Hydrogenated polycyclic aromatic hydrocarbons: isomerism and aromaticity

Pla, Paula; Wang, Yang; Martín, Fernando; Alcamı́, Manuel

doi:10.1039/d0cp04177g

Cited by 11 publications

(16 citation statements)

References 49 publications

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“…Finally, it is worth noticing that the most stable isomer of C 24 H 18 corresponds to the most stable isomer of hydrogenated coronene with six additional H atoms. 62 This is also the case of other low energy isomers found by the GA algorithm (three among five within 0.53 eV (see Figure S1c)), the two other isomers possessing methyl groups. Interestingly, regarding C 24 H 24 , the most stable isomer found by the GA algorithm possesses two methyl groups (see Figure 9 and Figure S1(d)) whereas the most stable isomer of hydrogenated coronene with 12 additional H atoms 62 was found 0.31 eV higher in energy after local SCC-DFTB optimization, and it has not been found with the GA algorithm.…”

Section: Resultssupporting

confidence: 52%

“…Interestingly, the 6 th isomer located 1.71 eV above coronene presents a fulvene function. Finally, it is worth noticing that the most stable isomer of C 24 H 18 corresponds to the most stable isomer of hydrogenated coronene with six additional H atoms . This is also the case of other low energy isomers found by the GA algorithm (three among five within 0.53 eV (see Figure S1c)), the two other isomers possessing methyl groups.…”

Section: Resultsmentioning

confidence: 54%

“…being 1.33 eV more stable than the next isomer found by GA.Finally, it is worth noticing that the most stable isomer of C 24 H 18 corresponds to the most stable isomer of hydrogenated coronene with 6 additional H atoms48 whereas the calculation of the most stable isomer of hydrogenated coronene with 12 additional H atoms 48 calculated…”

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confidence: 84%

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Hydrogenation of C₂₄ Carbon Clusters: Structural Diversity and Energetic Properties

et al. 2021

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This work aims at exploring the potential energy surfaces of C 24 H n=0, 6,12,18,24 up to 20-25 eV using the genetic algorithm in combination with the density functional based tight binding (DFTB) potential. The structural diversity of the non fragmented structures was analysed using order parameters which were chosen as the number of 5 or 6 member rings and the asphericity constant . The most abundant and lowest energy population was found to correspond to a fakes population, constituted of isomers of variable shapes possessing a large number of 5 or 6-carbon rings. This population is characterized by a larger number of spherical isomers when n H /n C increases. Simultaneously, the fraction of the pretzels population constituted of spherical isomers possessing fewer 5 or 6 carbon ring cycles increases. For all hydrogenation rates, the fraction of cages population, possessing the largest number of 5 or 6-carbon rings remains extremely minor while the branched population, characterized by the smallest number of 5 or 6-carbon rings, is the highest energy population for all n H /n C ratios. For all C 24 H n=0,6,12,18,24 clusters, a detailed study of the evolution of the carbon ring size distribution as a function of energy clearly shows that the stability is correlated to the number of 6-carbon rings. A similar study for hybridization sp n (n=1-3) shows that 3 the number of sp 1 carbon atoms increases with energy while globally the number of sp carbon atoms increases with n H /n C . The average values of the ionization potentials of all populations, obtained at the self-consistent charge DFTB level, were found to decrease when n H /n C increases, ranging from 7.9 eV down to 6.4 eV. We correlated this trend to geometric and electronic factors, in particular to carbon atoms hybridization n sp (n=1-3). These results are of astrophysical interest as they should be taken into account in astrophysical models especially regarding the role of carbonaceous species in the gas ionization.

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Section: Resultssupporting

confidence: 52%

Section: Resultsmentioning

confidence: 54%

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Hydrogenation of C₂₄ Carbon Clusters: Structural Diversity and Energetic Properties

et al. 2021

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“…The hydrogenation saturation of aromatic hydrocarbons is a key industrial process, [ 1–4 ] as transportation fuels with higher contents of aromatic hydrocarbons not only show worse combustion performance but also generate exhaust gases with more harmful products (e.g., polycyclic aromatic hydrocarbons and particulate matter). [ 4,5 ] Moreover, the excessive content of aromatic hydrocarbons in jet fuels can cause elastomer seal swelling.…”

Section: Introductionmentioning

confidence: 99%

“…The hydrogenation saturation of aromatic hydrocarbons is a key industrial process, [1][2][3][4] as transportation fuels with higher The acidity of the zeolite skeletal frame can also be exploited to provide active sites for the adsorption of aromatic hydrocarbons. [30] Thus, the selection of a proper support is important for enhancing catalyst activity, selectivity, and lifetime.…”

