Diindenoperylene

Last updated
Diindenoperylene
Diindenoperylene.svg
Diindenoperylene-3D-balls.png
Names
Preferred IUPAC name
Diindeno[1,2,3-cd:1′,2′,3′-lm]perylene
Other names
Periflanthen; Periflanthene
Identifiers
3D model (JSmol)
AbbreviationsDIP
ChemSpider
ECHA InfoCard 100.005.343 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C32H16/c1-2-6-18-17(5-1)21-9-13-25-27-15-11-23-19-7-3-4-8-20(19)24-12-16-28(32(27)30(23)24)26-14-10-22(18)29(21)31(25)26/h1-16H X mark.svgN
    Key: BKMIWBZIQAAZBD-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C32H16/c1-2-6-18-17(5-1)21-9-13-25-27-15-11-23-19-7-3-4-8-20(19)24-12-16-28(32(27)30(23)24)26-14-10-22(18)29(21)31(25)26/h1-16H
    Key: BKMIWBZIQAAZBD-UHFFFAOYAB
  • C1=CC2=C3C=CC4=C5C=CC6=C7C=CC=CC7=C8C6=C5C(=C9C4=C3C(=C2C=C1)C=C9)C=C8
Properties
C32H16
Molar mass 400.480 g·mol−1
AppearanceOrange solid
Boiling point >330 °C (sublimation)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Diindenoperylene (DIP) is an organic semiconductor which receives attention because of its potential application in optoelectronics (solar cells, OLEDs) and electronics (RFID tags). DIP is a planar perylene derivative with two indeno-groups attached to opposite sides of the perylene core. Its chemical formula is C32H16, the full chemical name is diindeno[1,2,3-cd:1',2',3'-lm]perylene. Its chemical synthesis has been described. [1] [2]

Properties and uses

The molecular weight is 400.48 g/mol, the dimensions of the molecule in its plane are ~18.4×7 Å. [3] and its sublimation temperature is above 330 °C. [4] It is non-polar and therefore only slightly soluble, for example in acetone.

DIP is a red dye [5] and has been used as active material for optical recording. [6] Because of its ‘perylene-type’ optical emission in the visible spectrum, it has also been used in organic light emitting diodes. [7] Organic field effect transistors of DIP have been studied. [8] The charge carrier mobility achieved was up to 0.1 cm2/(V·s) for thin film transistors with silicon dioxide as gate dielectric, making DIP a good candidate for further optimisation. [9]

The structure of bulk DIP crystals has recently been studied by Pflaum et al., who found two distinct phases at room temperature and at temperatures above 160 °C. In thin films for growth ‘near equilibrium’ (at substrate temperature of about 130 °C) by organic molecular beam deposition (OMBD), DIP has been shown to order very well. [2] [10] The structure of thin DIP films has been characterized ‘post-growth’, [2] [11] [12] [13] with structures differing from the room-temperature bulk structure. These thin-film structures depend on the substrate used, and also on the substrate temperature during growth. [10]

Related Research Articles

The Schön scandal concerns German physicist Jan Hendrik Schön who briefly rose to prominence after a series of apparent breakthroughs with semiconductors that were later discovered to be fraudulent. Before he was exposed, Schön had received the Otto-Klung-Weberbank Prize for Physics and the Braunschweig Prize in 2001, as well as the Outstanding Young Investigator Award of the Materials Research Society in 2002, all of which were later rescinded.

<span class="mw-page-title-main">Polariton</span> Quasiparticles arising from EM wave coupling

In physics, polaritons are quasiparticles resulting from strong coupling of electromagnetic waves with an electric or magnetic dipole-carrying excitation. They are an expression of the common quantum phenomenon known as level repulsion, also known as the avoided crossing principle. Polaritons describe the crossing of the dispersion of light with any interacting resonance. To this extent polaritons can also be thought of as the new normal modes of a given material or structure arising from the strong coupling of the bare modes, which are the photon and the dipolar oscillation. The polariton is a bosonic quasiparticle, and should not be confused with the polaron, which is an electron plus an attached phonon cloud.

<span class="mw-page-title-main">Molecular-beam epitaxy</span> Crystal growth process

Molecular-beam epitaxy (MBE) is an epitaxy method for thin-film deposition of single crystals. MBE is widely used in the manufacture of semiconductor devices, including transistors, and it is considered one of the fundamental tools for the development of nanotechnologies. MBE is used to fabricate diodes and MOSFETs at microwave frequencies, and to manufacture the lasers used to read optical discs.

