Startseite Solvent effect, dipole moment, and DFT studies of multi donor–acceptor type pyridine derivative
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Solvent effect, dipole moment, and DFT studies of multi donor–acceptor type pyridine derivative

  • Saleh S. Alarfaji , Abdullah G. Al-Sehemi und Mehboobali Pannipara EMAIL logo
Veröffentlicht/Copyright: 7. Dezember 2022

Abstract

A donor–acceptor substituted derivative 2,6-diamino-4-(3,4,5-trimethoxy-phenyl)-pyridine-3,5-dicarbonitrile (DTPP) has been synthesized and its photophysical properties have been studied. Effect of solvent on the photophysical features of DTPP has been undertaken by steady state absorption and emission techniques. Strong solvatochromic emission has been observed due to intramolecular charge transfer characteristics, upon changing the solvent polarity, revealing the highly polar character of the excited state. Dipole moment changes between the excited and ground state have been estimated by using the theory of solvatochromism from Lippert–Mataga and Reichardt’s correlations. The geometrical parameters for ground and excited states, conformational flexibility, and NLO behavior of the molecule have been theoretically investigated. The electronic distributions of DTPP in HOMO and LUMO were also investigated using density functional theory (DFT) methods at B3LYP/6-31 G** level. The correlation of experimental results with theoretical predictions obtained via DFT substantiates the presence of polarity dependent of the emission spectra.

1 Introduction

Research on adaptable and responsive systems has endorsed considerable interest in recent years and has led to great effort in the chemistry of photochromic and thermochromic organic materials. Applications for photo-induced responsive organic luminescent dyes range from energy production, chemical sensing, molecular actuators, to biological systems [1,2,3,4,5]. To achieve long-lasting organic dyes with tunable electronic properties and variable efficiency of electron-hole combination, researchers have been examining multi donor–acceptor systems. Intramolecular charge transfer (ICT) [6] is a phenomenon that occurs when π-conjugated organic molecules with donor–acceptor groups and strong electron delocalized systems along their backbone are exposed to photon; consequently, the majority of research on this class of compounds focuses on how to inhibit or take advantage of the ICT effect. Furthermore, fluorophores bearing the ICT properties have been extensively utilized in the applications of bio-imaging and organic light-emitting diodes [7,8].

The degree of electronic distribution in a molecule can be determined by understanding the dipole moment. The redistribution of charges caused by photonic excitation of an electron in a molecule causes conformational changes in the excited state and modifies the dipole moment of the excited state (μ e) relative to the ground state (μ g). A molecule’s excited-state dipole moment is very helpful in revealing important information about its electronic and geometrical structures, which aids in understanding photophysical and photochemical processes. Understanding the excited state dipole moment is important for evaluating the effectiveness of quantum chemical wave function derivations and electron correlation treatments. This is especially true in respect to the design of organic compounds with substantial hyperpolarizabilities [9,10,11,12]. The present stratagem aims at prediction of photophysical parameters of a multi donor–acceptor type pyridine derivative having π-conjugated flat rigid planar structure by applying solvent shift method, and in order to compare the electrical configurations with experimental data, theoretical computations were performed.

2 Experimental

2.1 Procedure for the synthesis of DTPP

The desired compound was synthesized by reacting 3,4,5-trimethoxy benzaldehyde with malononitrile in the presence of ammonia (Scheme 1 and the detailed synthetic and experimental part is explained in Supplementary information).

Scheme 1 
                  Synthetic route of DTTP.
Scheme 1

Synthetic route of DTTP.

3 Results and discussion

3.1 Solvent effect on absorption and emission characteristics

The steady state absorption and emission spectra of the DTPP (∼10−5 M) are recorded in non-polar, polar aprotic, and polar protic solvents. Figures 1 and 2 depict the absorption and emission spectra recorded in some selective solvents and the detailed spectral data are summarized in Table 1. Barring toluene and acetonitrile, spectral absorption band maxima for all solvents lie within the range of 349–352 nm with broad spectrum that can be assigned to S0 → S1 transition and is indicative of its being a π–π* type transition [13]. Interestingly, the absorption spectra in toluene and acetonitrile undergo a red shift of ∼20 nm on increasing solvent polarity from toluene to alcoholic solvents and this kind of shift could be observed due to greater degree of stabilization of the ground state in non-polar environments [14,15].

