Aggregation-Induced Emission or Hydrolysis by Water? The Case of Schiff Bases in Aqueous Organic Solvents

Pramanik, Bapan; Das, Debapratim

doi:10.1021/acs.jpcc.7b12430

Cited by 46 publications

(30 citation statements)

References 40 publications

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“…From absorption spectral studies, it was strongly believed that J-type aggregation was formed in 70–90% water content for H 2 L with the evidence from decreasing absorption along with a red shift upon increasing the water content. The maximum emission at 520 nm with 90% water content is attributed to the aggregation effect but not due to hydrolysis. , The enhanced emission due to aggregation of H 2 L was also supported by the time-resolved photoluminescence (TRPL) experiment (Figure c). The decay lifetime for H 2 L increased with addition of water and reached maximum (2.17 ns) at 90% of water content (Table S1).…”

Section: Resultsmentioning

confidence: 60%

“…The maximum emission at 520 nm with 90% water content is attributed to the aggregation effect but not due to hydrolysis. 55,56 The enhanced emission due to aggregation of H 2 L was also supported by the time-resolved photoluminescence (TRPL) experiment (Figure 1c). The decay lifetime for H 2 L increased with addition of water and reached maximum (2.17 ns) at 90% of water content (Table S1).…”

Section: Aggregation-induced Emission Enhancement (Aiee)mentioning

confidence: 54%

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Solvent-Regulated Fluorimetric Differentiation of Al³⁺ and Zn²⁺ Using an AIE-Active Single Sensor

Das

Dolai²,

Dhara

et al. 2021

J. Phys. Chem. A

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The absence of d-orbital electrons or presence of full-filled d-orbital electrons in metal ions is a well-known Achilles' heel problem for the detection of these metal ions by a simple UV-visible study. For this reason, detection of metal ions such as Al 3+ with no d-orbital electrons or Zn 2+ with filled d-orbital electrons is a challenging task. Herein, we report a 2-naphthol-based fluorescent probe [1-((E)-((E)-(5-bromo-2-hydroxybenzylidene)hydrazono)methyl)naphthalen-2-ol] (H 2 L) that has been used to sense and discriminate Al 3+ and Zn 2+ via solvent regulation. The probe exhibits excellent selectivity and swift sensitivity toward Al 3+ in MeOH− water (9:1, v/v) and toward Zn 2+ in dimethyl sulfoxide (DMSO)−water (9:1, v/v) among various metal ions. The respective detection limit is found to be 9.78 and 3.65 μM. The sensing mechanism is attributed to multiple processes, viz., the inhibition of photo-induced electron transfer (PET) along with the introduction of chelation-enhanced emission (CHEF) and excited-state intramolecular proton transfer (ESIPT) inhibition, which are experimentally well verified by UV−vis absorption spectroscopy, emission spectroscopy, and NMR spectroscopy. The probe shows aggregation-induced emissive (AIE) response in ≥70% aqueous media as well as in the solid state. The experimental results are well corroborated by time-resolved photoluminescence (TRPL) and density functional theory (DFT) calculations. An advanced-level OR-AND-NOT logic gate has been constructed from a different chemical combinational input and emission output. The reversible recognition of both Al 3+ in MeOH−water (9:1, v/v) and Zn 2+ in DMSO−water (9:1, v/v) is also ascertained in the presence of Na 2 EDTA, enabling the construction of a molecular memory device. The probe H 2 L also detects intracellular Al 3+ /Zn 2+ ions in Hela cells. Altogether, our fundamental findings will pave the way for designing and synthesis of unique chemosensors that could be used for cell imaging studies as well as constructing molecular logic gates.

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Section: Resultsmentioning

confidence: 60%

Section: Aggregation-induced Emission Enhancement (Aiee)mentioning

confidence: 54%

Solvent-Regulated Fluorimetric Differentiation of Al³⁺ and Zn²⁺ Using an AIE-Active Single Sensor

Das

Dolai²,

Dhara

et al. 2021

J. Phys. Chem. A

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“…They include various mechanisms responsible for their use, such as photoinduced electron transport inhibition [ 12 ], compound hydrolysis [ 13 ], aggregation-induced emission (AIE) [ 2 , 14 ], bioreductive fluorescent sensors [ 15 ], fluorogenic substrates for glutathione S-transferase (GST) activity [ 16 ], or the formation of metal complexes, i.e., Zn 2+ [ 17 , 18 , 19 ], Cu 2+ [ 20 , 21 ], Fe 3+ [ 22 , 23 ]. Nevertheless, the use of imines in biological research is associated with the possibility of hydrolysis of these compounds [ 24 ]. However, the imines described in the literature, which underwent hydrolysis and had a significant impact on the properties, most often contained a unit with an imine bond in their structures, capable of complexing ions [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

