A Review on Pyrazolines as Colorimetric Fluorescent Chemosensors for Cu2.

The Pyrazoline derivatives display promising potential as sensitive and selective chemosensors for detecting Cu2+ ions. It has undergone screening for its sensing behavior with various metals using absorption, emission spectroscopic techniques. Their unique structure incorporates both donating and accepting sites, characterized by delocalized orbitals. These derivatives exhibit notable chromogenic and fluorogenic capabilities facilitated by intramolecular charge transfer. The sensors based on pyrazoline demonstrate exceptional selectivity, low detection limits, and precise detection of metal ions, particularly Cu2+. This review offers a comprehensive summary of recent discoveries concerning as pyrazoline-based "On-Off" chemosensors. The discussion places emphasis on exploring the design and photophysical properties of these chemosensors, with the primary objective of detecting Cu2+ metal ions. The unique features of pyrazoline derivatives make them promising candidates for practical applications in environmental and biological monitoring, showcasing their potential significance in advancing sensing technologies.

Synthesis of Fluorescent Pyrazoline Sensors as Versatile Tool for Zinc ion Detection: A Mini-Review.

Zinc ions are one of the 2nd most abundant mineral after iron and it is important for immune system, enzymatic catalysis, DNA synthesis, and maintaining structural integrity in humans. But, monitoring the Zn levels in human body poses more challenges. This review paper investigates (paper from 2010 to 2023) the synthesis of pyrazoline derivatives by different methods, including conventional methods and green chemistry protocol. These Pyrazoline derivatives highlighted for their potential application as chemo-sensor for Zn2+ ions recognition. Pyrazoline compounds exhibit excellent sensitivity & selectivity and emitting blue-light with high quantum yields and electroluminescence, along with a superior limit of detection. These derivatives are stable bioactive molecule, with well-known diverse biological activities. This review not only gives valuable insights into the essential role of Zinc in human physiology but also provides a practical method for accurate Zinc detection in various samples. Which holds the potential for advancements in health diagnostics and environmental monitoring. Because of their significant biological application and selectivity as sensors, researchers have much more attention to prepare green environmentally-friendly pyrazoline derivatives.

Synthesis, Physicochemical and Third Order Nonlinear Optical Properties of Bis-Chalcone (BBDP) as Donor-pi Acceptor Chromophore in Organize Medium.

Bis-Chalcone (BBDP) has been prepared by condensation of N, N-dimethyl benzaldehyde and 1,1'-([1,1'-biphenyl]-4,4'-diyl) di (ethan-1-one), and structure of BBDP was characterized by Mass Spectra, 13C-NMR, 1H-NMR, and IR. Physicochemical properties including Dipole-moments, Stoke-Shifts, Oscillator-strength, dielectric constant and quantum-yields of fluorescence of BBDP were investigated by the emission and absorbances in different solvents. Compound (BBDP) displayed bathochromic shift upon increasing the solvent polarity (from n-Hexane to DMSO). Furthermore, we have exploited third-order nonlinear optical characteristics of the bisChalone were invigilated by the Z-scan techniques in Chloroform. The measurements were taken with a continuous-wave (CW) diode laser having a wavelength of 520 nm in CHCl3 solvent. The third-order nonlinear optical properties, such as the nonlinear refractive index (NLRI) n2, nonlinear absorption coefficient (NLAC) ß, and nonlinear susceptibility χ(3), were measured at various solution concentrations and laser powers. The obtained values of n2, ß, and χ(3) were estimated to be high, of the order of 10-7(cm2/W), 10-3 (cm/W), and 10-6 (esu), respectively. As a result, bis-chalcone (BBDP) is considered as a promising candidate for applications in nonlinear optical (NLO) devices and optical limiting (OL).

Photophysical Investigation of One Pot Synthesized Novel Indenofluorene Derivative (BDP) as a Fluorescent Chemosensor for the Detection of Fe3+ Ion.

An Indane-1-one derivative 11-(1-benzyl-1H-indol-3-yl)-10,12-dihydrodiindeno[1,2-b:2',1'-e]-pyridine (BDP) has been synthesized by the reaction of Indan-1-one with 1-benzyl-1H-indole-3-carbaldehyde. FT-IR, 1H-NMR, 13N-NMR and Mass spectroscopic techniques has been used to confirmed the structure of BDP. The observed photophysical changes in BDP across various solvents were associated. The impact of various interactions on photophysical parameters, including Stokes shift, dipole moment, oscillator strength, and fluorescence quantum yields, has been assessed in relation to solvent polarity. Moreover, BDP demonstrates potential as a selective fluorescent chemosensor for detecting Fe3+ ion within a range of cations in an aqueous DMSO environment. A thorough investigation into the recognition mechanism of BDP towards Fe3+ ion has been conducted using Benesi-Hildebrand and Stern-Volmer, measurements. BDP forms a 2:1 complex with the Fe3+ ion, exhibiting fluorescent quenching behaviour.