Figure 1 
                  Electronic absorption spectra of 1 × 10−5 mol L−1 of DTTP in different solvents.
Figure 1

Electronic absorption spectra of 1 × 10−5 mol L−1 of DTTP in different solvents.

Figure 2 
                  Emission spectra of 1 × 10−5 mol L−1 of DTTP in different solvents (λ
                     ex = 365 nm).
Figure 2

Emission spectra of 1 × 10−5 mol L−1 of DTTP in different solvents (λ ex = 365 nm).

Table 1

Spectral and photophysical parameters of DTPP in different solvents

Solvents λ abs (nm) λ em (nm) Δ ν ¯ (cm−1) ε (M −1 cm)−1 Φ f f μ 12 Debye ET (30) kcal mol−1 Δf(D,n) E T N
Toluene 371 425 3,425 11,820 0.22 0.25 4.47 33.9 0.0132 0.099
Dioxane 351 433 5,395 18,310 0.28 0.40 5.48 36 0.021 0.164
THF 349 445 6,181 15,940 0.18 0.36 5.19 37.4 0.210 0.210
Acetonitrile 364 443 4,899 18,910 0.36 0.45 5.86 45.6 0.304 0.472
Chloroform 350 436 5,636 15,490 0.14 0.34 4.99 39.1 0.148 0.259
Dichloromethane 349 451 6,480 24,460 0.14 0.55 6.38 40.7 0.218 0.309
Propanol 350 488 8,080 14,030 0.18 0.32 4.87 49.2 0.274 0.570
Ethanol 351 456 6,560 22,950 0.13 0.51 6.16 51.9 0.288 0.654
Methanol 352 455 6,431 14,220 0.13 0.32 4.86 55.4 0.308 0.762

Solvent effect on the emission spectral characteristics demonstrates how the protic nature of the solvent and the various solvent polarity have varied effects on the fluorescence spectra. As inferred from Figure 2, on excitation at 365 nm, the emission spectrum undergoing a remarkable red shift of 63 nm is observed on going from toluene to propanol with a reduction in the emission intensity, demonstrating that photo-induced ICT from the electron-donating methoxy group to the electron-accepting pyridine ring, with a greater dipole moment in the excited state than in the ground state, is involved in the singlet excited state [16]. Furthermore, the size of the Stokes shift also suggests ICT, and significant Stokes shifts suggest that the fluorophores can adopt twisted ICT state in the solution. The later results conclude that solvent polarizability is the most significant contributor in the case of absorption. In contrast, solvent polarizability and solvent polarity are important in the case of fluorescence. Figure 3 shows the solvent polarity (Δf) dependent changes in the absorption and fluorescence peak energies in cm−1 and the ν ̅ abs and ν ̅ fl values follow reasonably good linear relationship with the solvent polarity parameter Δf, suggesting that the ground and excited state nature of DTPP dye involved in the absorption and fluorescence processes essentially remain unchanged in all the solvents studied [17,18]. The slight negative slopes suggest that both absorption and fluorescent states are strongly dipolar in nature due to strong ICT from the donor to the acceptor moieties of the dye.

Figure 3 
                  Plot of energy of absorption and emission (cm−1) vs Δf of different solvents.
Figure 3

Plot of energy of absorption and emission (cm−1) vs Δf of different solvents.

A comparison technique was used to evaluate the fluorescence quantum yield (ϕ f) (equation (S1)) values in various solvents and solvent mixtures, and the results are reported in Table 1. The polarity and hydrogen bonding capacity of the solvents have a significant impact on the fluorescence quantum yield of DTPP, with the latter showing a very rapid reduction with increasing solvent polarity. The decrease in ϕ f could be attributed to effective internal conversion by significant mixing between the closely spaced singlet states of π–π* and n–π* [19]. The efficiency decreases with the increase in the solvent polarity and strong hydrogen bonding characteristics, as shown in Table 1.

