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Thermodynamics of Organic Materials

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Physical Chemistry".

Deadline for manuscript submissions: 31 December 2024 | Viewed by 8003

Special Issue Editors

Dr. Carlos Lima

E-Mail Website
Guest Editor
Research Centre in Chemistry (CIQUP), Institute of Molecular Sciences (IMS), Department of Chemistry and Biochemistry, Faculty of Sciences of University of Porto, P-4169-007 Porto, Portugal
Interests: molecular structure and energetics; aromatic interactions; electronic conjugation in aromatic molecules; physicochemical properties of fullerenes; molecular symmetry and entropy; organic semiconductor compounds; protic ionic liquids; mechanism of Suzuki-Miyaura cross-coupling reaction; phase change kinetics
Dr. Ana Rita Almeida

E-Mail Website
Guest Editor
Research Centre in Chemistry (CIQUP), Institute of Molecular Sciences (IMS), Department of Chemistry and Biochemistry, Faculty of Sciences of University of Porto, P-4169-007 Porto, Portugal
Interests: physical chemistry; thermodynamics; vapor pressures; phase transitions; intermolecular interactions; thermodynamic stability; development of models for estimating thermodynamic properties of organic compounds as they relate to their environment mobility

Special Issue Information

Dear Colleagues,

Organic compounds are traditionally related to life. Modern science, however, has shown that their role in our lives goes well beyond living matter. The advent of polymers, organic semiconductors, and ionic liquids, to name a few, have established the great value of organic materials in “inorganic” technology. The molecular thermodynamic approach is a crucial tool to understand why and how organic compounds become organic functional materials. For example, the knowledge of thermal stability and phase behavior allows an efficient screening of which compounds can be used under which conditions; molecular properties like electronic conjugation are relevant indicators for potential new candidates as organic semiconductors; substituents can be used to tune the stability, electronic structure, and solubility of organic compounds; aromatic interactions and the supramolecular structure dictate the efficiency of charge transport across an organic solid.

This Special Issue seeks to highlight the path that goes from the molecular understanding of organic compounds to their performance as functional materials. To this end, we will be welcoming contributions addressing the following topics: a) Synthesis and characterization of organic materials; b) Thermodynamic properties as determined by experimental and/or computational methods; c) Rationalization of molecular properties of organic compounds in view of their application in organic semiconductor devices and as functional materials. By bringing together the expertise from complementary areas under a “synthesize/understand/apply” philosophy, this Special Issue builds on the notion that the best guide for successful technology is fundamental knowledge.

Dr. Carlos Lima
Dr. Ana Rita Almeida
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • chemical thermodynamics
  • phase equilibrium
  • molecular structure and energetics
  • supramolecular chemistry
  • aromatic interactions
  • electronic correlation
  • organic semiconductors
  • functional materials

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Published Papers (7 papers)