Ultrasound-Assisted Synthesis of Chalcone: A Highly Sensitive and Selective Fluorescent Chemosensor for the Detection of Fe3+ in Aqueous Media.

The chalcone compound DHPO was synthesized through a chemical reaction between 1-(2-hydroxyphenyl)-ethanone and 3,4-dimethoxy benzaldehyde under ultrasound irradiation. The interaction between the DHPO compound and several metal ions was studied using fluorescence behavior, revealing that the chalcone function as a "turn on and turn off" switch fluorescent sensor, for selectively and sensitively detecting Fe3+ ions. The process of fluorescence quenching and complexation of DHPO with Fe3+ ion was further studied using methods such as Benesi-Hildebrand, Stern-Volmer plot, and job plot.

A Review on Schiff Base as a Versatile Fluorescent Chemo-sensors Tool for Detection of Cu2+ and Fe3+ Metal Ion.

Schiff bases as fluorescent Chemo-sensors fluorogenic cation sensors is scientifically exigent work. Recently Schiff bases derivatives gained more attention because of their structural variability. Donor and acceptor group joint with delocalized [Formula: see text]-orbital display excellent fluorescent properties due to intramolecular charge transfer (ICT). Schiff bases coordinate with the metal ions resulting in a small change of photophysical properties and typical sensing behavior hypochromic/hyperchromic or hypsochromic/bathochromic shift. In this review, we endeavored to converge the beforehand reported Schiff baes-derived sensors and investigated the probes' design, synthesis, ON/OFF & OFF/ON Fe 3+ and Cu2+ metal ion sensing mechanism, and practical application. This review focuses on the synthesis of Schiff baes as fluorescent Chemosensor for investigation of Fe and Cu metal ions during the period of over the two past decade (2003-2022). We anticipate that this review will provide a fundamental framework for researchers to further investigate the topic of Schiff-based sensors for metal ion detection.

Multi-step Synthesis, Characterization and Photophysical Investigation of Novel Biologically Active Heterocyclic Chalcone (AECO).

Novel alkylated heterocyclic chalcone (E)-1-(2-(allyloxy)phenyl)-3-(9-ethyl-9H-carbazol-3-yl)prop-2-en-1-one (AECO) with extended π-bond was prepared by the multi-steps synthesis. The structure of the AECO was established by the spectroscopic technics and purity of the compound was confirmed by the elemental analysis. Physicochemical parameters of the AECO such as molar absorption coefficient, transition dipole moments, stokes shift, oscillator strength and fluorescence quantum yield were calculated in ten various solvents on the basis of polarity of the solvents to see the effect of the solvent with AECO. Interaction of the AECO chromophore with cationic CTAB and anionic SDS surfactants were determined by using the fluorescence spectroscopy techniques. The intensity of the florescence spectrum increase with increasing the concentrations of surfactants. This suggests that strong interaction occurs between AECO with surfactants and this interaction arise from electrostatic forces. So, AECO chromophore could be used as analysis to define the Critical Micelle Concentration (CMC) of the surfactants. In addition the in-vitro antibacterial active of novel heterocyclic chalcone agents four bacteria's strain were evaluated and result showed AECO is beater antibacterial agent against Gram-Negative Bacteria (E. coli and S. flexneri) as compare to the Gram Negative Bacteria with respected to the standard drug Tetracycline.

Microwave assisted one-pot synthesis, photophysical and physicochemical studies of novel biologically active heterocyclic Donor (D)-π-Acceptor (A) chromophore.