3.2 Estimation of dipole moment

Transitions between ground and excited electronic states cause the Stokes shift of molecules with absorption and fluorescence spectra and is expected to follow a linear relationship with solvent orientation polarizability (Δf), as given by Lippert–Mataga equation (equations (S2) and (S3)) [20,21] and can be used to determine difference in ground and excited state dipole moments.

Though there exist some solute–solvent hydrogen bonding interactions, the Δ ν ¯ (Stokes’ shift) values were seen to correlate reasonably well with ∆ƒ; the solvent orientation polarizability parameter [22,23] are as inferred from Table 1 and Figure 4. From the slope of the plot, the change in dipole moment is estimated to be 9.54 D suggesting strong ICT in the S1 state of the dye.

Figure 4 
                  Plot of ΔF vs Stokes shift (cm−1).
Figure 4

Plot of ΔF vs Stokes shift (cm−1).

Further, the above method is compared with spectral shift method, introduced by Reichardt [24], given by the equations (equations (S4)–(S7)), where the dipole moment changes are calculated by plotting the Stokes shift of the fluorophore to E T N (dimensionless microscopic solvent polarity parameter), as shown in Figure 5, and the value for Δμ is found to be 4.32 D.

Figure 5 
                  Plot of 
                        
                           
                           
                              
                                 
                                    E
                                 
                                 
                                    T
                                 
                                 
                                    N
                                 
                              
                           
                           {E}_{T}^{N}
                        
                      versus Stokes shift (cm−1).
Figure 5

Plot of E T N versus Stokes shift (cm−1).

The experimental oscillator strength values for DTPP in various solvents and transition dipole moment (μ 12) were calculated using equations (1) and (2) and the values of f and μ 12 are listed in Table 1 [25,26].

(1) μ 12 2 = f 4.72 × 10 7 E max ,

(2) f = 4.32 × 10 9 ε ( v ¯ ) d v ¯ ,

where, E max is the energy maximum absorption in cm−1, ν ¯ is the numerical value of the wave number measured in cm−1, and f is the oscillator strength which shows the active number of electrons whose transition from ground to excited state contributes to the absorption area of the electronic spectrum. The values of f and μ 12 are listed in Table 1.

4 Theoretical investigation

Computational studies were performed to evaluate the nature of electronic transitions in the molecules in ground and excited state. The geometry optimization of ground state (S0) equilibrium structure of DTPP was performed without symmetry constraints in the gas phase and in solution using density functional theory (DFT) and time dependent density functional theory, with Gaussian 16 package [27]. The ground state (S0) and excited state (S1) geometries have been computed at B3LYP/6-31G** level of theory in acetonitrile. The optimized geometrical parameters bond lengths (Å), bond angles, and dihedral angles (degrees) for ground and excited states are labelled and depicted in Figure 6 and selected bond angles and bond lengths are depicted in Table S1. The results revealed that bond length increased from ground state to excited state in C1–C2, C1–O1, C4–C5, C5–O3, C11–C10, C10–N1, C9–N1, and C9-N3 as 0.063, 0.011, 0.0046, 0.0154, 0.0086, 0.0294, 0.0294, and 0.0263 Å, respectively, while bond length shortened from ground state to excited state in, C2–C3, C3–C4, C7–C11, C7–C8, C8–C9, C8–C12, C12–N4, C11–C13, C13–N5, O1–C14, O2–C15, and O3–C16 as 0.0026, 0.0023, 0.0051, 0.0043, 0.0086, 0.0073, 0.0026, 0,007, 0.0026, 0.01, 0.0088, and 0.0082 Å, respectively.

Figure 6 
               Optimized geometry of DTPP in acetonitrile solvent in the ground and excited states.
Figure 6

Optimized geometry of DTPP in acetonitrile solvent in the ground and excited states.

4.1 Conformational analysis

In order to describe conformational flexibility of the title compound, the energy profile as a function of C4–C3–C7–C11 torsion angle was performed with B3LYP method using 6-31 G(d,p) basis set (Figure 7). Using the scan option, the dihedral angle C4–C3–C7–C11, is varied in steps of 10° for the angle −180 to +180° to get the stable geometry of the molecule. The four stable conformers A, B, C, and D are observed for the title compound molecule having energies 6.01, 0.033, 1.16, and 8.49 (kcal mol−1), respectively. The minimum energy is observed for the conformer B with stability of the conformers in the order D > A > C > B.