<span class="mw-page-title-main">Strontium titanate</span> Chemical compound

Strontium titanate is an oxide of strontium and titanium with the chemical formula SrTiO3. At room temperature, it is a centrosymmetric paraelectric material with a perovskite structure. At low temperatures it approaches a ferroelectric phase transition with a very large dielectric constant ~104 but remains paraelectric down to the lowest temperatures measured as a result of quantum fluctuations, making it a quantum paraelectric. It was long thought to be a wholly artificial material, until 1982 when its natural counterpart—discovered in Siberia and named tausonite—was recognised by the IMA. Tausonite remains an extremely rare mineral in nature, occurring as very tiny crystals. Its most important application has been in its synthesized form wherein it is occasionally encountered as a diamond simulant, in precision optics, in varistors, and in advanced ceramics.

<span class="mw-page-title-main">Polaron</span> Quasiparticle in condensed matter physics

A polaron is a quasiparticle used in condensed matter physics to understand the interactions between electrons and atoms in a solid material. The polaron concept was proposed by Lev Landau in 1933 and Solomon Pekar in 1946 to describe an electron moving in a dielectric crystal where the atoms displace from their equilibrium positions to effectively screen the charge of an electron, known as a phonon cloud. This lowers the electron mobility and increases the electron's effective mass.

Organic semiconductors are solids whose building blocks are pi-bonded molecules or polymers made up by carbon and hydrogen atoms and – at times – heteroatoms such as nitrogen, sulfur and oxygen. They exist in the form of molecular crystals or amorphous thin films. In general, they are electrical insulators, but become semiconducting when charges are either injected from appropriate electrodes, upon doping or by photoexcitation.

<span class="mw-page-title-main">Organic field-effect transistor</span> Type of field-effect transistor

An organic field-effect transistor (OFET) is a field-effect transistor using an organic semiconductor in its channel. OFETs can be prepared either by vacuum evaporation of small molecules, by solution-casting of polymers or small molecules, or by mechanical transfer of a peeled single-crystalline organic layer onto a substrate. These devices have been developed to realize low-cost, large-area electronic products and biodegradable electronics. OFETs have been fabricated with various device geometries. The most commonly used device geometry is bottom gate with top drain and source electrodes, because this geometry is similar to the thin-film silicon transistor (TFT) using thermally grown SiO2 as gate dielectric. Organic polymers, such as poly(methyl-methacrylate) (PMMA), can also be used as dielectric. One of the benefits of OFETs, especially compared with inorganic TFTs, is their unprecedented physical flexibility, which leads to biocompatible applications, for instance in the future health care industry of personalized biomedicines and bioelectronics.

Magnetic semiconductors are semiconductor materials that exhibit both ferromagnetism and useful semiconductor properties. If implemented in devices, these materials could provide a new type of control of conduction. Whereas traditional electronics are based on control of charge carriers, practical magnetic semiconductors would also allow control of quantum spin state. This would theoretically provide near-total spin polarization, which is an important property for spintronics applications, e.g. spin transistors.

<span class="mw-page-title-main">Bismuth telluride</span> Chemical compound

Bismuth telluride is a gray powder that is a compound of bismuth and tellurium also known as bismuth(III) telluride. It is a semiconductor, which, when alloyed with antimony or selenium, is an efficient thermoelectric material for refrigeration or portable power generation. Bi2Te3 is a topological insulator, and thus exhibits thickness-dependent physical properties.

<span class="mw-page-title-main">Boron arsenide</span> Chemical compound

Boron arsenide is a chemical compound involving boron and arsenic, usually with a chemical formula BAs. Other boron arsenide compounds are known, such as the subarsenide B12As2. Chemical synthesis of cubic BAs is very challenging and its single crystal forms usually have defects.

<span class="mw-page-title-main">Germanium telluride</span> Chemical compound

Germanium telluride (GeTe) is a chemical compound of germanium and tellurium and is a component of chalcogenide glasses. It shows semimetallic conduction and ferroelectric behaviour.

