Solubility behavior investigation of 1,4-cyclohexanedione in ten pure organic solvents by solubility measurement, correlation, DFT calculation and thermodynamic analysis

Li, Fanfan; Li, Yanxun; Wan, Yameng; Lv, Hanyu; Xu, Chenyang; Gao, Xuejin; Yu, Young Moon

doi:10.1016/j.jct.2023.107064

Cited by 10 publications

(6 citation statements)

References 49 publications

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“…Especially, the hydrogens of the phenyl ring and the methoxy group in 2MA tend to interact with the oxygen atoms of carbonyl units in A-EDOT molecules, and the formation of hydrogen bonds stabilizes their interaction energy. 46 Due to the intrinsic high polarity of the 2MA, the calculated absorption energy (E abs ) between A-EDOT and 2MA is −0.308 eV, greater than that of the combination of A-EDOT and CB (−0.057 eV). In the dissolution process, the greater E abs is more likely to force the solute to enter the hole in the solvent due to the generated intermolecular force.…”

Section: ■ Results and Discussionmentioning

confidence: 96%

“…As shown in Figure d,e and Table S2, the two solvents have the capacity to interact with the A-EDOT molecule. Especially, the hydrogens of the phenyl ring and the methoxy group in 2MA tend to interact with the oxygen atoms of carbonyl units in A-EDOT molecules, and the formation of hydrogen bonds stabilizes their interaction energy . Due to the intrinsic high polarity of the 2MA, the calculated absorption energy ( E abs ) between A-EDOT and 2MA is −0.308 eV, greater than that of the combination of A-EDOT and CB (−0.057 eV).…”

Section: Results and Discussionmentioning

confidence: 96%

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Flexible Backbone-Assisted Green-Solvent Processable Polymer Hole Transport Material in Perovskite Solar Cells

Zhao,

Zong,

Chen

et al. 2024

ACS Sustainable Chem. Eng.

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Developing green-solvent processable polymer hole transport materials (p-HTMs) is considered imperative for industrial-scale production. However, the introduction of a large conjugated structure into molecules that ensures strong intermolecular interactions as well as high hole mobility compromises their solubility in green solvents. Lacking solubility could result in excessive phase separation and heterogeneous thin films for p-HTMs, while it would sacrifice device performance. In order to address this trade-off, we propose an effective design strategy that combines backbone flexibility and rigid conjugate engineering modulation. The delicate collocation of flexible amide chains, polar solubilizing ethylenedioxythiophene (EDOT) units, and conjugated binaphthalene groups contributes to high hole mobility and multiple defect passivation effects. Moreover, the resulting p-HTM (A-EDOT) can be processed by the green solvent 2-methylanisole (2MA). Once used as an HTM in inverted perovskite solar cells, a significant fill factor (FF) of 81.9% and a champion efficiency of 20.23% are achieved for the A-EDOT, outperforming the state-ofthe-art polymer PTAA (FF = 80.5%, efficiency = 19.68%) that is processed with chlorobenzene. Moreover, due to the passivation effects of A-EDOT, the quality of perovskite films is improved; correspondingly, a significantly promoted long-term device stability and thermal stability are realized. This work provides a competitive design strategy of green-solvent processable p-HTMs for photovoltaic devices.

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Section: ■ Results and Discussionmentioning

confidence: 96%

Section: Results and Discussionmentioning

confidence: 96%

Flexible Backbone-Assisted Green-Solvent Processable Polymer Hole Transport Material in Perovskite Solar Cells

Zhao,

Zong,

Chen

et al. 2024

ACS Sustainable Chem. Eng.

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“…The parameters (Λ 12 , Λ 21 ) in eq can be calculated from V (pure component molar volume) and Δλ (characteristic energy difference); the model is suitable for calculating the activity coefficients of solutes , and is expressed as eqs –. where the model parameters Δλ 12 and Δλ 21 represent the characteristic energy difference, and their values can be determined by fitting the experimental data to the model . ρ and M represent the density and molar mass.…”

Section: Methodsmentioning

confidence: 99%

“…The parameters (Λ 12 , Λ 21 ) 32 in eq 12 can be calculated from V (pure component molar volume) and Δλ (characteristic energy difference); the model is suitable for calculating the activity coefficients of solutes 33,34 and is expressed 35 as eqs13−16.…”