Figure 7 
                  Possible conformers of DTPP. (a) D = 0; 8.49, (b) D = 90; 1.16, (c) D = 130; 0.033, and (d) D = 170; 6.01.
Figure 7

Possible conformers of DTPP. (a) D = 0; 8.49, (b) D = 90; 1.16, (c) D = 130; 0.033, and (d) D = 170; 6.01.

4.2 Electronic properties

Figure 8 shows the electronic distributions of DTPP and the estimated pattern of the highest occupied (HOMO) and lowest unoccupied (LUMO) molecular orbitals. The oxygen atom has a single pair of electrons and a delocalized HOMO on its left side. The LUMO has an antibonding nature with π* and is dispersed across the entire system. The orbital energy level analysis at the B3LYP/6-31 G* level showed HOMO energy (E HOMO) and LUMO energy (E LUMO) and HOMO–LUMO energy gap (E gap) was found to be 4.5 eV which has been used as an indicator of kinetic stability of the molecule. Since adding electrons to a high-lying LUMO or removing electrons from a low-lying HOMO is energetically unfavorable, a big HOMO–LUMO gap predicts a high kinetic stability and low chemical reactivity.

Figure 8 
                  Representations of HOMO and LUMO orbital density of DTPP at B3LYP/6-31 G** level.
Figure 8

Representations of HOMO and LUMO orbital density of DTPP at B3LYP/6-31 G** level.

4.3 The molecular electrostatic potential (MESP)

The electronic density and the prevalence of either negative or positive charge contributions determine the MESP. Consequently, electrophilic and nucleophilic attack sites can be identified through examination of the MESP surface. The MESP map for title molecule, as shown in Figure 9, was calculated at the B3lyp/6-31 G** method which displays the reactivity according to the colors of the region for electrophilic attack and the regions for nucleophilic attack. The MESP measurements show that it is largely concentrated at the oxygen atoms within the molecule and is reflected as a yellowish lobe. Because MESP correlates with electronegativity and partial charges, this outcome is expected. Nucleophilic attack regions were associated with the negative (red) sections of MESP map, while nucleophilic reactivity was associated with the positive (blue) regions (electrophilic attack regions). The red region of greatest negative electrostatic potential illustrates the relationship between the high nucleophilic reactivity of the ligand and the high electronegativity of the OMe and CN groups.

Figure 9 
                  The MESP surfaces of the studied compounds.
Figure 9

The MESP surfaces of the studied compounds.

4.4 Non-linear optical properties

The first hyperpolarizabilities (β 0) of the studied compound have been calculated at B3LYP/6-31 G**, B3LYP/6-31+G**, and B3LYP/6-31++G** levels of theories. The β 0 is third rank tensor that can be described by 3 × 3 × 3 matrix. The 27 components of the 3D matrix can be reduced to 10 components due to the Kleinman symmetry [28]. The β 0 can be evaluated by using x, y, z components as

β 0 = ( β x + β y + β z ) 1 / 2 ,

where

β x = β x x x + β x y y + β x z z ,

β y = β y y y + β x x z + β y y z ,

β z = β z z z + β x x z + β y y z .

The calculated β 0 values at all the levels of theories have been presented in Table 2. The β 0 value of chloramphenicol at HF/6-31G* level of theory is half of that computed at DFT level of theory. The first hyperpolarizability (β) value was found to be 66.7 × 10−31 esu, which is 8.5 times greater than that of urea which indicates the molecule as NLO material (For urea β = 7.803 × 10−31 esu obtained by B3LYP/6-311++G(d,p) method. The hyperpolarizability dominated by the longitudinal components of β xxx = −1445.27, and the values are listed in Table 2.

