Polyhedral Phenylacetylenes: The Interplay of Aromaticity and Antiaromaticity in Convex Graphyne Substructures

Sebastiani, Daniel; Parker, Matt A.

doi:10.3390/sym1020226

Cited by 8 publications

(8 citation statements)

References 49 publications

(50 reference statements)

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“…3.24) and the alternating aromatic and antiaromatic moieties (Fig. Similar quantifying results were obtained for 5-and 6-membered aromatic heterocycles, their benzo analogues, of the cyclopropenylium cation, azulene, ferrocene, the [14]-and [18]-annulenes, and of the helicenes were published [55]. Similar quantifying results were obtained for 5-and 6-membered aromatic heterocycles, their benzo analogues, of the cyclopropenylium cation, azulene, ferrocene, the [14]-and [18]-annulenes, and of the helicenes were published [55].…”

Section: Application Of Tsnmrs In Quantificationsupporting

confidence: 79%

“…Sebastiani and Parker [14] presented NICS maps which consist of 2D slices of the 3D space of NICS values; NICS were made visible by different isosurfaces. Sebastiani and Parker [14] presented NICS maps which consist of 2D slices of the 3D space of NICS values; NICS were made visible by different isosurfaces.…”

Section: Computation and Visualization Of The Anisotropy Effect By Tsmentioning

confidence: 99%

“…3.27). Proved by the anisotropy/ring-current effect of the macrocyclic ring of carbo-benzene on the phenyl protons in 1 H NMR in mono-phenyl carbobenzene 15 and of the same effect of the 14-membered macrocyclic ring of dehydro [14]annulene on the phenyl protons of o,o 0 -ring included para-cyclophane protons in 1 H NMR (which are the molecular response property of spatial NICS-TSNMRS) the aromaticity of dehydro[10]-, dehydro [14]-(cf. The same is true for the corresponding tris-, penta-, hepta-and nonafulenes [60].…”

Section: Aromaticity Of Fulvenes Fulvalenes Dehydroannulenes and Fumentioning

confidence: 99%

“…14 Ground state conformer of 9-arylfluorene 7 (right) and visualization of the magnetic properties (TSNMRS, left) of the fluorene moiety as ICSS of different direction and size. Copyright 2011 Elsevier[36].…”

mentioning

confidence: 99%

“…28 Visualization of the spatial magnetic properties (TSNMRS) of the dehydro[14]annulene derivatives with increasing number of annelated phenyl moieties as ICSS (+2 ppm) shielding. Copyright 2013 Elsevier[62].…”

mentioning

confidence: 99%

See 4 more Smart Citations

Quantification and Visualization of the Anisotropy Effect in NMR Spectroscopy by Through-Space NMR Shieldings

Kleinpeter

2014

Annual Reports on NMR Spectroscopy

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Section: Application Of Tsnmrs In Quantificationsupporting

confidence: 79%

Section: Computation and Visualization Of The Anisotropy Effect By Tsmentioning

confidence: 99%

Section: Aromaticity Of Fulvenes Fulvalenes Dehydroannulenes and Fumentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Quantification and Visualization of the Anisotropy Effect in NMR Spectroscopy by Through-Space NMR Shieldings

Kleinpeter

2014

Annual Reports on NMR Spectroscopy

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A Study of π–π Stacking Interactions and Aromaticity in Polycyclic Aromatic Hydrocarbon/Nucleobase Complexes

Trujillo

Sánchez‐Sanz

2015

ChemPhysChem

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We analysed the interactions and aromaticity electron-density delocalisation observed in π-π complexes between the phenalenyl radical and acenaphthylene, and the DNA and RNA nucleobases (adenine, guanine, cytosine, thymine and uracil). Interaction energies are obtained at the M06-2X/6-311++G(2df,p) computational level for gas phase and PCM-water conditions. For both the phenalenyl radical and acenaphthylene, the complexes formed with guanine are the most stable ones. Atoms in molecules and natural bond orbital results reveal weak π-π interactions between both interacting moieties, characterized by bond critical points between C⋅⋅⋅C and C⋅⋅⋅N atoms. Nucleus independent chemical shifts (NICS) indicate the retention of the aromatic character of the monomers in the outer region of the complex. The fluctuation indexes reveal a loss of electron delocalisation upon complexation for all cases except guanine complexes. Nevertheless, the interface region shows large negative NICS values, which is not associated with an increase of the aromaticity or electron-density delocalisation, but with magnetic couplings of both molecules, leading to an unrealistic description of the aromatic behaviour in that region.

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On the Compressibility Properties of the Wine‐Rack‐Like Carbon Allotropes and Related Poly(phenylacetylene) Systems

Degabriele

Attard

Grima‐Cornish

et al. 2018

Physica Status Solidi (b)

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Poly(phenylacetylene) sheets that mimic the geometry of a wine-rack-like structure have been predicted to exhibit negative Poisson's ratios off-axis. However, their potential to exhibit negative linear compressibility (NLC) has remained largely unexplored. In this work, the compressibility and other mechanical properties of wine-rack-like poly(phenylacetylene) networks with 1,2,4,5 tetra-substituted phenyls as well as their equivalent with allene or cyclobutadiene centres are simulated to assess their ability to exhibit negative linear compressibility on-axis and off-axis. It is shown that some of these systems can indeed exhibit negative linear compressibility whilst others exhibit a near-zero compressibility. The results are compared to the compressibility properties of other poly(phenylacetylene) networks reported in literature as well as with those predicted from the analytical model for an idealised wine-rack structure deforming through hinging. Results suggest that these mechanical properties are arising from a wine-rack-like mechanism, and there is a good agreement with the theoretical model, especially for systems with longer acetylene chains whose geometry is closer to that of the idealised wine-rack.

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Polyhedral Phenylacetylenes: The Interplay of Aromaticity and Antiaromaticity in Convex Graphyne Substructures

Cited by 8 publications

References 49 publications

Quantification and Visualization of the Anisotropy Effect in NMR Spectroscopy by Through-Space NMR Shieldings

Quantification and Visualization of the Anisotropy Effect in NMR Spectroscopy by Through-Space NMR Shieldings

A Study of π–π Stacking Interactions and Aromaticity in Polycyclic Aromatic Hydrocarbon/Nucleobase Complexes

On the Compressibility Properties of the Wine‐Rack‐Like Carbon Allotropes and Related Poly(phenylacetylene) Systems

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