Section: Solubility Measurementmentioning

confidence: 99%

Exploring the Dissolution Behavior of m-Hydroxybenzoic Acid in 14 Pure Solvents Using Thermodynamic, Molecular Simulation and Hansen Solubility Parameters

Liu,

Yang,

Shi

et al. 2023

J. Chem. Eng. Data

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In this study, the solubility of m-hydroxybenzoic acid in 14 organic pure solvents (acetone, iso-propanol, ethanol, n-propanol, methanol, ethylene glycol, n-pentanol, n-butanol, methyl acetate, n-propyl acetate, ethyl acetate, butyl acetate, iso-propyl acetate, acetonitrile) at the pressure of 0.1 MPa (at T = 278.15–323.15 K) was studied by the static weight method. The order of solubility (molar fraction) of m-hydroxybenzoic acid in the 14 pure solvents at 278.15 K was acetone > iso-propanol > ethanol > n-propanol > methanol > ethylene glycol > n-pentanol > n-butanol > methyl acetate > n-propyl acetate > ethyl acetate > butyl acetate > iso-propyl acetate > acetonitrile. As the temperature improved, the solubility correspondingly increased. The m-hydroxybenzoic acid solubility data in pure solvents were connected using the modified Apelblat model, the λh model, the NRTL model, and the Wilson model, and the best-fit performance was obtained using a modified Apelblat model. Performance was obtained using a modified Apelblat model. Two molecular dynamics analysis methods, Hirshfeld surface analysis and molecular electrostatic potential surface (MEP) analysis, were used to determine the dissolution process of m-hydroxybenzoic acid crystals and the interaction sites with solvent molecules in solution. The Hansen solubility parameters (HSPs) were utilized to assess the solvent’s capability and to elucidate its ability to dissolve m-hydroxybenzoic acid.

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“…Systems of solid−liquid equilibrium can be fitted using this semiempirical correlation equation. 42 The solubility data corrected with the λh equation can be given as follows:…”

Section: λH Equationmentioning

confidence: 99%

Measurement and Model Evaluation of Solubility of 2-(4-tert-Butylphenyl)-5-(4-biphenyl)-1,3,4-oxadiazole in Different Organic Solvents at Various Temperatures

Piao,

Guo,

Wang

et al. 2024

J. Chem. Eng. Data

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2-(4-tert-Butylphenyl)-5-(4-biphenyl)-1,3,4-oxadiazole (PBD) is one of the most widely used electron transport layer materials in optoelectronic devices, and studies on the solubility of PBD in various solvents are critical for development of solution-processable roll-to-roll electronic devices. In this study, the isothermal saturation method is used to determine the solubility data of PBD in 12 commonly used organic solvents. The experimental solubility of PBD increases gradually with enhanced temperature for the examined temperature range of 283.15−323.15 K in nhexane, methanol, ethanol, isopropanol, tetrahydrofuran (THF), acetonitrile, ethyl acetate, N-methylpyrrolidone (NMP), toluene, and chlorobenzene, while the temperature ranges were 293.15−333.15 K and 273.15−303.15 K for dimethyl sulfoxide and dichloromethane, respectively. The obtained solubility values of PBD are correlated by three models including the modified Apelblat equation, λh equation, and Yaws equation.Comparison of the calculated Akaike information criterion values resulted in selecting the optimal model for each solvent. Of the five solvents calculated, n-hexane, methanol, toluene, THF, and NMP, the λh equation provides an optimal fit. Both the modified Apelblat equation and the Yaws equation work well in chlorobenzene. Among the other six solvents, the fit of the Yaws equation is the best. These results of solubility provide the basic data for the synthesis of PBD nanoparticles via high-gravity-assisted antisolvent precipitation processing.

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Solubility behavior investigation of 1,4-cyclohexanedione in ten pure organic solvents by solubility measurement, correlation, DFT calculation and thermodynamic analysis

Cited by 10 publications

References 49 publications

Flexible Backbone-Assisted Green-Solvent Processable Polymer Hole Transport Material in Perovskite Solar Cells

Flexible Backbone-Assisted Green-Solvent Processable Polymer Hole Transport Material in Perovskite Solar Cells

Exploring the Dissolution Behavior of m-Hydroxybenzoic Acid in 14 Pure Solvents Using Thermodynamic, Molecular Simulation and Hansen Solubility Parameters

Measurement and Model Evaluation of Solubility of 2-(4-tert-Butylphenyl)-5-(4-biphenyl)-1,3,4-oxadiazole in Different Organic Solvents at Various Temperatures

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