A donor-π-acceptor (D-π-A) chromophore, 2-amino-4-(9-ethyl-9H-carbazol-3-yl)-8-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (AEDQ) was synthesized from the condensation of 6-methoxy-3,4-dihydronaphthalen-1(2H)-one, 9-ethyl-9H-carbazole-3-carbaldehyde, malononitrile and NH4OAc in ethanol. Spectroscopic techniques and elemental analysis were employed to establish the structure of AEDQ. Photophysical parameters and fluorescence quantum yield were calculated in the different polarity solvents to evaluate the interactions of the solvent with AEDQ chromophore. Further, the interaction of the AEDQ with cationic and anionic surfactants (CTAB, SDS) were also evaluated by using fluorescence spectroscopy techniques. The intensity of the fluorescence spectrum increased as the concentration of surfactants increased, suggesting that strong interaction occurs between AEDQ with surfactants, and this interaction arises from electrostatic forces. As a result, the AEDQ chromophore could be used to determine the CMC of surfactants. The disc diffusion and minimal inhibitory concentration (MIC) technique were used to test in-vitro antibacterial activity against Gram +ve and Gram -ve bacteria, and the results are compared with the standard drug, tetracycline. AEDQ also showed good ADMET, pharmacokinetics and drug-likeness properties, which are desirable for a good drug candidate. The molecule also fits well in the DNA gyrase A active pocket site with the binding free energy of -17.92 kcal/mol, which testifies its good antibacterial activity.

Synthesis of Nitrogen Containing Chalcone: A Highly Sensitive and Selective Fluorescent Chemosensor for the Fe3+ Metal Ion in Aqueous Media.

Title compound (PTPO) was synthesized by the reaction of 2-acetyl pyridine with 3,4,5-trimethoxy benzaldehyde. The structure of the compound has been confirmed by spectroscopic techniques. Interaction of chalcone with different metal cations was analyzed based on the fluorescence behavior. Results show that chalcone act as on-off switching fluorescent chemosensor for selective and sensitive detection iron metal ion. Mechanism of quenching and complexation were resolute by Benesi-Hildebrand, Stern-Volmer plot and Job-plot.

N-Trifluoroacetylated pyrazolines: Synthesis, characterization and antimicrobial studies.

A series of N-trifluoroacetyl-2-pyrazolines have been synthesized via cyclization of chalcones in the presence of trifluoroacetic acid and hydrazine as a base. The method used for the preparation of pyrazolines was found to be an efficient one as all of the compounds were obtained in good yield (up to 79%). Various spectroscopic techniques established the structures and additionally corroborated the compounds 2a and 2e by single crystal X-ray. Newly synthesized pyrazolines were investigated for their potential as antimicrobial agents. Compound 2a displayed promising antimicrobial activity against pathogenic Escherichia coli and Pseudomonas aeruginosa. Furthermore, the mechanism of the antimicrobial activity of 2a was demonstrated with the help of scanning electron microscopy (SEM), which revealed complete damage of the bacterial cell membrane, providing dead cell debris in the milieu. The minimum inhibitory concentration (MIC) observed was 79 and 90 µM against E. coli and P. aeruginosa, respectively. Hence, these compounds might be significantly useful in antimicrobial drug development.

How fluxional reactants limit the accuracy/efficiency of infrequent metadynamics.

In an infrequent metadynamics (iMetaD) simulation, a well-tempered metadynamics bias accumulates in the reactant basin, accelerating escapes to the product state. Like the earlier hyperdynamics strategy, iMetaD enables estimates of the unbiased escape rates. However, iMetaD applies the bias to visited locations in a collective variable (CV) space, not to the more specific visited locations in a full configuration space as done in hyperdynamics. This difference makes rate estimates from iMetaD sensitive to the choice of CVs, to parameters that control the bias deposition rate, and to the preparation of the initial state within the reactant basin. This paper uses an extremely simple discrete state model to illustrate complications that can arise in systems that exhibit fluxional transitions between sub-basins of the reactant state. Specifically, we show how the reactant-to-product escape time and relaxation times within the reactant basin(s) impose bounds on the admissible parameter choices for an iMetaD calculation. Predictions from the discrete state model are validated by iMetaD simulations on a corresponding two-dimensional potential energy surface.

Importance learning estimator for the site-averaged turnover frequency of a disordered solid catalyst.

For disordered catalysts such as atomically dispersed "single-atom" metals on amorphous silica, the active sites inherit different properties from their quenched-disordered local environments. The observed kinetics are site-averages, typically dominated by a small fraction of highly active sites. Standard sampling methods require expensive ab initio calculations at an intractable number of sites to converge on the site-averaged kinetics. We present a new method that efficiently estimates the site-averaged turnover frequency (TOF). The new estimator uses the same importance learning algorithm [Vandervelden et al., React. Chem. Eng. 5, 77 (2020)] that we previously used to compute the site-averaged activation energy. We demonstrate the method by computing the site-averaged TOF for a simple disordered lattice model of an amorphous catalyst. The results show that with the importance learning algorithm, the site-averaged TOF and activation energy can now be obtained concurrently with orders of magnitude reduction in required ab initio calculations.