Table 2

Calculated values of hyperpolarizability by DFT/B3LYP, using/6-31 G**, 6-31 + G**, and 6-31 + + G** basis set

B3LYP/6-31 G** B3LYP/6-31 + G** B3LYP/6-31 + + G**
β xxx −1283.4852435 −1462.696254 −1445.266541
β xxy 72.7121474 84.0963565 86.5045141
β xyy 564.112952 644.4584544 646.4512231
β yyy −0.8555952 22.3118324 16.6684937
β xxz 24.1235458 20.191913 24.089777
β xyz 217.602984 279.996269 275.78418
β yyz −10.7276545 -10.2439392 −8.8522702
β xzz 101.517455 34.8927433 37.4187882
β yzz 13.4112714 1.8494042 9.2512503
β zzz 27.8621646 49.8533089 52.3192204
β 0 × 10−30 esu 54.0 × 10−31 68.5 × 10−31 66.7 × 10−31

5 Conclusion

A multi donor–acceptor substituted pyridine derivative was developed, characterized, and its photophysical activity has been investigated both experimentally and theoretically using quantum chemical calculations. Different organic solvents with differing degrees of polarity are studied for their effects on the absorption and emission spectra. Due to ICT and intermolecular hydrogen bonding between the solute and solvent, the emission spectra of DTPP exhibits a red shift as the solvent polarity is increased. The change in dipole moments (Δμ) associated with the first excited singlet state is calculated by solvatochromic Stokes shift method from Lippert–Mataga and Reichardt equations. The higher value of (Δμ) suggests that the emissive state of DTPP is more polar than the ground state. The geometrical parameters, conformational flexibility, and NLO behavior of the molecule have been theoretically investigated. The electronic distributions of DTPP in HOMO and LUMO were also investigated using DFT method.


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  1. Funding information: The Deanship of Scientific Research at King Khalid University is greatly appreciated for funding this work under Grant number R.G.P.-2/179/43.

  2. Author contributions: Saleh S. Alarfaji: conceptualization, methodology, and investigation; AbdullahG. Al-Sehemi: formal analysis and conceptualization; Mehboobali Pannipara: conceptualization, supervision, writing – review & editing.

  3. Conflict of interest: The authors declare that there is no Conflict of interest.

  4. Ethical approval: The conducted research is not related to either human or animal use.

  5. Data availability statement: Data sharing is not applicable to this article as no datasets were generated or analyzed during the current study.

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Received: 2022-09-18
Revised: 2022-10-30
Accepted: 2022-11-02
Published Online: 2022-12-07

