Polymorphism and the influence of crystal structure on the luminescence of the opto-electronic material 4,4′-bis(9-carbazolyl)biphenyl

Gleason, Cody J.; Cox, Jordan M.; Walton, Ian M.; Benedict, Jason B.

doi:10.1039/c4ce01056f

Cited by 16 publications

(15 citation statements)

References 29 publications

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“…This may be linked to the observations made by optical microscopy, where these crystals did not seem to be space filling during the early stages of crystallization. Comparing to literature scattering patterns, the dendritic crystals that grow from the T sub = 240 K glass can clearly be identified as the γ polymorph. Some of the residual differences between the observed and the predicted patterns are attributed the different temperatures at which our WAXS pattern was measured (295 K) and the single-crystal structure was solved (90 K).…”

Section: Resultsmentioning

confidence: 67%

“…The most striking feature of GC growth is that the rate of crystal growth can increase by several orders of magnitude as the temperature is lowered just a few K near Tg. Gleason et al 4 determined that CBP can crystallize from solvent into three possible polymorphs (α, β, γ), where the α and γ polymorphs consist of CBP molecules with a very similar molecular conformation but different crystal packing, while the CBP molecules adopt a more twisted conformation in the β polymorph 25 .…”

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confidence: 99%

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Glass Structure Controls Crystal Polymorph Selection in Vapor-Deposited Films of 4,4′-Bis(N-carbazolyl)-1,1′-biphenyl

Brande

Gujral

Huang

et al. 2018

Crystal Growth & Design

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Glasses of a common OLED host material, 4,4′-bis(N-carbazolyl)-1,1′-biphenyl or CBP, were prepared by vapor deposition at various substrate temperatures. Consistent with previous work, the substrate temperature during deposition controls the anisotropic structure of the glass. Crystal growth at the free surface of CBP was very fast and was eliminated by covering the free surface with a thin overlayer of vapor-deposited tris-(8-hydroxyquinoline) aluminum (Alq3). It was observed that vapor-deposited glasses of CBP with an overlayer crystallized into either the α or γ polymorph, depending on the glass structure. To our knowledge, this is the first demonstration that two glasses of the same organic compound, subjected to the same annealing conditions, grow crystals of different polymorphs. The α polymorph exhibited a fine-grained morphology, reminiscent of previous studies on glass-crystal (GC) growth, while for the γ polymorph exhibited dendritic growth. Crystals of both polymorphs grew rapidly below the glass transition temperature Tg in comparison to previously studied GC growth systems such as o-terphenyl. Surprisingly, Tg for CBP was found to be about 385 K, well above previously reported values.

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Section: Resultsmentioning

confidence: 67%

mentioning

confidence: 99%

Glass Structure Controls Crystal Polymorph Selection in Vapor-Deposited Films of 4,4′-Bis(N-carbazolyl)-1,1′-biphenyl

Brande

Gujral

Huang

et al. 2018

Crystal Growth & Design

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“…CBP-patterned samples (Figure 3a,b) also display the selective attachment of fibronectin and fibroblasts, although with lower selectivity than DBP. This is due to CBP's tendency to aggregate into polycrystals 38 on the PPX-HM surface. The loosely adhered aggregates may delaminate during polymer brush growth, leaving behind a rough surface, apparent in the atomic force microscope image in Figure 3c.…”

Section: Resultsmentioning

confidence: 99%

Printable Organic Electronic Materials for Precisely Positioned Cell Attachment

et al. 2021

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Over the past 3 decades, there has been a vast expansion of research in both tissue engineering and organic electronics. Although the two fields have interacted little, the materials and fabrication technologies which have accompanied the rise of organic electronics offer the potential for innovation and translation if appropriately adapted to pattern biological materials for tissue engineering. In this work, we use two organic electronic materials as adhesion points on a biocompatible poly(p-xylylene) surface. The organic electronic materials are precisely deposited via vacuum thermal evaporation and organic vapor jet printing, the proven, scalable processes used in the manufacture of organic electronic devices. The small molecular-weight organics prevent the subsequent growth of antifouling polyethylene glycol methacrylate polymer brushes that grow within the interstices between the molecular patches, rendering these background areas both protein and cell resistant. Last, fibronectin attaches to the molecular patches, allowing for the selective adhesion of fibroblasts. The process is simple, reproducible, and promotes a high yield of cell attachment to the targeted sites, demonstrating that biocompatible organic small-molecule materials can pattern cells at the microscale, utilizing techniques widely used in electronic device fabrication.

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“…Structural polymorphism of 2D self-assemblies at the solid/liquid or solid/gas interface has attracted increasing attention in recent years, owing to their potential applications in new material fields, such as OLEDs, , organic photovoltaic cells (OPVs), , and organic field effect transistors (OFETs). , Thus it requires us to gain deep insight into the underlying mechanism behind the formation of specific monolayer morphology to guide the design of optical devices with desirable performance. In general, the outcome of a self-assembled monolayer is determined by a delicate balance of noncovalent intermolecular interactions, including hydrogen bonding, , van der Waals force, , dipole–dipole interaction, , electrostatic force, − and so on.…”

Section: Introductionmentioning

confidence: 99%

Polymorphic Self-Assemblies of 2,7-Bis(decyloxy)-9-fluorenone at the Solid/Gas Interface: Role of C–H···O═C Hydrogen Bond

Miao

Zha

et al. 2017

J. Phys. Chem. C

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The self-assembly of 2,7-bis(decyloxy)-9-fluorenone on highly oriented pyrolytic graphite is investigated at the solid/gas interface by scanning tunneling microscopy, which allows us to determine the effect of its molecular structure on the formation of monolayer morphology. By varying the solution concentration in dichloromethane, seven types of supramolecular assemblies can be obtained. The concentration-dependent structural polymorphism is discussed in terms of thermodynamics. In particular, these different patterns are identified to be bound with weak intermolecular C(sp2)–H···OC hydrogen bonds. As discerned by its position in the fluorenone moiety, the C(sp2)–H group with larger chemical shift value and stronger acidity displays a higher priority when involving in the formation of a C(sp2)–H···O hydrogen bond. Owing to the high density of C(sp2)–H donors, various hydrogen-bonding configurations arise, further leading to the occurrence of structural polymorphism. Besides, intermolecular van der Waals interactions as well as the dipole–dipole interactions act as the complementary roles to stabilize the whole monolayer. The underlying mechanism is further confirmed by the density functional theory calculations.

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Polymorphism and the influence of crystal structure on the luminescence of the opto-electronic material 4,4′-bis(9-carbazolyl)biphenyl

Abstract: Single crystal structures, luminescent properties and electronic structure calculations of three polymorphs of the opto-electronic charge transport material 4,4′-bis(9-carbazolyl)biphenyl.

Cited by 16 publications

References 29 publications

Glass Structure Controls Crystal Polymorph Selection in Vapor-Deposited Films of 4,4′-Bis(N-carbazolyl)-1,1′-biphenyl

Glass Structure Controls Crystal Polymorph Selection in Vapor-Deposited Films of 4,4′-Bis(N-carbazolyl)-1,1′-biphenyl

Printable Organic Electronic Materials for Precisely Positioned Cell Attachment

Polymorphic Self-Assemblies of 2,7-Bis(decyloxy)-9-fluorenone at the Solid/Gas Interface: Role of C–H···O═C Hydrogen Bond

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