Giant Polycyclic Aromatic Hydrocarbons

Müller, Markus; Kübel, Christian; Müllen, Kläus

doi:10.1002/(sici)1521-3765(19981102)4:11<2099::aid-chem2099>3.0.co;2-t

Cited by 254 publications

(168 citation statements)

References 35 publications

Supporting

Mentioning

160

Contrasting

Unclassified

Order By: Relevance

“…Hexabenzocorene. Hexabenzocoronene (HBC), C 42 H 18 , has recently received much attention because it displays a wide range of interesting structural and electrical properties (48)(49)(50)(51). It is a discotic molecule made of 13 fused benzene rings and it possesses D 6h symmetry; HBC molecules substituted by saturated chains can be arranged into one-dimensional stacks in liquid crystalline phases, for which remarkable room temperature mobilities approaching 1 cm 2 ͞Vs have been reported recently (52).…”

Section: Resultsmentioning

confidence: 99%

Organic semiconductors: A theoretical characterization of the basic parameters governing charge transport

Brédas

Calbert

Filho

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

1,210

993

View full text Add to dashboard Cite

Organic semiconductors based on -conjugated oligomers and polymers constitute the active elements in new generations of plastic (opto)electronic devices. The performance of these devices depends largely on the efficiency of the charge-transport processes; at the microscopic level, one of the major parameters governing the transport properties is the amplitude of the electronic transfer integrals between adjacent oligomer or polymer chains. Here, quantum-chemical calculations are performed on model systems to address the way transfer integrals between adjacent chains are affected by the nature and relative positions of the interacting units. Compounds under investigation include oligothienylenes, hexabenzocoronene, oligoacenes, and perylene. It is shown that the amplitude of the transfer integrals is extremely sensitive to the molecular packing. Interestingly, in contrast to conventional wisdom, specific arrangements can lead to electron mobilities that are larger than hole mobilities, which is, for instance, the case of perylene. O rganic -conjugated materials offer remarkable potential as active elements in (opto)electronic devices that exploit their semiconducting properties, such as field-effect transistors (FETs; refs. 1-8), light-emitting diodes (LEDs; refs. 9-13), or photovoltaic and solar cells (14-17). Such devices are expected to be ultimately incorporated, for instance, into all-plastic integrated circuits for low-end and cheap electronics (7,8,18) and all-plastic light-emitting displays, where each pixel consists of an organic LED driven by an organic FET (19,20). In all of these applications, the efficiency of charge transport within the organic layer(s) plays a key role. In light-emitting diodes, it is desirable that the injected holes and electrons have large and similar mobilities to prevent electroluminescence quenching that can occur when charges recombine close to a metallic interface (21); high-charge mobilities favor recombination processes in the bulk (where charges can be confined further by means of organic-organic interfaces; ref. 22). In solar cells, the charges created upon photoexcitation of the active material have to be transported efficiently to be collected at the metallic contacts and stored under the form of electrical energy. Another challenge is to develop materials displaying high electron and hole mobilities in field-effect architectures to design complex organic circuits.The charge-transport properties critically depend on the degree of ordering of the chains in the solid state as well as on the density of chemical and͞or structural defects (23)(24)(25). This dependence explains why, over the last decades, the experimental characterization of the transport properties in organic thin films or crystals has led to results that vary with sample quality. Recently, the synthesis of ultra-pure single crystals of organic semiconductors such as oligoacenes has allowed Batlogg and coworkers (28) to demonstrate remarkable features that in many instances had been thought to be restricte...

show abstract

Section: Resultsmentioning

confidence: 99%

Organic semiconductors: A theoretical characterization of the basic parameters governing charge transport

Brédas

Calbert

Filho

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

1,210

993

View full text Add to dashboard Cite

show abstract

“…1,2 The size and the shape of the cores can be varied, as well as the length and the structure of the side chains, which allows the control of functional properties of these mesophases. [3][4][5] Liquid-crystalline properties such as fluidity are of help to process these compounds and even to develop self-healing materials.…”

Section: Introductionmentioning

confidence: 99%

Coarse-grained interaction potentials for polyaromatic hydrocarbons

Lilienfeld

Andrienko

2006

The Journal of Chemical Physics

View full text Add to dashboard Cite

Using Kohn-Sham ͑KS͒ density-functional theory, we have studied the interaction between various polyaromatic hydrocarbon molecules. The systems range from monocyclic benzene up to hexabenzocoronene ͑hbc͒. For several conventional exchange-correlation functionals total potential-energy curves of interaction of the -stacking hbc dimer are reported. It is found that all pure local density or generalized gradient approximated functionals yield qualitatively incorrect predictions regarding structure and interaction. Inclusion of a nonlocal, atom-centered correction to the KS Hamiltonian enables quantitative predictions. The computed potential-energy surfaces of interaction yield parameters for a coarse-grained potential, which can be employed to study discotic liquid-crystalline mesophases of derived polyaromatic macromolecules.

show abstract

“…This would indicate that a more sophisticated procedure may occur in the proximity of certain stars, where there are interstellar emission bands which indicate high temperatures. However, certain doubts exist concerning the predominance of this species, in comparison to the PAHs which have been regarded as molecularly defined models of graphite [14][15][16][17][18], so that coronene and ovalene as well as other large molecules of this kind provide apt models for the present comparison. Intrinsic aromaticity is an important aspect to be considered in this comparison, as it is thought to represent a stabilizing factor.…”

Section: Introductionmentioning

confidence: 99%

Aromaticity under star dust conditions

Salcedo¹,

Fomina²

2011

Struct Chem

View full text Add to dashboard Cite

Astronomical observations have revealed diffuse interstellar bands ranging from blue in the visible spectrum to the near IR. It has been suggested that these bands exist, owing to the presence of polyaromatic hydrocarbons or fullerene in the vicinity of certain stars, and constitute residual material from stellar explosions. The intention here is to study the relative stability of these species, when exposed to extreme conditions. The aromaticity of polycarbon molecules is an important aspect of this explanation.

show abstract

Giant Polycyclic Aromatic Hydrocarbons

Cited by 254 publications

References 35 publications

Organic semiconductors: A theoretical characterization of the basic parameters governing charge transport

Organic semiconductors: A theoretical characterization of the basic parameters governing charge transport

Coarse-grained interaction potentials for polyaromatic hydrocarbons

Aromaticity under star dust conditions

Contact Info

Product

Resources

About