© 2022 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  39. Diagnostic and therapeutic radioisotopes in nuclear medicine: Determination of gamma-ray transmission factors and safety competencies of high-dense and transparent glassy shields
  40. Calculation of NaI(Tl) detector efficiency using 226Ra, 232Th, and 40K radioisotopes: Three-phase Monte Carlo simulation study
  41. Isolation and identification of unstable components from Caesalpinia sappan by high-speed counter-current chromatography combined with preparative high-performance liquid chromatography
  42. Quantification of biomarkers and evaluation of antioxidant, anti-inflammatory, and cytotoxicity properties of Dodonaea viscosa grown in Saudi Arabia using HPTLC technique
  43. Characterization of the elastic modulus of ceramic–metal composites with physical and mechanical properties by ultrasonic technique
  44. GC-MS analysis of Vespa velutina auraria Smith and its anti-inflammatory and antioxidant activities in vitro
  45. Texturing of nanocoatings for surface acoustic wave-based sensors for volatile organic compounds
  46. Insights into the molecular basis of some chalcone analogues as potential inhibitors of Leishmania donovani: An integrated in silico and in vitro study
  47. (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity
  48. On the relative extraction rates of colour compounds and caffeine during brewing, an investigation of tea over time and temperature
  49. Characterization of egg shell powder-doped ceramic–metal composites
  50. Rapeseed oil-based hippurate amide nanocomposite coating material for anticorrosive and antibacterial applications
  51. Chemically modified Teucrium polium (Lamiaceae) plant act as an effective adsorbent tool for potassium permanganate (KMnO4) in wastewater remediation
  52. Efficiency analysis of photovoltaic systems installed in different geographical locations
  53. Risk prioritization model driven by success factor in the light of multicriteria decision making
  54. Theoretical investigations on the excited-state intramolecular proton transfer in the solvated 2-hydroxy-1-naphthaldehyde carbohydrazone
  55. Mechanical and gamma-ray shielding examinations of Bi2O3–PbO–CdO–B2O3 glass system
  56. Machine learning-based forecasting of potability of drinking water through adaptive boosting model
  57. The potential effect of the Rumex vesicarius water seeds extract treatment on mice before and during pregnancy on the serum enzymes and the histology of kidney and liver
  58. Impact of benzimidazole functional groups on the n-doping properties of benzimidazole derivatives
  59. Extraction of red pigment from Chinese jujube peel and the antioxidant activity of the pigment extracts
  60. Flexural strength and thermal properties of carbon black nanoparticle reinforced epoxy composites obtained from waste tires
  61. A focusing study on radioprotective and antioxidant effects of Annona muricata leaf extract in the circulation and liver tissue: Clinical and experimental studies
  62. Clinical comprehensive and experimental assessment of the radioprotective effect of Annona muricata leaf extract to prevent cellular damage in the ileum tissue
  63. Effect of WC content on ultrasonic properties, thermal and electrical conductivity of WC–Co–Ni–Cr composites
  64. Influence of various class cleaning agents for prosthesis on Co–Cr alloy surface
  65. The synthesis of nanocellulose-based nanocomposites for the effective removal of hexavalent chromium ions from aqueous solution
  66. Study on the influence of physical interlayers on the remaining oil production under different development modes
  67. Optimized linear regression control of DC motor under various disturbances
  68. Influence of different sample preparation strategies on hypothesis-driven shotgun proteomic analysis of human saliva
  69. Determination of flow distance of the fluid metal due to fluidity in ductile iron casting by artificial neural networks approach
  70. Investigation of mechanical activation effect on high-volume natural pozzolanic cements
  71. In vitro: Anti-coccidia activity of Calotropis procera leaf extract on Eimeria papillata oocysts sporulation and sporozoite
  72. Determination of oil composition of cowpea (Vigna unguiculata L.) seeds under influence of organic fertilizer forms
  73. Activated partial thromboplastin time maybe associated with the prognosis of papillary thyroid carcinoma
  74. Treatment of rat brain ischemia model by NSCs-polymer scaffold transplantation
  75. Lead and cadmium removal with native yeast from coastal wetlands
  76. Characterization of electroless Ni-coated Fe–Co composite using powder metallurgy
  77. Ferrate synthesis using NaOCl and its application for dye removal
  78. Antioxidant, antidiabetic, and anticholinesterase potential of Chenopodium murale L. extracts using in vitro and in vivo approaches
  79. Study on essential oil, antioxidant activity, anti-human prostate cancer effects, and induction of apoptosis by Equisetum arvense
  80. Experimental study on turning machine with permanent magnetic cutting tool
