The crystalline state of rubrene materials: intermolecular recognition, isomorphism, polymorphism, and periodic bond-chain analysis of morphologies

Moret, Massimo; Gavezzotti, Angelo

doi:10.1039/d2nj00861k

Cited by 6 publications

(7 citation statements)

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“…While the triclinic form retains the planar backbone, it packs in a brick-like arrangement, which has been shown with rubrene to have significantly reduced charge mobility (Matsukawa et al, 2010). This is a similar case to the NO 2 -substituted rubrene derivative [5,11-bis(4-nitrophenyl)-6,12-biphenyltetracene] in which the monoclinic form was discovered (Uttiya et al, 2014), with the triclinic reported later (Moret & Gavezzotti, 2022).…”

Section: Database Surveymentioning

confidence: 68%

Two new cases of polymorphism in diagonally substituted rubrene derivatives

Clapham

Douglas

2023

Acta Cryst E

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The crystal structures of two rubrene derivatives, 5,11-diphenyl-6,12-bis[4-(trifluoromethyl)phenyl]tetracene, C44H26F6, and 5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene, C50H44, are presented. Each are substituted on diagonal (5/11) phenyl rings. Each derivative has one polymorph reported previously. A discussion of the differences between each derivative and its previously reported polymorph is provided. The triclinic packing of the CF3-substituted structure is similar to the packing of the parent rubrene's triclinic polymorph. In the tert-butyl-substituted structure, a planar tetracene core formed, which has been hypothesized but never published. Crystallization conditions are provided as they differ from previous reports.

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Section: Database Surveymentioning

confidence: 68%

Two new cases of polymorphism in diagonally substituted rubrene derivatives

Clapham

Douglas

2023

Acta Cryst E

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“…10 The formations of Herringbone structures are guided by solvent, 11 host−guest interactions, 12 effect of substituents, 13 and stimuli. 14 Stacking among the phenyl rings occur in several ways such as edge-to-face, face-to-face, or oblique types, as illustrated in Figure 1a. 15 It may be seen that the face-to-face parallel molecules either having eclipsed (Figure 1a (iii) or partly eclipsed (Figure 1a (vi)) geometries may be further arranged in different ways at translated positions in the case of eclipsed pairs, or as in a uni-directional manner (Figure 1a (vii)) or in bi-directions (Figure 1a (viii)).…”

Section: Introductionmentioning

confidence: 99%

π-Stacking among the Anthracenyl Groups of a Copper Complex Resulted in Doubling of Unit Cell Volume To Provide New Polymorphs

Singh

Baruah

2023

ACS Omega

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T w o p o l y m o r p h s o f t h e 9 -N -( 3imidazolylpropylamino)methylanthracene (Hanthraimmida) containing hydrated copper(II)-2,6-pyridinedicarboxylate complex are reported. The two polymorphs have either lamellar or Herringbone arrangements of π-stacks among the anthracenyl groups of organocation. The difference between the two polymorphs originated from having face-to-face stacking arrangements between the two anthracenyl groups of the symmetry independent cations within the unit cell in one of the polymorphs. The π-stacked anthracenyl groups in consecutive layers of the polymorphs are oriented in one direction in the polymorph designated as P1, whereas the polymorph designated as P2 has such orientations in opposite directions. The unit cell volume of the polymorph P2 (Z = 4) has approximately twice the volume of the polymorph P1 (Z = 2); it happend due to coalescence of two unit cells of P1 in the ab-crystallographic plane. A mixed methanol/water solvate of the copper complex is also reported. It has a channel-like arrangement of the cations; has the anions and the solvents within the cation embraced channel-like enclosures. This complex is unstable, once taken out from the methanol solvent, it transforms in real time to P2 by replacements of the methanol molecules by water molecules.

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“…The resulting energy/structure landscape has intrinsic valuable information even if the holy Grail of exact crystal structure prediction is not attained. Having a plausible crystal structure, one can proceed to simulate surface properties and crystal morphologies, [16] important for stability and bioavailability, or to derive lattice vibrations and other thermodynamic, spectroscopic and heat conduction properties, important for materials science, by dedicated and extremely efficient downstream software [17] . These properties may change in different polymorphs, but any plausible structure can give an order‐of‐magnitude estimate and a preliminary idea of what one can expect from a given material.…”

Section: Introductionmentioning

confidence: 99%

Crystallography without Crystals: A Structural Study of Fakein

Gavezzotti

2022

Helvetica Chimica Acta

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Dedicated to the memory of Jack D. Dunitz Software from the MiCMoS Molecular Simulation platform (sites.unimi.it/xtal_chem_group/) and from the CryGen set of programs (www.angelogavezzotti.it) is used to prepare a molecular structure from a line formula for a non-existent molecule, dubbed 'fakein'. Possible crystal structures are generated in chiral space groups P2 1 and P2 1 2 1 2 1 , and for racemate in space groups P1À and P2 1 /c. Lattice energies and crystal densities are in line with experimental values for organic molecules. Chiral crystals are less stable, and may not easily form hydrogen bonds, while bulk crystal stabilization is provided mostly by polarization-dispersion. Hydrogen bonding and crystal packing are discussed in terms of molecular pairing modes. Links to possible experiments and to absolute crystal structure prediction are outlined, but the main aim here is to demonstrate that relevant solid-state information can be derived if that goal is not achieved, actually even if the real substance is not available.

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The crystalline state of rubrene materials: intermolecular recognition, isomorphism, polymorphism, and periodic bond-chain analysis of morphologies

Abstract: A survey of all crystal structures of rubrene materials in the Cambridge Structural Database is presented. Although the chemical substitution landscape is wide, hydrogen bonding functionalities are absent. Recognition motifs...

Cited by 6 publications

References 50 publications

Two new cases of polymorphism in diagonally substituted rubrene derivatives

Two new cases of polymorphism in diagonally substituted rubrene derivatives

π-Stacking among the Anthracenyl Groups of a Copper Complex Resulted in Doubling of Unit Cell Volume To Provide New Polymorphs

Crystallography without Crystals: A Structural Study of Fakein

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