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Research

20 pages, 4403 KiB  
Article
Estimation of the Vaporization Enthalpies and Vapor Pressures of α-Tocopherol and Δ9-Tetrahydrocannabinol via the Use of a Surrogate, Correlation Gas Chromatography, and Synthetic and Retrosynthetic Analysis
by Carissa Nelson, Christian Fischer-Lodike and James S. Chickos
Molecules 2024, 29(18), 4332; https://doi.org/10.3390/molecules29184332 - 12 Sep 2024
Viewed by 598
Abstract
A protocol is proposed that combines the use of the known properties of a surrogate containing various functional groups together with n-alkanes as standards to evaluate the properties of much larger related substances using correlation gas chromatography. An objective of this work is [...] Read more.
A protocol is proposed that combines the use of the known properties of a surrogate containing various functional groups together with n-alkanes as standards to evaluate the properties of much larger related substances using correlation gas chromatography. An objective of this work is to develop options that circumvent the lack of appropriate vaporization enthalpy standards that can be used for evaluation of various thermodynamic properties of larger complex molecules using gas chromatography. The surrogate in this case is 2,2,5,7,8-pentamethylchroman-6-ol (PMC) and is used to evaluate the vaporization enthalpies and vapor pressures of α-tocopherol (α-TOC) and Δ9-tetrahydrocannabinol (Δ9-THC). The results are compared to the available literature data and to estimated properties. Vaporization enthalpies are also evaluated by a proposed method that involves the use of synthetic and retrosynthetic analysis. Full article
(This article belongs to the Special Issue Thermodynamics of Organic Materials)
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13 pages, 896 KiB  
Article
Thermodynamic Study of 1,4-Bis(3-methylimidazolium-1-yl)butane Bis(trifluoromethylsulfonyl)imide ([C4(MIm)2][NTf2]2) from 6 to 350 K
by Alexey V. Markin, Andrea Ciccioli, Andrea Lapi, Semen S. Sologubov, Natalia N. Smirnova and Stefano Vecchio Ciprioti
Molecules 2024, 29(17), 4180; https://doi.org/10.3390/molecules29174180 - 3 Sep 2024
Viewed by 516
Abstract
The molar heat capacity of 1,4-bis(3-methylimidazolium-1-yl)butane bis(trifluoromethylsulfonyl)imide dicationic ionic compound ([C4(MIm)2][NTf2]2) has been studied over the temperature range from 6 to 350 K by adiabatic calorimetry. In the above temperature interval, this compound has been [...] Read more.
The molar heat capacity of 1,4-bis(3-methylimidazolium-1-yl)butane bis(trifluoromethylsulfonyl)imide dicationic ionic compound ([C4(MIm)2][NTf2]2) has been studied over the temperature range from 6 to 350 K by adiabatic calorimetry. In the above temperature interval, this compound has been found to form crystal, liquid, and supercooled liquid. For [C4(MIm)2][NTf2]2, the temperature of fusion T°fus = (337.88 ± 0.01) K has been determined by the fractional melting experiments, the enthalpy of fusion ΔfusH° = (52.79 ± 0.28) kJ mol−1 has been measured using the calorimetric method of continuous energy input, and the entropy of fusion ΔfusS° = (156.2 ± 1.7) J K−1 mol−1 has also been evaluated. The standard thermodynamic functions of the studied dicationic ionic compound, namely, the heat capacity Cp°(T), the enthalpy [H°(T) − H°(0)], the entropy S°(T) and the Gibbs free energy [G°(T) − H°(0)] have been calculated on the basis of the experimental data for the temperature range up to 350 K. The results have been discussed and compared with those available in the literature and in the NIST Ionic Liquids Database (ILThermo) for monocationic ionic compounds. Full article
(This article belongs to the Special Issue Thermodynamics of Organic Materials)
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16 pages, 2289 KiB  
Article
Liquid–Liquid Equilibrium of Sesame Fatty Acid (Ethyl and Methyl) Ester + Glycerol + Ethanol/Methanol Mixtures at Different Temperatures
by Anderson Silva, Guilherme Lopes, Marcos Corazza, Pedro Arce, Dayana Coêlho, Lucas Meili, Sandra Carvalho, Leandro Ferreira-Pinto and João Soletti
Molecules 2024, 29(13), 3167; https://doi.org/10.3390/molecules29133167 - 3 Jul 2024
Cited by 1 | Viewed by 1087
Abstract
This study aimed to investigate the liquid–liquid equilibrium (LLE) behavior of sesame fatty acid ethyl ester (FAEE) and methyl ester (FAME) in combination with glycerol and the co-solvents ethanol and methanol. FAEE and FAME were produced through the transesterification of mechanically extracted and [...] Read more.
This study aimed to investigate the liquid–liquid equilibrium (LLE) behavior of sesame fatty acid ethyl ester (FAEE) and methyl ester (FAME) in combination with glycerol and the co-solvents ethanol and methanol. FAEE and FAME were produced through the transesterification of mechanically extracted and purified sesame oil, using potassium hydroxide (KOH) as a homogeneous base catalyst. The reactions were conducted in ethanol and methanol to produce FAEE and FAME, respectively. Post-reaction, the products were separated and purified, followed by an analysis of the LLE behavior at 313.15 K and 323.15 K under atmospheric pressure (101.3 kPa). The experimental process for the miscibility analysis utilized a jacketed glass cell adapted for this study. Miscibility limits or binodal curves were determined using the turbidity-point method. Tie lines were constructed by preparing mixtures of known concentrations within the two-phase