Investigation of the chemical and optical properties of halogen-substituted N-methyl-4-piperidone curcumin analogs by density functional theory calculations

Hutama, Aulia Sukma; Huang, Hendra; Kurniawan, Yehezkiel Steven

doi:10.1016/j.saa.2019.117152

Cited by 15 publications

(7 citation statements)

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“…From the optimized three-dimensional structure of biolubricant compounds, the bond length, bond angle, and dihedral angle of the heterocyclic and ester moieties were calculated and listed in Table S1. The bond length of C1-O21 is the shortest due to the double bond of the carbonyl compound, while the other bond lengths, bond angles, and dihedral angles are reasonable for single bond heterocyclic compounds [20].…”

Section: Resultsmentioning

confidence: 92%

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Computational and Experimental Studies of Biolubricant Stability Derived from Oleic Acid

2020

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In the present work, the stability of six biolubricant compounds, i.e. Acetal, Ketal, D[4.4], D[4.5], Cyclic-6, and Cyclic-7, was evaluated both theoretically and experimentally. These compounds were prepared from oleic acid through hydroxylation and esterification reactions. The computational study of the compounds was conducted by using the Density Functional Theory (DFT) method at B3LYP level of theory and 6-31 G (d,p) basis set. The theoretical stability was reflected from the internal energy value of the hydrolysis reaction of the biolubricant compounds to form the 9,10-dihydroxystearic acid. The order of stability is given as follows: Cyclic-6 (-3.458 kJ/mol) > Acetal (-3.446 kJ/mol) > Cyclic-7 (-3.364 kJ/mol) > D[4.5] (-3.343 kJ/mol) > D[4.4] (-3.261 kJ/mol) > Ketal (-3.058 kJ/mol). On the other hand, the experimental stability of the biolubricant compounds was measured using the American Society for Testing and Material (ASTM) standard method for total acid number (TAN) and total base number (TBN). It was found that the Cyclic-6 derivative yielded the lowest TAN (1.37 mg KOH/g) and TBN (3.53 mg KOH/g) values compared to the other biolubricant compounds. Meanwhile, the Cyclic-6 also showed the lowest internal energy value (-3.458 kJ/mol) from the computational study due to the high stability of six-membered ring. These results reveal that the experimental TAN and TBN values could be predicted from the theoretical internal energy value, i.e. TAN (mg KOH/g) = 35.183 (DE) – 123.02 (R2 = 0.9226) and TBN (mg KOH/g) = 105.71 (DE) – 369.72 (R2 = 0.8946), which is remarkable.

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Section: Resultsmentioning

confidence: 92%

“…and Cyclic-7). These biolubricant compounds were modeled using the DFT method with B3LYP hybrid functional and 6-31 G (d,p) as the basis set since it is suitable for the computational study of heterocyclic compounds [20]. The three-dimensional structure of the biolubricant compounds is shown in Figure 2.…”

Section: Resultsmentioning

confidence: 99%

Computational and Experimental Studies of Biolubricant Stability Derived from Oleic Acid

2020

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“…Literature had reported many studies that had accounted the enhanced NLO activity of molecules right after the substitution of halogens. The research work had been reported for the investigation of NLO activity of the p-idoaniline and p-bromoaniline [27], Schiff's base material: 4-chloro-4′bromobenzylidene aniline [28], N-methyl-4-piperiodones curcumin [29], chalcones [30], after the substitution of the halogens. Immense rise in the NLO activity of the molecules was seen in the mentioned studies that motivated us to proceed the present study.…”

Section: Introductionmentioning

confidence: 99%

Investigation of the electronic and optical activity of halogen-substituted 2-nitrotoulene by density functional theory

