Quantitative analysis of intermolecular interactions in orthorhombic rubrene

Hathwar, Venkatesha R.; Sist, Mattia; Jørgensen, Mads Ry Vogel; Mamakhel, Aref; Wang, Xiaoping; Hoffmann, Christina; Sugimoto, Kunihisa; Overgaard, Jacob; Iversen, Bo B.

doi:10.1107/s2052252515012130

Cited by 224 publications

(137 citation statements)

References 88 publications

(93 reference statements)

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“…The high values of mobility are attributed to the crystal packing which has a herringbone motif with a high overlap of the π‐conjugated tetracene backbone . In the monoclinic and triclinic polymorphs, device performance is significantly reduced due to the absence of π‐stacking interactions in the monoclinic polymorph and the significant slippage of tetracene backbones relative to one another in the triclinic polymorph . A comparative study on single crystals of the Cmca orthorhombic form and the triclinic form, both grown from solution, revealed that the orthorhombic form exhibited hole mobilities of up to 1.6 cm 2 V −1 s −1 , while the triclinic form showed lower charge carrier mobilities of only 0.1 cm 2 V −1 s −1 .…”

Section: Experimentally Observed Sipsmentioning

confidence: 99%

Substrate‐Induced and Thin‐Film Phases: Polymorphism of Organic Materials on Surfaces

Jones

Chattopadhyay

Geerts

et al. 2016

Adv Funct Materials

228

280

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2233wileyonlinelibrary.com to that of the bulk liquid; [ 7 ] order typically exists over a few molecular layers before rapidly decaying to bulk behavior as the distance from the wall increases. [ 8 ] Similar ordering effects can also be observed in the quasiliquids which form on the surface of many solids due to surface melting (also known as premelting): [ 9,10 ] the existence of a liquid-like layer a few molecules thick on the surface of a solid below the melting point of the bulk material. [ 11 ] The structure within this layer is also found to be different to that of the bulk isotropic liquid, [ 12 ] highlighting the ordering occurring at the interface. A converse effect, surface freezing, is also observed in some liquids (primarily n -alkanes with 16 ≤ n ≤ 50), where a solid monolayer may exist at an interface up to ≈30 °C above the bulk melting point while the rest of the compound is molten. [13][14][15] Such phase behavior is strongly dependent on molecular shape and has only been observed for chain molecules, which then form layers similar to self-assembled monolayers (SAMs) at the interface with the liquid bulk. [ 16 ] Further examples of molecular ordering at interfaces can be seen in materials which display liquid crystal (LC) phases, a phase behavior also dependent on molecular shape and generally observed for molecules with a highly anisotropic shape (e.g., rod-like, disc-like or bowl-like molecules). [ 17 ] LCs have properties of both solids and liquids and display long range order which may be orientational and/or positional; various types of LC phases (mesophases) are possible and normally exist only over a certain temperature range (i.e., they are thermotropic); a further property of LCs is that they generally reach thermodynamic equilibrium in the bulk and at interfaces as a result of their short relaxation time. Nematic (N) phases of calamitic LCs (rod-like molecules with cylindrical symmetry) have no positional order but an orientational order which can be described by a unit vector, n , known as the director, which represents the preferred molecular orientation ( Figure 1 , left). A scalar order parameter can also be defi ned which is related to the average angle the long molecular axes make to the director, n .Increased order is seen in smetic phases (Sm) which have both orientational and positional order; for example in a smetic A phase (SmA) molecules form layers (positional ordering of the molecular mass centers) which are oriented normal to the plane of the layers (orientational order), while smetic C phases (SmC) form layers where molecules are oriented with the long molecular axes tilted at an angle to the molecular layer normal However, the factors that drive such a process are not clearly understood or studied in depth. In this feature article, we review the current state of understanding concerning SIPs, giving examples of systems where SIPs have been observed, discussing their origins, and which questions remain to be answered. The role of the substrate in controlling the growth a...

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Section: Experimentally Observed Sipsmentioning

confidence: 99%

Substrate‐Induced and Thin‐Film Phases: Polymorphism of Organic Materials on Surfaces

Jones

Chattopadhyay

Geerts

et al. 2016

Adv Funct Materials

228

280

View full text Add to dashboard Cite

show abstract

“…The Hirshfeld surface analysis confirms the importance of H-atom contacts in establishing the packing. The large number of HÁ Á ÁH, HÁ Á ÁO/OÁ Á ÁH and HÁ Á ÁC/CÁ Á ÁH interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al, 2015).…”

Section: Figurementioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-(1,3-benzothiazol-2-yl)-3-(2-hydroxyethyl)imidazolidin-2-one

Srhir¹,

Sebbar

Hökelek

et al. 2020

Acta Cryst E

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In the title molecule, C12H13N3O2S, the benzothiazine moiety is slightly non-planar, with the imidazolidine portion twisted only a few degrees out of the mean plane of the former. In the crystal, a layer structure parallel to the bc plane is formed by a combination of O—HHydethy...NThz hydrogen bonds and weak C—HImdz...OImdz and C—HBnz...OImdz (Hydethy = hydroxyethyl, Thz = thiazole, Imdz = imidazolidine and Bnz = benzene) interactions, together with C—HImdz...π(ring) and head-to-tail slipped π-stacking [centroid-to-centroid distances = 3.6507 (7) and 3.6866 (7) Å] interactions between thiazole rings. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (47.0%), H...O/O...H (16.9%), H...C/C...H (8.0%) and H...S/S...H (7.6%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C—H...N and C—H...O hydrogen-bond energies are 68.5 (for O—HHydethy...NThz), 60.1 (for C—HBnz...OImdz) and 41.8 kJ mol−1 (for C—HImdz...OImdz). Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state.

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“…All of the contributions to the Hirshfeld surface are given in Table 3. The large number of HÁ Á ÁH, CÁ Á ÁH/HÁ Á ÁC and HÁ Á ÁBr/BrÁ Á ÁH interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al, 2015).…”

Section: Figurementioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (E)-3-(benzylideneamino)-5-phenylthiazolidin-2-iminium bromide

et al. 2020

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The central thiazolidine ring of the title salt, C16H16N3S+·Br−, adopts an envelope conformation, with the C atom bearing the phenyl ring as the flap atom. In the crystal, the cations and anions are linked by N—H...Br hydrogen bonds, forming chains parallel to the b-axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (46.4%), C...H/H...C (18.6%) and H...Br/Br...H (17.5%) interactions.

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Quantitative analysis of intermolecular interactions in orthorhombic rubrene

Cited by 224 publications

References 88 publications

Substrate‐Induced and Thin‐Film Phases: Polymorphism of Organic Materials on Surfaces

Substrate‐Induced and Thin‐Film Phases: Polymorphism of Organic Materials on Surfaces

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-(1,3-benzothiazol-2-yl)-3-(2-hydroxyethyl)imidazolidin-2-one

Crystal structure and Hirshfeld surface analysis of (E)-3-(benzylideneamino)-5-phenylthiazolidin-2-iminium bromide

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