region, which allowed the phases to separate after agitation. Samples from both phases were analyzed to determine their composition. This study revealed that higher temperatures promoted greater phase separation and enhanced the biodiesel purification process. The NRTL model effectively correlated the activity coefficients with the experimental data, showing good agreement, with a root-mean-square deviation of 3.5%. Additionally, the data quality was validated using Marcilla’s method, which yielded an R2 value close to 1. Attraction factors and distribution coefficients were also calculated to evaluate the efficiency of the co-solvents as extraction agents. The findings indicated higher selectivity for methanol than for ethanol, with varying degrees of distribution among the co-solvents. These results offer significant insights into enhancing biodiesel production processes by considering the effects of co-solvents on the LLE properties of mixtures, ultimately contributing to more efficient and cost-effective biodiesel production. Full article
(This article belongs to the Special Issue Thermodynamics of Organic Materials)
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14 pages, 1881 KiB  
Article
Thermochemical Research on Furfurylamine and 5-Methylfurfurylamine: Experimental and Computational Insights
by Luísa M. P. F. Amaral, Ana R. R. P. Almeida and Manuel A. V. Ribeiro da Silva
Molecules 2024, 29(12), 2729; https://doi.org/10.3390/molecules29122729 - 7 Jun 2024
Viewed by 820
Abstract
The need to transition from fossil fuels to renewables arises from factors such as depletion, price fluctuations, and environmental considerations. Lignocellulosic biomass, being abundant, and quickly renewable, and not interfering with food supplies, offers a standout alternative for chemical production. This paper explores [...] Read more.
The need to transition from fossil fuels to renewables arises from factors such as depletion, price fluctuations, and environmental considerations. Lignocellulosic biomass, being abundant, and quickly renewable, and not interfering with food supplies, offers a standout alternative for chemical production. This paper explores the energetic characteristics of two derivatives of furfural—a versatile chemical obtained from biomass with great potential for commercial sustainable chemical and fuel production. The standard (p° = 0.1 MPa) molar enthalpies of formation of the liquids furfurylamine and 5-methylfurfurylamine were derived from the standard molar energies of combustion, determined in oxygen and at T = 298.15 K, by static bomb combustion calorimetry. Their standard molar enthalpies of vaporization were also determined at the same temperature using high-temperature Calvet microcalorimetry. By combining these data, the gas-phase enthalpies of formation at T = 298.15 K were calculated as −(43.5 ± 1.4) kJ·mol−1 for furfurylamine, and −(81.2 ± 1.7) kJ·mol−1 for 5-methylfurfurylamine. Furthermore, a theoretical analysis using G3 level calculations was performed, comparing the calculated enthalpies of formation with the experimental values to validate both results. This method has been successfully applied to similar molecules. The discussion looks into substituent effects in terms of stability and compares them with similar compounds. Full article
(This article belongs to the Special Issue Thermodynamics of Organic Materials)
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13 pages, 1066 KiB  
Article
Phase Transition Thermodynamics of 1,3,5-Tris-(α-naphthyl)benzene: Theory and Experiment
by Mikhail I. Yagofarov, Dmitrii N. Bolmatenkov, Airat A. Notfullin, Andrey A. Sokolov, Ilya S. Balakhontsev, Timur A. Mukhametzyanov and Boris N. Solomonov
Molecules 2024, 29(10), 2180; https://doi.org/10.3390/molecules29102180 - 7 May 2024
Viewed by 851
Abstract
1,3,5-Tris-(α-naphthyl)benzene is an organic non-electrolyte with notable stability of an amorphous phase. Its glassy and supercooled liquid states were previously studied by spectroscopic and calorimetric methods. Despite the continuing interest in its amorphous state and, particularly, vapor-deposited glasses, the thermodynamic parameters of the [...] Read more.
1,3,5-Tris-(α-naphthyl)benzene is an organic non-electrolyte with notable stability of an amorphous phase. Its glassy and supercooled liquid states were previously studied by spectroscopic and calorimetric methods. Despite the continuing interest in its amorphous state and, particularly, vapor-deposited glasses, the thermodynamic parameters of the vaporization of 1,3,5-tris-(α-naphthyl)benzene have not been obtained yet. Likewise, the reliable evaluation of the thermodynamic parameters of fusion below the melting point, required to establish the thermodynamic state of its glass, is still an unsolved problem. In this work, the heat capacities of crystalline and liquid phases, the temperature dependence of the saturated vapor pressures, fusion and vaporization enthalpies were determined using differential and fast scanning calorimetry and were verified using the estimates based on solution calorimetry. The structural features of 1,3,5-tris-(α-naphthyl)benzene are discussed based on the computations performed and the data on the molecular refractivity. The consistency between the values obtained by independent techniques was demonstrated. Full article
(This article belongs to the Special Issue Thermodynamics of Organic Materials)
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Graphical abstract

