Edge modification of PAHs: the effect of embedded heterocycles on the aromaticity pattern

Synthesis and electronic properties of polycyclic aromatic hydrocarbons doped with phosphorus and sulfur

“…The non-aromatic (or slightly antiaromatic) character of the thiooxophosphole unit spreads toward the ring fused to its 3,4 position. 21 By increasing the number of the fused rings (3 → 5f; 4 → 6f ) the antiaromaticity of these rings strengthens in both series, but regardless of this phenomenon, in good agreement with the conclusions obtained from X-ray crystallography, the formed new rings are highly aromatic. This study confirms that insertion of an antiaromatic ring inside a PAH backbone impacts its properties.…”

Effect of Arsenic Coordination State on the Structure, Aromaticity, and Optical Properties of Dithieno[3,2‐b:2′,3′‐d]arsoles

“…This planarity results in a high degree of π‐conjugation in such systems, which has led to their use in conjugated polymers for organic electronics applications . Furthermore, the nature of the heteroatom in the central ring can have a large impact on the aromaticity of the resulting heterocycle . For example, in dithieno[3,2‐ b :2′,3′‐ d ]pyrrole the lone pair of the nitrogen atom is fully conjugated (similar to pyrrole), giving a high degree of aromaticity.…”

Phosphorus‐Containing Polycyclic Aromatic Hydrocarbons

“…The investigation of the local NICS aromaticities in the heterole-modified PAHs revealed that the aromaticc haracterc ould indeed be varied, over ab road range. [56] Importantly,t here is ag ood correlation between the NICS(1)v alues of the built-in heterocyclesa nd those of the isolated rings ( Figure 9);t his also indicates the appropriateness of using NICS as al ocal aromaticity measure. It is noteworthy that not only the NICS(1) values of the five-mem- (Figure 9).…”