Extended Y-Rule Method for the Characterization of the Aromatic Sextets in Cata-Condensed Polycyclic Aromatic Hydrocarbons

Oña-Ruales, Jorge O.; Ruiz‐Morales, Yosadara

doi:10.1021/jp510180j

Cited by 17 publications

(32 citation statements)

References 60 publications

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“…The smaller E g and ΔEL in TDI, as compared with NDI or PDI, are conducive to higher electronic conductivity as well as higher operating voltages during the charge–discharge processes. Additionally, aromatic compounds with the highest ratio of sextets are the most stable ones according to Clar's rule, [ 31 ] and thus, it was found that TDI possesses the highest ratio of sextets after the two electrons reduction, as compared to PDI and NDI. Apparently, these factors significantly affect the storage electron capability of electrode materials.…”

Section: Principles Of Aromatic Imide Electrode Materialsmentioning

confidence: 99%

Molecular Engineering of Aromatic Imides for Organic Secondary Batteries

Yin

Hei

et al. 2021

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Aromatic imides are a class of attractive organic materials with inherently electroactive groups and large π electron‐deficient scaffolds, which hold potential as electrode materials for organic secondary batteries (OSBs). However, the undecorated aromatic imides are usually plagued by low capacity, high solubility in electrolyte, and poor electronic/ionic conductivity. Molecular engineering has been demonstrated to be an effective strategy to address unsatisfying characteristics of the aromatic imides, thereby expanding their scope for applications in OSBs. In this review, the recent research progress in modulation of the capacity, dissolution, and electronic/ionic conductivity of aromatic imides for organic lithium batteries, organic sodium batteries, and redox flow batteries are summarized. In addition, the challenge and prospective of aromatic imides in organic secondary battery applications are also discussed.

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Section: Principles Of Aromatic Imide Electrode Materialsmentioning

confidence: 99%

Molecular Engineering of Aromatic Imides for Organic Secondary Batteries

Yin

Hei

et al. 2021

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“…They are the most aromatic centers in PAHs and indicate regions of local aromaticity in large molecules. , Consistent with the stability of aromatic rings resulting from electron delocalization, AS contribute to the kinetic stability of PAHs by increasing the HOMO–LUMO gap . IDB, on the other hand, have polyene-like character and can be as reactive as olefinic double bonds in unconjugated molecules. ,, The most probable electronic structure of a PAH is one in which the number of AS is maximized while the number of IDB is minimized, and algorithms such as the Y-rule have been developed to identify these electronic structures. ,− …”

Section: Results and Discussionmentioning

confidence: 99%

Carbon Core Electron Spectra of Polycyclic Aromatic Hydrocarbons

et al. 2018

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Aromaticity profoundly affects molecular orbitals in polycyclic aromatic hydrocarbons. X-ray core electron spectroscopy has observed that carbon 1s-π* transitions can be broadened or even split in some polycyclic systems, although the origin of the effect has remained obscure. The π electrons in polycyclic systems are typically classified in the Clar model as belonging to either true aromatic sextets (similar to benzene) or isolated double bonds (similar to olefins). Here, bulk-sensitive carbon core excitation spectra are presented for a series of polycyclic systems and show that the magnitude of the 1s-π* splitting is determined primarily by the ratio of true aromatic sextets to isolated double bonds. The observed splitting can be rationalized in terms of ground state energetics as described by Hückel, driven by the π electron structure described by Clar. This simple model including only ground state energetics is shown to explain the basics physics behind the spectral evolution for a broad set of polycyclic aromatic hydrocarbons, although some residual deviations between this model and experiment can likely be improved by including a more detailed electronic structure and the core hole effect.

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“…Of course, the dependency of the local aromaticity in polycyclic conjugated systems on the annelation manner -linear or angular -is not a new finding since the influence of annelation manner on the local aromaticity in benzenoid and nonbenzenoid polycyclic compounds have been studied in many recent papers. [92][93][94][95][96][97][98][99] Now, an interesting question is whether further annelation of the central benzene ring of 7 and 3 in the angular position by four-and six-membered ring, respectively, will increase the local aromaticity of the rings in these new compounds?…”

Section: Cyclobutadieno-annelated Benzenementioning

confidence: 99%

Characterization of Local Aromaticity in Polycyclic Conjugated Hydrocarbons Based on Anisotropy of π‐Electron Density

2017

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In recent contributions, it was demonstrated that the anisotropy of π‐electron density could be considered as a reliable descriptor to probe the aromaticity in a wide range of annulene and hetero‐monocyclic compounds. The electron density anisotropy on a plane can be simply measured by the ratio of two in‐plane Hessian eigenvalues associated with the eigenvectors lying in the plane. This descriptor is undirected and has a circular symmetry for aromatic rings, whereas it is directed and has an elliptical shape in antiaromatic cycles. This research takes a step forward towards the extension of this approach to polycyclic conjugated hydrocarbons. The obtained results show that the anisotropy of the π‐electron density works nicely for the assessment of local aromaticity in polycyclic compounds. This finding provides clear evidence to have a universally successful aromaticity descriptor based on the topological properties of one‐electron density distribution.

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Extended Y-Rule Method for the Characterization of the Aromatic Sextets in Cata-Condensed Polycyclic Aromatic Hydrocarbons

Cited by 17 publications

References 60 publications

Molecular Engineering of Aromatic Imides for Organic Secondary Batteries

Molecular Engineering of Aromatic Imides for Organic Secondary Batteries

Carbon Core Electron Spectra of Polycyclic Aromatic Hydrocarbons

Characterization of Local Aromaticity in Polycyclic Conjugated Hydrocarbons Based on Anisotropy of π‐Electron Density

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