Luminescence and Electrochemical Activity of New Unsymmetrical 3-Imino-1,8-naphthalimide Derivatives

et al. 2021

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A new series of 1,8-naphtalimides containing an imine bond at the 3-position of the naphthalene ring was synthesized using 1H, 13C NMR, FTIR, and elementary analysis. The impact of the substituent in the imine linkage on the selected properties and bioimaging of the synthesized compounds was studied. They showed a melting temperature in the range of 120–164 °C and underwent thermal decomposition above 280 °C. Based on cyclic and differential pulse voltammetry, the electrochemical behavior of 1,8-naphtalimide derivatives was evaluated. The electrochemical reduction and oxidation processes were observed. The compounds were characterized by a low energy band gap (below 2.60 eV). Their photoluminescence activities were investigated in solution considering the solvent effect, in the aggregated and thin film, and a mixture of poly(N-vinylcarbazole) (PVK) and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) (50:50 wt.%). They demonstrated low emissions due to photoinduced electron transport (PET) occurring in the solution and aggregation, which caused photoluminescence quenching. Some of them exhibited light emission as thin films. They emitted light in the range of 495 to 535 nm, with photoluminescence quantum yield at 4%. Despite the significant overlapping of its absorption range with emission of the PVK:PBD, incomplete Förster energy transfer from the matrix to the luminophore was found. Moreover, its luminescence ability induced by external voltage was tested in the diode with guest–host configuration. The possibility of compound hydrolysis due to the presence of the imine bond was also discussed, which could be of importance in biological studies that evaluate 3-imino-1,8-naphatalimides as imaging tools and fluorescent materials for diagnostic applications and molecular bioimaging.

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“…The main goal of this research was to obtain a compound that has an imine bond cleavage in acidic conditions, but that is stable in a cytosol or other organelles. Therefore, our attention was focused on the possibility of inducing a hydrolysis process in aqueous conditions 27 . For that purpose, we prepared a set of samples that contained 25% water and 75% of ethanol which were measured using the HPLC method after 5, 15, 30, and 60 minutes to determine the progress of decomposition at given time.…”

Section: Resultsmentioning

confidence: 99%

Acid selective pro-dye for cellular compartments

Czaplińska

Malarz

Mrozek-Wilczkiewicz

et al. 2019

Sci Rep

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A novel pro-dye approach for the acid-selective staining of the subcellular compartments for better permeability and selectivity was applied. The designed sensor has suitable physicochemical properties such as a large Stokes shift and a long-lived intracellular fluorescence. The Schiff base fragment was used for the acid-sensitive release of a fluorophore without affecting the overall stability of the biological systems. Due to the presence of an imine bond in its structure and its unique fluorescent properties, it can be presented as a “pro-dye” for acidic structures such as lysosomes. As a result of an imine bond cleavage, a new fluorescent compound is released, whose substantially shifted excitation and emission wavelengths enable a more selective and effective imaging of lysosomes and endosomes. The presented report provides the chemical, physicochemical and optical profiles as well as biological assays and theoretical calculations.

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Aggregation-Induced Emission or Hydrolysis by Water? The Case of Schiff Bases in Aqueous Organic Solvents

Cited by 46 publications

References 40 publications

Solvent-Regulated Fluorimetric Differentiation of Al³⁺ and Zn²⁺ Using an AIE-Active Single Sensor

Solvent-Regulated Fluorimetric Differentiation of Al³⁺ and Zn²⁺ Using an AIE-Active Single Sensor

Luminescence and Electrochemical Activity of New Unsymmetrical 3-Imino-1,8-naphthalimide Derivatives

Acid selective pro-dye for cellular compartments

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Aggregation-Induced Emission or Hydrolysis by Water? The Case of Schiff Bases in Aqueous Organic Solvents

Cited by 46 publications

References 40 publications

Solvent-Regulated Fluorimetric Differentiation of Al3+ and Zn2+ Using an AIE-Active Single Sensor

Solvent-Regulated Fluorimetric Differentiation of Al3+ and Zn2+ Using an AIE-Active Single Sensor

Luminescence and Electrochemical Activity of New Unsymmetrical 3-Imino-1,8-naphthalimide Derivatives

Acid selective pro-dye for cellular compartments

Contact Info

Product

Resources

About

Solvent-Regulated Fluorimetric Differentiation of Al³⁺ and Zn²⁺ Using an AIE-Active Single Sensor

Solvent-Regulated Fluorimetric Differentiation of Al³⁺ and Zn²⁺ Using an AIE-Active Single Sensor