Analogy between sulfuryl and phosphino groups: the aromaticity of thiophene-oxide

Hollóczki, Oldamur; Nyulászi, László

doi:10.1007/s11224-011-9834-8

Cited by 12 publications

(5 citation statements)

References 63 publications

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“…Aromaticity Before investigating the extended systems, the aromaticity of the parent rings (Table 1) has been calculated at the highest used level of theory (B3LYP/cc-pVTZ). The results (summarized in Table 1) are in good agreement with the values published previously at a somewhat different level of theory [42]. As expected, NICS(1) values span a wide range between -10.7 for tiophene, a highly aromatic ring and +11.6 for antiaromatic borole.…”

Section: Resultssupporting

confidence: 90%

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

et al. 2015

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Section: Resultssupporting

confidence: 90%

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

et al. 2015

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“…Computed results given in Table show that all compounds considered are aromatic systems with negative NICS values. Previous reports showed that the aromaticity of furan is slightly reduced as compared to those of thiophene and selene. , However, our predictions in this context reveal an opposite trend. The NICS values obtained at the center of furan are systemically more negative than those obtained at the centers of thiophene and selene.…”

Section: Resultscontrasting

confidence: 77%

π-Conjugated Molecules Containing Naphtho[2,3-b]thiophene and Their Derivatives: Theoretical Design for Organic Semiconductors

et al. 2013

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We performed a theoretical investigation on a series of π-conjugated organic molecules containing naphtho[2,3-b]thiophene and their derivatives using density functional theory calculations. All molecules considered exhibit planar structures and aromaticity. Energy levels of frontier orbitals and reduction and oxidation potentials of these compounds predicted by our solvation model reveal good agreement with available experimental values. The UV absorption spectra point out a clear trend that maximum peaks corresponding HOMO–LUMO transitions are red-shifted: (i) from compounds containing O to those containing Se, (ii) from dimers 1a–3a and 1b–3b to trimers 4a–6a and 4b–6b, and (iii) from parent compounds 1a–6a to perfluorinated derivatives 1b–6b. Parent compounds 1a–6a can be considered as p-type semiconducting materials with low reorganization energies, high transfer integrals, and hole mobility. Perfluorinated compounds 1b–6b are suggested to be very good candidates for ambipolar semiconducting materials. Introduction of fused-ring core molecules considerably improves the charge transport characteristics of the co-oligomers 4a–6a and 4b–6b as compared to those of corresponding molecules 1a–3a and 1b–3b. Accordingly, the former have lower reorganization energies, higher electron transfer integrals, and higher rates of charge hopping.

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“…NICS values [22] are collected in Ta ble S7, and are presentedi nF igure 6, in which the size of the circles is proportionalt ot he NICS(1) value, black represents antiaromatic, whereas gray denotes aromatic ring current (NICS(0) shows as imilar behavior,s ee Figure S13). It is known that phosphole-sulfides are slightly antiaromatic [23] (in general,o xidation of second row heteroatoms such as phosphoruso rs ulfur decreases the aromaticity), [24] and accordingly the five-membered rings are antiaromatic for the entire series. More interestingly, the endocyclics ix-membered ring fused with the five-membered ring also becamea ntiaromatic, throughout the entire series!W ith the increasinge xtent of the conjugation,t he antiaromaticity shows some increaset hroughout the series 2a S -3a S -4a S ,a lthough the values remain small; for example, in case of NICS(1), the value for the endocyclic six-membered ring is + 3.0.…”

Section: Theoretical Calculationsmentioning

confidence: 99%

Synthesis, Electronic Properties and WOLED Devices of Planar Phosphorus‐Containing Polycyclic Aromatic Hydrocarbons

Riobé

Szűcs

Bouit

et al. 2015

Chemistry A European J

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Abstract:The article deals with the synthesis and the physical properties of polyaromatic hydrocarbons containing P-atom at the edge. In particular, the impact of the successive addition of aromatic rings on the electronic properties was investigated by experimental (UV-vis absorption, fluorescence, cyclic voltammetry) and theoretical studies (DFT). The physical properties recorded in solution and in solid state showed that the P-containing PAHs exhibit the expected properties to be used as emitter in WOLEDs.

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Analogy between sulfuryl and phosphino groups: the aromaticity of thiophene-oxide

Cited by 12 publications

References 63 publications

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

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

π-Conjugated Molecules Containing Naphtho[2,3-b]thiophene and Their Derivatives: Theoretical Design for Organic Semiconductors

Synthesis, Electronic Properties and WOLED Devices of Planar Phosphorus‐Containing Polycyclic Aromatic Hydrocarbons

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