Cost-Effective Force Field Tailored for Solid-Phase Simulations of OLED Materials

Moral, Mónica; Son, Won‐Joon; Sancho‐García, Juan Carlos; Olivier, Yoann; Muccioli, Luca

doi:10.1021/acs.jctc.5b00164

Cited by 27 publications

(43 citation statements)

References 90 publications

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“…This small disagreement between simulated and experimental structure is normally acceptable and in line with previous reports for organic crystals. [59]…”

Section: Force Field Benchmarksmentioning

confidence: 99%

Structure and Charge Transport Properties of Cycloparaphenylene Monolayers on Graphite

Pérez-Guardiola

Pérez-Jiménez

Muccioli³

et al. 2019

Adv Materials Inter

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The synthesis of CPPs has been experimentally challenging due to the strain energy needed to close the ring. [7] Vögtle and co-workers [8,9] attempted to synthesize CPPs from macrocycles formed by arene and cyclohexane units to therefore reduce the strain energy of the system. However, the first synthesis of CPPs was afforded only by Jasti et al. [10] in 2008, followed by the first selective synthesis of CPPs by Itami and co-workers [11,12] using a modular approach to build [n]CPPs with n ⩾ 12. Other successfully strategies (Yamago et al. [13] ) use a square-shaped tetra platinum biphenyl complex as an intermediate to selectively synthesize the [8]CPP molecule. In the above mentioned works, it was possible to obtain CPPs in the milligram-scale, with Jasti and co-workers [6,14] producing the first gram-scale synthesis. The smallest CPP synthesized up to date is [5]CPP, [15] which shows the great success achieved so far in overcoming the strain energy.Concerning the supramolecular packing, the solid-state (3D) structure of CPPs has been characterized in several works by means of X-ray diffraction. [16,17] The molecules self-assemble in a herringbone (HB) pattern independently of their size, as it often happens for other π-conjugated systems. An exception is the [6]CPP case, for which three different polymorphs have been found up to date. The first solid-state characterization of [6]CPP revealed a tubular-like structure, [14] but a recent study revealed that the crystallographic structure might depend on the crystallization conditions, also finding a herringbone configuration a few kcal mol −1 more stable than the tubular one. [18] More recently, another polymorph of [6]CPP has been found when the crystallization is carried out by sublimation at 220 °C. In these conditions, no solvent molecules are occluded inside the [6]CPP cavity, and thus, a concave-convex structure appears (i.e., molecules tightly packed in a T-like shape minimizing the internal space inside the cavities). [19] These findings clearly reveal the subtle yet dominant effect of the weak intermolecular interactions driving the supra molecular self-assembly of these systems. Motivated by this, some of us investigated in a previous theoretical work the adsorption energies of [8]CPP on small carbon nanoflakes (circumcirmcumcoronene) and how these through-space weak forces can serve to immobilize the systems in energetically favored configuration. [20] In the present study, we wish to go a step further and employ a tailored force field and molecular dynamics (MD) simulations to predict the supramolecular structure of thin films of CPPs on graphite surfaces. The systematic exploration of the adsorption The nanoscale organization of cycloparaphenylene molecules when physisorbed on a graphite surface is theoretically investigated by means of atomistic molecular dynamics simulations employing a tailored and benchmarked force field. The landing of a single molecule is first considered, to progressively deposit more molecules to finally reach the full coverage...

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“…This small disagreement between simulated and experimental structure is normally acceptable and in line with previous reports for organic crystals. [59]…”

Section: Force Field Benchmarksmentioning

confidence: 99%

Structure and Charge Transport Properties of Cycloparaphenylene Monolayers on Graphite

Pérez-Guardiola

Pérez-Jiménez

Muccioli³

et al. 2019

Adv Materials Inter

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“…However, the organic functional materials we are focussing on here typically contain p conjugated systems with aromatic moieties that in our view are more closely represented by flat ellipsoidal objects rather than spheres, even though a spherical representation of the beads can be used. 29,30 Although using spherical basic units is simpler, its down side is that of an increased number of beads, as exemplified by the united atoms (UA) approach, 31,32 the CG model closest to full atomistic, where just the hydrogen atoms are eliminated, absorbing them in the closest heavy atom.…”

Section: Introductionmentioning

confidence: 99%

MOLC. A reversible coarse grained approach using anisotropic beads for the modelling of organic functional materials

Ricci

Roscioni

Querciagrossa

et al. 2019

Phys. Chem. Chem. Phys.

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“…Torsional potentials for the phenyl-vinyl and phenyl-CC ≡ N rotation and for all the dihedrals along the oxybutyl chain were calculated with relaxed scans at the B3LYP/6-311G* level and inserted in the force field (see Ref. [47] for the details of the procedure). Standard Lorentz-Berthelot mixing rules [contact distances σ ij = (σ i + σ j )/2, well widths ij = √ i j ] were employed for modeling Lennard-Jones (LJ) interaction between different atom types (e.g., for tip-surface interaction).…”

Section: Free-energy Calculationsmentioning

confidence: 99%

Molecular-scale shear response of the organic semiconductor β -DBDCS (100) surface

et al. 2017

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In this work we present friction-force microscopy (FFM) lattice-resolved images acquired on the (100) facet of the semiconductor organic oligomer (2Z,2 Z) − 3,3 -(1,4-phenylene)bis(2-(4-butoxyphenyl)acrylonitrile) (β-DBDCS) crystal in water at room temperature. Stick-slip contrast, lateral contact stiffness, and friction forces are found to depend strongly on the sliding direction due to the anisotropic packing of the molecular chains forming the crystal surface along the [010] and [001] directions. The anisotropy also causes the maximum value of the normal force applicable before wearing to increase by a factor of 3 when the scan is performed along the [001] direction on the (100) face. Altogether, our results contribute to achieving a better understanding of the molecular origin of friction anisotropy on soft crystalline surfaces, which has been often hypothesized but rarely investigated in the literature.

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Cost-Effective Force Field Tailored for Solid-Phase Simulations of OLED Materials

Cited by 27 publications

References 90 publications

Structure and Charge Transport Properties of Cycloparaphenylene Monolayers on Graphite

Structure and Charge Transport Properties of Cycloparaphenylene Monolayers on Graphite

MOLC. A reversible coarse grained approach using anisotropic beads for the modelling of organic functional materials

Molecular-scale shear response of the organic semiconductor β -DBDCS (100) surface

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