20 pages, 16184 KiB  
Article
Thermodynamic Study of N-Methylformamide and N,N-Dimethyl-Formamide
by Květoslav Růžička, Vojtěch Štejfa, Ctirad Červinka, Michal Fulem and Jiří Šturala
Molecules 2024, 29(5), 1110; https://doi.org/10.3390/molecules29051110 - 1 Mar 2024
Viewed by 1303
Abstract
An extensive thermodynamic study of N-methylformamide (CAS RN: 123-39-7) and N,N-dimethylformamide (CAS RN: 68-12-2), is presented in this work. The liquid heat capacities of N-methylformamide were measured by Tian–Calvet calorimetry in the temperature interval (250–300) K. The vapor [...] Read more.
An extensive thermodynamic study of N-methylformamide (CAS RN: 123-39-7) and N,N-dimethylformamide (CAS RN: 68-12-2), is presented in this work. The liquid heat capacities of N-methylformamide were measured by Tian–Calvet calorimetry in the temperature interval (250–300) K. The vapor pressures for N-methylformamide and N,N-dimethylformamide were measured using static method in the temperature range 238 K to 308 K. The ideal-gas thermodynamic properties were calculated using a combination of the density functional theory (DFT) and statistical thermodynamics. A consistent thermodynamic description was developed using the method of simultaneous correlation, where the experimental and selected literature data for vapor pressures, vaporization enthalpies, and liquid phase heat capacities and the calculated ideal-gas heat capacities were treated together to ensure overall thermodynamic consistency of the results. The resulting vapor pressure equation is valid from the triple point to the normal boiling point temperature. Full article
(This article belongs to the Special Issue Thermodynamics of Organic Materials)
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28 pages, 6956 KiB  
Article
Nearest-Neighbour and Non-Nearest-Neighbour Non-Covalent Interactions between Substituents in the Aromatic Systems: Experimental and Theoretical Investigation of Functionally Substituted Benzophenones
by Artemiy A. Samarov, Stanislav O. Kondratev and Sergey P. Verevkin
Molecules 2022, 27(23), 8477; https://doi.org/10.3390/molecules27238477 - 2 Dec 2022
Viewed by 1422
Abstract
Benzophenone derivatives exhibit not only biological activity but also act as photo initiator and UV blocker. We carried out experimental and theoretical thermochemical studies of hydroxy- and methoxy-substituted benzophenones. Standard molar enthalpies of vaporisation were obtained from the temperature dependence of vapour pressures [...] Read more.
Benzophenone derivatives exhibit not only biological activity but also act as photo initiator and UV blocker. We carried out experimental and theoretical thermochemical studies of hydroxy- and methoxy-substituted benzophenones. Standard molar enthalpies of vaporisation were obtained from the temperature dependence of vapour pressures measured by the transpiration method. The thermodynamic data on phase transitions available in the literature (crystal–gas, crystal–liquid, and liquid–gas) were also collected and evaluated. High-level quantum chemical methods G3MP2 and G4 were used to estimate the standard molar enthalpies of formation of substituted benzophenones in the gas phase and establish agreement between experimental and theoretical results. The application of the “centrepiece” group-contribution approach to hydroxy- and methoxy-substituted benzophenones was demonstrated. A quantitative assessment of the hydrogen bond was carried out using various approaches based on experimental data and quantum chemical calculations. Full article
(This article belongs to the Special Issue Thermodynamics of Organic Materials)
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