Section: Introductionmentioning

confidence: 99%

Selective Hydrogenation of Naphthalene to Decalin Over Surface‐Engineered α‐MoC Based on Synergy between Pd Doping and Mo Vacancy Generation

Liu

Chen

et al. 2022

Adv Funct Materials

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Although the hydrogenation of aromatics is important for the processing of fossil fuels and biofuels, it typically requires costly (e.g., noble metal‐based) catalysts and exhibits unsatisfactory selectivity. Herein, flake‐like nanocrystalline molybdenum carbide (α‐MoC) is surface‐engineered via Pd doping, and the synergy between the in‐situ generated Mo vacancies and doped Pd species is shown to promote the selective hydrogenation of naphthalene to decalin. Experimental and theoretical evidence reveal that this enhanced performance is due to the optimization of naphthalene adsorption energy and the establishment of a unique surface structure due to (i) surface environment modulation, (ii) the adjustment of electron density around Mo atoms, and (iii) the change in the strength of Mo‐H bonding caused by d‐band center optimization. Benefiting from the unique surface structure, the obtained optimum 0.5% Pd‐α‐MoC catalyst exhibits excellent performance. The developed strategy is successfully used to fabricate other noble metal (Pt, Ru)‐doped α‐MoC catalysts, thus holding promise as a universal method for the rational design of high‐performance metal carbide‐based hydrogenation catalysts.

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Single‐Molecule Cross‐Plane Conductance of Polycyclic Aromatic Hydrocarbon Derivatives

Yang,

Albalawi,

Zhao

et al. 2024

Chemistry A European J

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In the cross‐plane single‐molecule junctions, the correlation between molecular aromaticity and conductance remained puzzling. Cross‐plane break junction (XPBJ) provides new insight into understanding the role of aromaticity and conjugation to molecules on charge transport through the planar molecules. In this work, we investigated the modulation of cross‐plane charge transport in pyrene derivatives by hydrogenation and substituents based on the XPBJ method that differs from those used in‐plane transport. We measured the electrical conductance of the hydrogenated derivatives of the pyrenes and found that hydrogenation reduces conductance, and the fully hydrogenated molecule has the lowest conductance. Conductance of pyrene derivatives increased after substitution by both electron‐donating and electron‐withdrawing groups. By calculating, the trend in decreased conductance of hydrogenated pyrene was found to be consistent with the change in aromaticity. Electron‐withdrawing substituents reduce the aromaticity of the molecule and narrow the HOMO‐LUMO gap, while electron‐donating groups increase the aromaticity but also narrow the gap. Our work reveals the potential of fine‐tuning the structure of the pyrene molecule to control the cross‐plane charge transport through the single‐molecule junctions.

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Hydrogenated polycyclic aromatic hydrocarbons: isomerism and aromaticity

Abstract: A simple model based on adjacency matrices is introduced to study the stability of hydrogenated polycyclic aromatic hydrocarbons. Aromaticity governs their relative stability having the most stable isomers the higher number of non-hydrogenated rings.

Cited by 11 publications

References 49 publications

Hydrogenation of C₂₄ Carbon Clusters: Structural Diversity and Energetic Properties

Hydrogenation of C₂₄ Carbon Clusters: Structural Diversity and Energetic Properties

Selective Hydrogenation of Naphthalene to Decalin Over Surface‐Engineered α‐MoC Based on Synergy between Pd Doping and Mo Vacancy Generation

Single‐Molecule Cross‐Plane Conductance of Polycyclic Aromatic Hydrocarbon Derivatives

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Hydrogenated polycyclic aromatic hydrocarbons: isomerism and aromaticity

Abstract: A simple model based on adjacency matrices is introduced to study the stability of hydrogenated polycyclic aromatic hydrocarbons. Aromaticity governs their relative stability having the most stable isomers the higher number of non-hydrogenated rings.

Cited by 11 publications

References 49 publications

Hydrogenation of C24 Carbon Clusters: Structural Diversity and Energetic Properties

Hydrogenation of C24 Carbon Clusters: Structural Diversity and Energetic Properties

Selective Hydrogenation of Naphthalene to Decalin Over Surface‐Engineered α‐MoC Based on Synergy between Pd Doping and Mo Vacancy Generation

Single‐Molecule Cross‐Plane Conductance of Polycyclic Aromatic Hydrocarbon Derivatives

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Hydrogenation of C₂₄ Carbon Clusters: Structural Diversity and Energetic Properties

Hydrogenation of C₂₄ Carbon Clusters: Structural Diversity and Energetic Properties