  81. Numerical simulation and mathematical modeling of the casting process for pearlitic spheroidal graphite cast iron
  82. Design, synthesis, and cytotoxicity evaluation of novel thiophene, pyrimidine, pyridazine, and pyridine: Griseofulvin heterocyclic extension derivatives
  83. Isolation and identification of promising antibiotic-producing bacteria
  84. Ultrasonic-induced reversible blood–brain barrier opening: Safety evaluation into the cellular level
  85. Evaluation of phytochemical and antioxidant potential of various extracts from traditionally used medicinal plants of Pakistan
  86. Effect of calcium lactate in standard diet on selected markers of oxidative stress and inflammation in ovariectomized rats
  87. Identification of crucial salivary proteins/genes and pathways involved in pathogenesis of temporomandibular disorders
  88. Zirconium-modified attapulgite was used for removing of Cr(vi) in aqueous solution
  89. The stress distribution of different types of restorative materials in primary molar
  90. Reducing surface heat loss in steam boilers
  91. Deformation behavior and formability of friction stir processed DP600 steel
  92. Synthesis and characterization of bismuth oxide/commercial activated carbon composite for battery anode
  93. Phytochemical analysis of Ziziphus jujube leaf at different foliar ages based on widely targeted metabolomics
  94. Effects of in ovo injection of black cumin (Nigella sativa) extract on hatching performance of broiler eggs
  95. Separation and evaluation of potential antioxidant, analgesic, and anti-inflammatory activities of limonene-rich essential oils from Citrus sinensis (L.)
  96. Bioactivity of a polyhydroxy gorgostane steroid from Xenia umbellata
  97. BiCAM-based automated scoring system for digital logic circuit diagrams
  98. Analysis of standard systems with solar monitoring systems
  99. Structural and spectroscopic properties of voriconazole and fluconazole – Experimental and theoretical studies
  100. New plant resistance inducers based on polyamines
  101. Experimental investigation of single-lap bolted and bolted/bonded (hybrid) joints of polymeric plates
  102. Investigation of inlet air pressure and evaporative cooling of four different cogeneration cycles
  103. Review Articles
  104. Comprehensive review on synthesis, physicochemical properties, and application of activated carbon from the Arecaceae plants for enhanced wastewater treatment
  105. Research progress on speciation analysis of arsenic in traditional Chinese medicine
  106. Recent modified air-assisted liquid–liquid microextraction applications for medicines and organic compounds in various samples: A review
  107. An insight on Vietnamese bio-waste materials as activated carbon precursors for multiple applications in environmental protection
  108. Antimicrobial activities of the extracts and secondary metabolites from Clausena genus – A review
  109. Bioremediation of organic/heavy metal contaminants by mixed cultures of microorganisms: A review
  110. Sonodynamic therapy for breast cancer: A literature review
  111. Recent progress of amino acid transporters as a novel antitumor target
  112. Aconitum coreanum Rapaics: Botany, traditional uses, phytochemistry, pharmacology, and toxicology
  113. Corrigendum
  114. Corrigendum to “Petrology and geochemistry of multiphase post-granitic dikes: A case study from the Gabal Serbal area, Southwestern Sinai, Egypt”
  115. Corrigendum to “Design of a Robust sliding mode controller for bioreactor cultures in overflow metabolism via an interdisciplinary approach”
  116. Corrigendum to “Statistical analysis on the radiological assessment and geochemical studies of granite rocks in the north of Um Taghir area, Eastern Desert, Egypt”
  117. Corrigendum to “Aroma components of tobacco powder from different producing areas based on gas chromatography ion mobility spectrometry”
  118. Corrigendum to “Mechanical properties, elastic moduli, transmission factors, and gamma-ray-shielding performances of Bi2O3–P2O5–B2O3–V2O5 quaternary glass system”
  119. Erratum
  120. Erratum to “Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies”
  121. Special Issue on Applied Biochemistry and Biotechnology (ABB 2021)
  122. Study of solidification and stabilization of heavy metals by passivators in heavy metal-contaminated soil
  123. Human health risk assessment and distribution of VOCs in a chemical site, Weinan, China
  124. Preparation and characterization of Sparassis latifolia β-glucan microcapsules
  125. Special Issue on the Conference of Energy, Fuels, Environment 2020
  126. Improving the thermal performance of existing buildings in light of the requirements of the EU directive 2010/31/EU in Poland
  127. Special Issue on Ethnobotanical, Phytochemical and Biological Investigation of Medicinal Plants
  128. Study of plant resources with ethnomedicinal relevance from district Bagh, Azad Jammu and Kashmir, Pakistan
  129. Studies on the chemical composition of plants used in traditional medicine in Congo
  130. Special Issue on Applied Chemistry in Agriculture and Food Science
