Gear-Meshed Tiling of Surfaces with Molecular Pentagonal Stars

Stöckl, Quirin S.; Bandera, Davide; Kaplan, Craig S.; Ernst, Karl‐Heinz; Siegel, Jay S.

doi:10.1021/ja411279r

Cited by 22 publications

(20 citation statements)

References 38 publications

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“…Bowl-shaped polycyclic aromatic hydrocarbons, also named buckybowls, have attracted interest due to their unique chemical and physical properties, [1][2][3][4] such as bowl inversion, [5,6] supramolecular assembly, [7,8] electronic conductivity, [9,10] and chirality. [11,12] In the past decade, C 3v -symmetric sumanene [13,14] and C 5v -symmetric corannulene, [2,3] as the typical subunits of C 60 , have been intensively investigated.…”

Section: Supporting Information Placeholdermentioning

confidence: 99%

Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C₇₀ Containing Two Pentagons

Liu

Osella

et al. 2016

J. Am. Chem. Soc.

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Total synthetic approaches of fullerenes are the holy grail for organic chemistry. So far, the main attempts have focused on the synthesis of the buckminsterfullerene C60. In contrast, access to subunits of the homologue C70 remains challenging. Here, we demonstrate an efficient bottom-up strategy toward a novel bowl-shaped polycyclic aromatic hydrocarbons (PAH) C34 with two pentagons. This PAH represents a subunit for C70 and of other higher fullerenes. The bowl-shaped structure was unambiguously determined by X-ray crystallography. A bowl-to-bowl inversion for a C70 fragment in solution was investigated by dynamic NMR analysis, showing a bowl-to-bowl inversion energy (ΔG(⧧)) of 16.7 kcal mol(-1), which is further corroborated by DFT calculations.

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Section: Supporting Information Placeholdermentioning

confidence: 99%

Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C₇₀ Containing Two Pentagons

Liu

Osella

et al. 2016

J. Am. Chem. Soc.

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“…Other pioneering studies of liquid structure identified local fivefold symmetry, thus giving rise to the idea that it should have an important role in suppressing crystallization34. This concept of competition between fivefold symmetry in the liquid and sixfold crystalline symmetry underpins the design of materials as diverse as metallic glasses56, quantum liquids7, pentagonal molecules8 and colloidal polymers9.…”

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confidence: 99%

The role of fivefold symmetry in suppressing crystallization

Taffs

Royall

2016

Nat Commun

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Although long assumed to have an important role in the suppression of crystallization and the development of glassformers, the effect of local fivefold symmetry has never been directly tested. Here we consider whether such suppression of crystallization has a kinetic or thermodynamic nature and investigate its mechanism. We introduce a model in which the degree of fivefold symmetry can be tuned by favouring arrangements of particles in pentagonal bipyramids. We thus show that fivefold symmetry has both kinetic and thermodynamic effects on the mechanism of crystallization to a face-centred cubic crystal. Our results suggest that the mechanism of crystallization suppression is related to the surface tension between fluid and crystal. Interestingly, the degree of fivefold symmetry has little effect on crystal growth rate, suggesting that growth may be only weakly coupled to fluid structure in hard sphere like systems. Upon increasing the fivefold symmetry, we find a first-order transition to an alternative icosahedra-rich phase. At intermediate bias strengths we find a one-component glassformer.

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“…As mentioned above, the tiling of a flat surface with other C 5 corannulene molecules resulted in hexagonal arrays of those pentagonal star‐shaped molecules,, not pentagonal arrays of pentagons as in the ab planes in CORA‐5‐1 . Pentagonal arrays of objects of any shape, even molecules or supramolecular assemblages of molecules with fivefold or pseudo‐fivefold symmetry, are not commonly found in two‐ or three‐dimensional crystals because, as is well known, pentagonal arrays cannot tile space effectively .…”

Section: Resultsmentioning

confidence: 92%

Understanding Polyarene Trifluoromethylation with Hot CF₃ Radicals Using Corannulene

et al. 2018

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New insights into the process of high‐temperature trifluoromethylation of polycyclic aromatic hydrocarbons (PAHs) were gained in a detailed study of the reactions between corannulene (C20H10) and CF3I gas. Ten new poly(trifluoromethyl)corannulenes were made in these reactions and were fully characterized. A detailed computational study explains the observed trends in the product distribution and why some products cannot be prepared even with an excess of the reagent gas. The approach utilized here may have good predictive value for designing new effective and selective synthetic methodologies for various thermally stable electron‐deficient PAHs.

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Gear-Meshed Tiling of Surfaces with Molecular Pentagonal Stars

Cited by 22 publications

References 38 publications

Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C₇₀ Containing Two Pentagons

Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C₇₀ Containing Two Pentagons

The role of fivefold symmetry in suppressing crystallization

Understanding Polyarene Trifluoromethylation with Hot CF₃ Radicals Using Corannulene

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Gear-Meshed Tiling of Surfaces with Molecular Pentagonal Stars

Cited by 22 publications

References 38 publications

Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C70 Containing Two Pentagons

Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C70 Containing Two Pentagons

The role of fivefold symmetry in suppressing crystallization

Understanding Polyarene Trifluoromethylation with Hot CF3 Radicals Using Corannulene

Contact Info

Product

Resources

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Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C₇₀ Containing Two Pentagons

Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C₇₀ Containing Two Pentagons

Understanding Polyarene Trifluoromethylation with Hot CF₃ Radicals Using Corannulene