Monolayer structures of 4,4′ bipyridine on graphite at sub-monolayer coverage

Clarke, Stuart M.; Friščić, Tomislav; Mandal, Anasuya; Sun, Chengguo; Parker, Julia

doi:10.1080/00268976.2010.531296

Cited by 8 publications

(20 citation statements)

References 16 publications

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“…Recently, we have characterized the monolayer structures of 4,4'-bipyridyl (bpy) [16] and 1,2-bis(4-pyridyl)ethylene (bpe) [17] using synchrotron X-ray diffraction. These are illustrated in Figure 1 and are important species -with the overlayer crystal structures suggesting the formation of weak hydrogen bonds -as well as key components in halogen bonded molecular co-crystals [18].…”

Section: Introductionmentioning

confidence: 99%

The crystalline structure of the phenazine overlayer physisorbed on a graphite surface

et al. 2013

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The monolayer crystal structure of phenazine adsorbed on graphite is determined by a combination of synchrotron X-ray diffraction and DFT calculations. The molecules adopt a rectangular unit cell with lattice parameters a = 13.55 Å and b = 10.55 Å, which contains 2 molecules. The plane group of the unit cell is p2gg, and each molecule is essentially flat to the plane of the surface, with only a small amount of out-of-plane tilt. Density functional theory (DFT) calculations find a minimum energy structure with a unit cell which agrees within 7.5% with that deduced by diffraction. DFT including dispersion force corrections (DFT+D) calculations help to identify the nature of the intermolecular bonding. The overlayer interactions are principally van der Waals, with a smaller contribution from weak C-H···N hydrogen bonds. This behaviour is compared with that of 4,4′-bipyridyl

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Section: Introductionmentioning

confidence: 99%

The crystalline structure of the phenazine overlayer physisorbed on a graphite surface

et al. 2013

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“…It is not uncommon for molecules to adopt monolayer structures that approximate faces from their three-dimensional crystals [7,15], and in this current case the monolayer structure of bpe is similar to the [20-1] layer of the bulk crystal [17] (Cambridge Crystallographic Data Centre reference code AZSTBB; Figure 4(b)). Similarly to the monolayer, molecules in the bulk structure also only form a single nonbifurcated hydrogen bond between pyridine rings.…”

Section: Discussionmentioning

confidence: 91%

“…The herringbone structure very closely resembles the monolayer structure of the related molecule 4,4 0 -bipyridyl (BPY), which has a rectangular cell with pgg symmetry [7]. This molecule was also proposed to form C-H � � � N hydrogen bonds in the monolayer (although in the case of BPY the bonds are bifurcated) with a C to N distance of 3.61 Å , 3.66 Å and 3.69 Å , which are comparable to the distances found for bpe.…”

Section: Discussionmentioning

confidence: 93%

“…This contrasts with many sub-monolayer coverage physisorbed layers, which show melting points lowered by a greater degree relative to the bulk, typically by a factor of approximately 0.75. While some molecules do form solid monolayers close to, or indeed on rare occasions above [5,7,12], the bulk melting point even at sub-monolayer coverages, such layers are normally stabilized by strong intermolecular interactions like hydrogen bonds [5,12].…”

Section: Discussionmentioning

confidence: 99%

“…In addition, these molecules have been shown to form ordered single-component monolayers, whose structure is guided by the formation of weak C-H � � � N hydrogen bonds [6,7].…”

Section: Introductionmentioning

confidence: 99%

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The monolayer structure of 1,2-bis(4-pyridyl)ethylene physisorbed on a graphite surface

Brewer¹,

Friščić²,

Day³

et al. 2012

Molecular Physics

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The crystalline monolayer of 1,2-bis(4-pyridyl)ethylene physisorbed on a graphite surface at 0.44 monolayers coverage has been observed and characterized by synchrotron X-ray diffraction and differential scanning calorimetry. The experimentally determined monolayer structure has p2 symmetry with lattice parameters a ¼ 17.77 Å , b ¼ 13.69 Å and ¼ 39.7 � . The unit cell contains two molecules, which are oriented in a plane parallel to the surface. It is proposed that the molecules are arranged such that they are able to form a weak C-H � � � N hydrogen bond between pyridine groups. The monolayer melts at 414 K, which is unusually close to the bulk melting point for a sub-monolayer coverage system. This molecule is chiral when adsorbed on the surface, but both isomers appear in the unit cell leading to no overall chirality in the monolayer.

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Halogen Bonding in Bicomponent Monolayers: Self-Assembly of a Homologous Series of Iodinated Perfluoroalkanes with Bipyridine

et al. 2021

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A homologous series of halogen bonding monolayers based on terminally iodinated perfluoroalkanes and 4,4′-bipyridine have been observed on a graphitic surface and noninvasively probed using powder X-ray diffraction. An excellent agreement is observed between the X-ray structures and density functional theory calculations with dispersion force corrections. Theoretical analysis of the binding energies of the structures indicate that these halogen bonds are strong (25 kJ mol –1 ), indicating that the layers are highly stable. The monolayer structures are found to be distinct from any plane of the corresponding bulk structures, with limited evidence of partitioning of hydrocarbon and perfluoro tectons. The interchain interactions are found to be slightly stronger than those in related aromatic systems, with important implications for 2D crystal engineering.

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Monolayer structures of 4,4′ bipyridine on graphite at sub-monolayer coverage

Cited by 8 publications

References 16 publications

The crystalline structure of the phenazine overlayer physisorbed on a graphite surface

The crystalline structure of the phenazine overlayer physisorbed on a graphite surface

The monolayer structure of 1,2-bis(4-pyridyl)ethylene physisorbed on a graphite surface

Halogen Bonding in Bicomponent Monolayers: Self-Assembly of a Homologous Series of Iodinated Perfluoroalkanes with Bipyridine

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