Synthesis and evaluation of Quinoline-3-carbonitrile derivatives as potential antibacterial agents.

New quinoline-3-carbonitrile derivatives were synthesized and evaluated for their potential antibacterial behavior. Compounds were obtained by a one-pot multicomponent reaction of appropriate aldehyde, ethyl cyanoacetate, 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one and ammonium acetate. Structures were established by different physical and spectroscopic techniques. The molecular geometry, vibration frequencies, HOMO-LUMO energy gap, molecular hardness (g), ionization energy (IE), electron affinity (EA), and total energy of these compounds was assessed by DFT studies, employing DFT/RB3LYP method. Preliminary antibacterial studies using both Gram-positive and Gram-negative bacterial strains and cytotoxicity studies on mammalian cells revealed their promising antibacterial activity, without causing any severe host toxicity. All the compounds (QD1-QD5) in this study obeyed the 'Lipinski's Rule of Five' with logP values <5 and HBA <10, hydrogen bond donor's <5. The most active compound QD4 showed good interaction with the target DNA gyrase; target enzyme for quinoline class of antibiotics, which reveals its probable mechanism of action. Results of all these studies establish these compounds as important scaffolds with broad-spectrum antibacterial activity with no off-target toxicity. Having lower band gap energy of 3.40 eV and a low lying LUMO for compound QD4, this compound may be a valuable starting point for the development of quinoline-3-carbonitrile based broad-spectrum antibacterial agents.

Green Synthesis, Spectrofluorometric Characterization and Antibacterial Activity of Heterocyclic Compound from Chalcone on the Basis of in Vitro and Quantum Chemistry Calculation.

2-amino-4-(4-bromophenyl)-8-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (ABDC) was synthesized by the reaction of (2E)-2-(4 bromobenzylidene) - 6 -methoxy-3,4-dihydronaphthalen-1(2H)-one (Chalcone) with malononitrile and ammonium acetate under microwave irradiation. Chalcone was synthesised by the reaction 4-bromobenzaldehyd, 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one under the same condition. Structure of ABDC was conformed by 1H and 13C NMR, FT-IR, EI-MS spectral studies and elemental analysis. The electronic absorption and fluorescence spectra of ABDC have been studied in solvents of different polarities, and the data were used to study the solvatochromic properties such as excitation coefficient, stokes shift, oscillator strength, transition dipole moment and fluorescence quantum yield. The absorption maximum and fluorescence emission maximum was observed red shift when increase solvent polarity n-Hexane to DMSO. ABDC undergoes solubilization in different micelles and may be used as a probe and quencher to determine the critical micelle concentration (CMC) of CTAB and SDS. The anti-bacterial activity of chalcone and its cyclized product ABDC was tested in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria was determined with the reference of standard drug Tetracycline. Results showed that the ABDC is better anti-bacterial agent as compared to chalcone. The anti-bacterial activity was further supported by the quantum chemistry calculation.

Optical and Photophysical Investigation of (2E)-1-(2,5-Dimethylfuran-3-Yl)-3-(9-Ethyl-9H-Carbazol-3-Yl)Prop-2-en-1-One (DEPO) by Spectrofluorometer in Organized Medium.

(2E)-1-(2,5-dimethylfuran-3-yl)-3-(9-ethyl-9H-carbazol-3-yl)prop-2-en-1-one (DEPO) was prepared by the reaction of 9-ethyl-9H-carbazole-3-carbaldehyde with 1-(2,5-dimethylfuran-3-yl)ethanone under microwave irradiation. The structure of DEPO was established experimentally by EI-MS, FT-IR, 1H and 13C NMR spectral studies. Electronic absorption and emission spectra of DEPO were studied in different solvents on the basis of polarities, and the obtain data were used to determine the solvatochromic properties such as extinction coefficient, oscillator strength, transition dipole moment, stokes shift, fluorescence quantum yield and photochemical quantum yield. Photochemical quantum yield (Φ c ) of DEPO dye was determined in different solvent. The dye comparatively photostable in DMSO but undergoes photodecomposition in chloro methane solvents. The DEPO dye may be use as probe or quencher to determine critical micelle concentration (CMC) of cetyltri methyl ammonium bromide (CTAB) and sodium dodecyl sulfate (SDS).

