective sensing mechanism of a luminescent Cd(II)-based MOF chemosensor toward NACs: roles of the host–guest interactions and PET processes

et al. 2021

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“…Enlightened by our previous work, a novel Schiff base fluorescent probe (E)-4-(benzo[d]thiazol-2-yl)-2-(((2-hydroxyphenyl)imino)methyl)-6-methoxyphenol (BHMMP) was easily synthesized and systematically investigated (Scheme 1), presenting a turn-on fluorescent response towards Al 3+ , which was ascribed to the inhibition of C=N isomerization and photo-induced electron transfer (PET) processes. A comparison of the probe BHMMP with the ones with the similar group was provided in Table S1 [45][46][47][48][49][50][51]. The unique advantages of BHMMP showed high sensitivity, good water solubility, significant recognition signal, and excellent potential application capabilities.…”

Section: Introductionmentioning

confidence: 99%

A Significant Fluorescence Turn-On Probe for the Recognition of Al3+ and Its Application

et al. 2022

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An easy prepared probe, BHMMP, was designed and synthesized, which displayed a significant fluorescence enhancement (over 38-fold) and obvious color change in the recognition of Al3+. The binding ratio of probe BHMMP to Al3+ was determined as 1:1, according to Job plot. The binding mechanism was fully clarified by the experiments, such as FT-IR spectrum, ESI–MS analysis, and 1H NMR titration. A DFT study further confirmed the binding mode of BHMMP to Al3+. The limit of detection (LOD) for Al3+ was determined as low as 0.70 µM, based on the fluorescence titration of BHMMP. Moreover, the results from real sample experiments, including real water samples, test papers, and cell images, well-demonstrated that BHMMP was capable of sensing Al3+ in environmental and biological systems.

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“…In this framework, optical chemosensors are simple devices used for continuous monitoring [4][5][6] of metal ions in situ and in vivo [7][8][9][10] since the optical properties, like the luminescence, can be changed upon the interaction with the analyte leading to a Chelation Enhanced Fluorescence (CHEF) [11,12] or a fluorescence quenching effect (CHEQ). [13][14][15] These effects are determined by a series of transduction mechanisms [16,17] based on Energy Transfer (ET) [18][19][20][21] and Charge Transfer (CT).…”

Section: Introductionmentioning

confidence: 99%

Understanding the Deactivating/Activating Mechanisms in Three Optical Chemosensors Based on Crown Ether with Na⁺/K⁺ Selectivity Using Quantum Chemical Tools

et al. 2022

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The optical properties and transduction mechanisms in three reported optical chemosensors based on crown ether with selectivity turn‐on luminescence toward Na+ over K+, were investigated using Density Functional Theory/Time‐Dependent Density Functional Theory (DFT/TD‐DFT). The analysis of the structural stability of the conformers enables us to understand the optical properties of the sensors and their selectivity toward Na+. The UV‐Vis absorption and the radiative channels of the adiabatic S1 excited state were assessed. In these reported sensors, the Photoinduced Electron Transfer (PET) from the nitrogen and the oxygen (O‐atoms of the substituted N‐phenylaza group) lone pairs to fluorophore groups lead to a nonradiative deactivation process in the fluorophore to p‐conjugated anilino‐1,2,3‐triazol ionophore. This Intramolecular Charge Transfer (ICT) deactivation produced the luminescence quenching in the free sensors and K+/C1 complexes. The Na+/sensor interaction produced a Chelation Enhanced Fluorescence (CHEF) due to the inhibition of the PET and ICT, which was confirmed via the calculated oscillator strength of the emission process. The K+/sensor interaction displayed the possibility of PET in C3; however, this fact was inconclusive to affirm the quenching of luminescence, the CHEF in C2 and C3 and the selectivity toward Na+ over K+ in these systems. For this reason, simulation of the absorption and emissions spectra (calculated oscillator strength), calculation of the kinetic parameters (in charge transfers and radiative deactivations process), analysis of the metal‐ligand interaction character, and the analysis of the structural stability of the conformers were determinant factors to understand the selectivity and the optical properties of these chemosensors. The results suggest that these theoretical tools can also be used to predict the optical properties and Na+/K+ selectivity of optical chemosensors.

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Novel fluorescent Schiff bases as Al3+ sensors with high selectivity and sensitivity, and their bioimaging applications

Cited by 37 publications

References 49 publications

Insights into the selective sensing mechanism of a luminescent Cd(II)-based MOF chemosensor toward NACs: roles of the host–guest interactions and PET processes

Insights into the selective sensing mechanism of a luminescent Cd(II)-based MOF chemosensor toward NACs: roles of the host–guest interactions and PET processes

A Significant Fluorescence Turn-On Probe for the Recognition of Al3+ and Its Application

Understanding the Deactivating/Activating Mechanisms in Three Optical Chemosensors Based on Crown Ether with Na⁺/K⁺ Selectivity Using Quantum Chemical Tools

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Novel fluorescent Schiff bases as Al3+ sensors with high selectivity and sensitivity, and their bioimaging applications

Cited by 37 publications

References 49 publications

Insights into the selective sensing mechanism of a luminescent Cd(II)-based MOF chemosensor toward NACs: roles of the host–guest interactions and PET processes

Insights into the selective sensing mechanism of a luminescent Cd(II)-based MOF chemosensor toward NACs: roles of the host–guest interactions and PET processes

A Significant Fluorescence Turn-On Probe for the Recognition of Al3+ and Its Application

Understanding the Deactivating/Activating Mechanisms in Three Optical Chemosensors Based on Crown Ether with Na+/K+ Selectivity Using Quantum Chemical Tools

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Product

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Understanding the Deactivating/Activating Mechanisms in Three Optical Chemosensors Based on Crown Ether with Na⁺/K⁺ Selectivity Using Quantum Chemical Tools