  131. Strip spraying technology for precise herbicide application in carrot fields
  132. Special Issue on Pharmacology and Metabolomics of Ethnobotanical and Herbal Medicine
  133. Phytochemical profiling, antibacterial and antioxidant properties of Crocus sativus flower: A comparison between tepals and stigmas
  134. Antioxidant and antimicrobial properties of polyphenolics from Withania adpressa (Coss.) Batt. against selected drug-resistant bacterial strains
  135. Integrating network pharmacology and molecular docking to explore the potential mechanism of Xinguan No. 3 in the treatment of COVID-19
  136. Chemical composition and in vitro and in vivo biological assortment of fixed oil extracted from Ficus benghalensis L.
  137. A review of the pharmacological activities and protective effects of Inonotus obliquus triterpenoids in kidney diseases
  138. Ethnopharmacological study of medicinal plants in Kastamonu province (Türkiye)
  139. Protective effects of asperuloside against cyclophosphamide-induced urotoxicity and hematotoxicity in rats
  140. Special Issue on Essential Oil, Extraction, Phytochemistry, Advances, and Application
  141. Identification of volatile compounds and antioxidant, antibacterial, and antifungal properties against drug-resistant microbes of essential oils from the leaves of Mentha rotundifolia var. apodysa Briq. (Lamiaceae)
  142. Phenolic contents, anticancer, antioxidant, and antimicrobial capacities of MeOH extract from the aerial parts of Trema orientalis plant
  143. Chemical composition and antimicrobial activity of essential oils from Mentha pulegium and Rosmarinus officinalis against multidrug-resistant microbes and their acute toxicity study
  144. Special Issue on Marine Environmental Sciences and Significance of the Multidisciplinary Approaches
  145. An insightful overview of the distribution pattern of polycyclic aromatic hydrocarbon in the marine sediments of the Red Sea
  146. Antifungal–antiproliferative norcycloartane-type triterpenes from the Red Sea green alga Tydemania expeditionis
  147. Solvent effect, dipole moment, and DFT studies of multi donor–acceptor type pyridine derivative
  148. An extensive assessment on the distribution pattern of organic contaminants in the aerosols samples in the Middle East
  149. Special Issue on 4th IC3PE
  150. Energetics of carboxylic acid–pyridine heterosynthon revisited: A computational study of intermolecular hydrogen bond domination on phenylacetic acid–nicotinamide cocrystals
  151. A review: Silver–zinc oxide nanoparticles – organoclay-reinforced chitosan bionanocomposites for food packaging
  152. Green synthesis of magnetic activated carbon from peanut shells functionalized with TiO2 photocatalyst for Batik liquid waste treatment
  153. Coagulation activity of liquid extraction of Leucaena leucocephala and Sesbania grandiflora on the removal of turbidity
  154. Hydrocracking optimization of palm oil over NiMoO4/activated carbon catalyst to produce biogasoline and kerosine
  155. Special Issue on Pharmacology and metabolomics of ethnobotanical and herbal medicine
  156. Cynarin inhibits PDGF-BB-induced proliferation and activation in hepatic stellate cells through PPARγ
  157. Special Issue on The 1st Malaysia International Conference on Nanotechnology & Catalysis (MICNC2021)
  158. Surfactant evaluation for enhanced oil recovery: Phase behavior and interfacial tension
  159. Topical Issue on phytochemicals, biological and toxicological analysis of aromatic medicinal plants
  160. Phytochemical analysis of leaves and stems of Physalis alkekengi L. (Solanaceae)
  161. Phytochemical and pharmacological profiling of Trewia nudiflora Linn. leaf extract deciphers therapeutic potentials against thrombosis, arthritis, helminths, and insects
  162. Pergularia tomentosa coupled with selenium nanoparticles salvaged lead acetate-induced redox imbalance, inflammation, apoptosis, and disruption of neurotransmission in rats’ brain
  163. Protective effect of Allium atroviolaceum-synthesized SeNPs on aluminum-induced brain damage in mice
  164. Mechanism study of Cordyceps sinensis alleviates renal ischemia–reperfusion injury
  165. Plant-derived bisbenzylisoquinoline alkaloid tetrandrine prevents human podocyte injury by regulating the miR-150-5p/NPHS1 axis
  166. Network pharmacology combined with molecular docking to explore the anti-osteoporosis mechanisms of β-ecdysone derived from medicinal plants
  167. Chinese medicinal plant Polygonum cuspidatum ameliorates silicosis via suppressing the Wnt/β-catenin pathway
  168. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part I
  169. Investigation of improved optical and conductivity properties of poly(methyl methacrylate)–MXenes (PMMA–MXenes) nanocomposite thin films for optoelectronic applications
  170. Special Issue on Applied Biochemistry and Biotechnology (ABB 2022)
  171. Model predictive control for precision irrigation of a Quinoa crop
Heruntergeladen am 13.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2022-0248/html
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