Microwave Assisted Synthesis, Optical Properties and Physicochemical Investigations on the Powerful Fluorophore: Donor (D) -π-Acceptor (A) Chalcone.

(2E)-3-[4-(dimethylamino)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one (DPHP) was synthesized by the reaction 4(dimethylamino) benzaldehyde with 1-(2-hydroxyphenyl) ethanone under microwave irradiation. Structure of DPHP was conformed by 1H and 13C NMR, FT-IR, EI-MS spectral studies and elemental analysis. The electronic absorption and fluorescence spectra of DPHP have been studied in solvents of different polarities, and the data were used to study the solvatochromic properties such as extinction coefficient, stokes shift, oscillator strength, transition dipole moment, fluorescence quantum yield and photochemical quantum yield. The absorption maximum and fluorescence emission maximum was observed red shift when increase solvent polarity n-Hexane to DMF. DPHP undergoes solubilization in different micelles and may be used as a probe and quencher to determine the critical micelle concentration (CMC) of CTAB and SDS.

Microwave Assisted Synthesis, Spectrofluorometric Characterization of Azomethine as Intermediate for Transition Metal Complexes with Biological Application.

Azomethine (1, 5 - Dimethyl - 2 - phenyl -[(3, 4, 5 -trimethoxybenzylidene) amino] -1, 2 - dihydropyrazol - 3 - one) (DTAD) was synthesized by the reaction of 4-aminophenazone with 3,4,5 trimrthoxybenzaldehyd by microwave irradiation. Physicochemical studies such as electronic absorption, molar absorptivity, oscillator strength, dipole moment, florescent quantum yield were investigated in order to explore the analytical potential of azomethine dye. Azomethine go through the solubilization in different micelles and may be used as a probe or quencher to determine the critical micelle concentration (CMC) of SDS and CTAB. It's coordinate to metal salt through the pyrazol-3-one oxygen and the azomethine nitrogen. The structure of ligand and its meal complexes was elucidated by IR, (1)H, (13)C-NMR, EI-MS spectroscopic methods and elemental analysis. The antibacterial activity of these compounds were first tested in vitro by the disc diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration was using chloramphenicol as reference drug. The results showed that compound 1.1 is better inhibitor of both types of tested bacteria as compared to chloramphenicol.

Synthesis, Spectrofluorometric Studies, Micellization and non Linear Optical Properties of Blue Emitting Quinoline (AMQC) Dye.

Blue emitting 2-amino-4-(3, 4, 5-tri methoxyphenyl)-9-methoxy-5,6 dihydrobenzo[f]isoquinoline-1-carbonitrile (AMQC) dye was synthesized by one-pot multicomponent reactions (MCRs) of 3,4,5-trimethoxybenzaldehyd, malononitrile, 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one and ammonium acetate. Results obtained from spectroscopic and elemental analysis of synthesized AMQC was in good agreement with their chemical structures. Fluorescence polarity study demonstrated that AMQC was sensitive to the polarity of the microenvironment provided by different solvents. In addition, spectroscopic and physicochemical parameters, including electronic absorption, excitation coefficient, stokes shift, oscillator strength, transition dipole moment and fluorescence quantum yield were investigated in order to explore the analytical potential of AMQC. Dye undergoes solubilization in different micelles and may be used as a quencher and a probe to determine the critical micelle concentration (CMC) of SDS and CTAB. Nonlinear optical parameters of AMQC dye shows relatively lower nonlinear refractive index and nonlinear absorption coefficient at the power levels. Variation of n2 with concentration is linear in the concentration range used in the present study.

Physicochemical Investigation of 2,4,5-Trimethoxybenzylidene Propanedinitrile (TMPN) Dye as Fluorescence off-on Probe for Critical Micelle Concentration (CMC) of SDS and CTAB.

2,4,5-trimethoxybenzylidene propanedinitrile (TMPN) was synthesized by Knoevenagel condensation. Structure of the TMPN was conformed by the elemental analysis and EI-MS, FT-IR, (1)H-NMR, (13)C-NMR spectroscopy. Absorbance and emission spectrum of the TMPN was studied in different solvent provide that TMPN is good absorbent and emission red shift in absorbance and emission spectra as polarity of the solvents increase. Photophysical properties including, oscillator strength, extinction coefficient, transition dipole moment, stokes shift and fluorescence quantum yield were investigated in order to investigate the physicochemical behaviors of TMPN. Dye undergoes solubilization in different micelles and may be used as a probe to determine the critical micelle concentration (CMC) of SDS and CTAB.