2023

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The enhancement of NLO activity of the 2-nitrotoulene (2NT) after the substitution of the halogens (F, Cl, Br and I) at the para position of the benzene ring was reported in the paper. All the computational details were mentioned using density functional theory with B3LYP/6-311G basis set. The engagement of the electrophilic and nucleophilic regions in molecules was established using counter plots. Mulliken charge analysis and frontier molecular orbital parameters laid the high chemical reactivity of 2NT molecule after the substitution of F, Cl, Br, and I. Electronic properties were analyzed by computing absorption and emission spectra using time-dependent density functional theory. The Higher Raman intensity modes and higher absorbance intensity curve for iodine substituted 2NT (2NT-I) highlighted the highest reactivity.The lowest band gap was reported for 2NT-I (4.03 eV) that better correlates with the charge and spectral ndings. The polarizability parameters set a fair comparison between the NLO activities of the molecules.2NT-I has the highest values of polarizability parameters among the other molecules.

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“…The DFT is used as it is widely known to be more powerful than some simple approximations, such as the semi-classical approximations and the simple matrix methods neglecting electron-electron correlation [46][47][48][49][50][51][52][53][54]. The DFT has been widely applied to various materials and has proven accurate [55][56][57][58][59][60][61][62][63][64].…”

Section: Introductionmentioning

confidence: 99%

Lead-free Perovskites TlGeCl_xBr_3-x (x=0,1,2,3) as Promising Materials for Solar Cell Application: a DFT Study

Pingak,

Johannes,

Hauwali

et al. 2023

J. Phys.: Conf. Ser.

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This study investigates the structural parameters and the electronic properties of cubic TlGeClxBr3-x (x=0,1,2,3) lead-free perovskites to evaluate their potential as absorbers in perovskite solar cell devices. Density Functional Theory (DFT) embedded in the Quantum Espresso code was used to calculate these properties. The results revealed that the compounds have optimized lattice constants of 5.244 Å, 5.336 Å, 5.416 Å, and 5.501 Å, for TlGeCl3, TlGeCl2Br, TlGeClBr2, and TlGeBr3 perovskites, respectively. In addition, the compounds are direct band gap (R→R) semiconductors with energy gap values of 0.847 eV, 0.683 eV, 0.556 eV, and 0.518 eV for the respective materials. It is important to note that the band gap of the perovskites reduces as a Cl− ion, two and three Cl− ions are replaced by a Br− ion, two and three Br− ions, respectively. The analysis of their projected density of states indicated that near the valence band maximum of the perovskites, Cl-3p and Br-4p states contributes the most to their total DOS. In contrast, the Ge-4p orbital is the most dominant state close to the conduction band minimum. Based on these energy gap values, the studied materials are promising candidates for lead-free perovskite solar cell devices, with TlGeBr3 projected to be more promising than the other three materials.

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Investigation of the chemical and optical properties of halogen-substituted N-methyl-4-piperidone curcumin analogs by density functional theory calculations

Cited by 15 publications

References 50 publications

Computational and Experimental Studies of Biolubricant Stability Derived from Oleic Acid

Computational and Experimental Studies of Biolubricant Stability Derived from Oleic Acid

Investigation of the electronic and optical activity of halogen-substituted 2-nitrotoulene by density functional theory

Lead-free Perovskites TlGeCl_xBr_3-x (x=0,1,2,3) as Promising Materials for Solar Cell Application: a DFT Study

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Investigation of the chemical and optical properties of halogen-substituted N-methyl-4-piperidone curcumin analogs by density functional theory calculations

Cited by 15 publications

References 50 publications

Computational and Experimental Studies of Biolubricant Stability Derived from Oleic Acid

Computational and Experimental Studies of Biolubricant Stability Derived from Oleic Acid

Investigation of the electronic and optical activity of halogen-substituted 2-nitrotoulene by density functional theory

Lead-free Perovskites TlGeClxBr3-x (x=0,1,2,3) as Promising Materials for Solar Cell Application: a DFT Study

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Lead-free Perovskites TlGeCl_xBr_3-x (x=0,1,2,3) as Promising Materials for Solar Cell Application: a DFT Study