Gallium manganese arsenide, chemical formula (Ga,Mn)As is a magnetic semiconductor. It is based on the world's second most commonly used semiconductor, gallium arsenide,, and readily compatible with existing semiconductor technologies. Differently from other dilute magnetic semiconductors, such as the majority of those based on II-VI semiconductors, it is not paramagnetic but ferromagnetic, and hence exhibits hysteretic magnetization behavior. This memory effect is of importance for the creation of persistent devices. In (Ga,Mn)As, the manganese atoms provide a magnetic moment, and each also acts as an acceptor, making it a p-type material. The presence of carriers allows the material to be used for spin-polarized currents. In contrast, many other ferromagnetic magnetic semiconductors are strongly insulating and so do not possess free carriers. (Ga,Mn)As is therefore a candidate as a spintronic material.

<span class="mw-page-title-main">Gallium(II) selenide</span> Chemical compound

Gallium(II) selenide (GaSe) is a chemical compound. It has a hexagonal layer structure, similar to that of GaS. It is a photoconductor, a second harmonic generation crystal in nonlinear optics, and has been used as a far-infrared conversion material at 14–31 THz and above.

<span class="mw-page-title-main">Topological insulator</span> State of matter with insulating bulk but conductive boundary

A topological insulator is a material whose interior behaves as an electrical insulator while its surface behaves as an electrical conductor, meaning that electrons can only move along the surface of the material.

A trion is a localized excitation which consists of three charged particles. A negative trion consists of two electrons and one hole and a positive trion consists of two holes and one electron. The trion itself is a quasiparticle and is somewhat similar to an exciton, which is a complex of one electron and one hole. The trion has a ground singlet state (spin S = 1/2) and an excited triplet state (S = 3/2). Here singlet and triplet degeneracies originate not from the whole system but from the two identical particles in it. The half-integer spin value distinguishes trions from excitons in many phenomena; for example, energy states of trions, but not excitons, are split in an applied magnetic field. Trion states were predicted theoretically in 1958; they were observed experimentally in 1993 in CdTe/Cd1−xZnxTe quantum wells, and later in various other optically excited semiconductor structures. There are experimental proofs of their existence in nanotubes supported by theoretical studies. Despite numerous reports of experimental trion observations in different semiconductor heterostructures, there are serious concerns on the exact physical nature of the detected complexes. The originally foreseen 'true' trion particle has a delocalized wavefunction (at least at the scales of several Bohr radii) while recent studies reveal significant binding from charged impurities in real semiconductor quantum wells.

<span class="mw-page-title-main">Silicene</span> Two-dimensional allotrope of silicon

Silicene is a two-dimensional allotrope of silicon, with a hexagonal honeycomb structure similar to that of graphene. Contrary to graphene, silicene is not flat, but has a periodically buckled topology; the coupling between layers in silicene is much stronger than in multilayered graphene; and the oxidized form of silicene, 2D silica, has a very different chemical structure from graphene oxide.

<span class="mw-page-title-main">Transition metal dichalcogenide monolayers</span> Thin semiconductors

Transition-metal dichalcogenide (TMD or TMDC) monolayers are atomically thin semiconductors of the type MX2, with M a transition-metal atom (Mo, W, etc.) and X a chalcogen atom (S, Se, or Te). One layer of M atoms is sandwiched between two layers of X atoms. They are part of the large family of so-called 2D materials, named so to emphasize their extraordinary thinness. For example, a MoS2 monolayer is only 6.5 Å thick. The key feature of these materials is the interaction of large atoms in the 2D structure as compared with first-row transition-metal dichalcogenides, e.g., WTe2 exhibits anomalous giant magnetoresistance and superconductivity.

<span class="mw-page-title-main">Amorphous silicon</span> Non-crystalline silicon

Amorphous silicon (a-Si) is the non-crystalline form of silicon used for solar cells and thin-film transistors in LCDs.

<span class="mw-page-title-main">Surface differential reflectivity</span> Spectroscopic technique

Surface differential reflectivity (SDR) or differential reflectance spectroscopy (DRS) is a spectroscopic technique that measures and compares the reflectivity of a sample in two different physical conditions. The result is presented in terms of ΔR/R, which is defined as follow:

References

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  2. 1 2 3 E. Clar, Polycyclic hydrocarbons (Academic Press, London, New York, 1964), p. 2
  3. Dürr, A. C.; Schreiber, F.; Münch, M.; Karl, N.; Krause, B.; Kruppa, V.; Dosch, H. (2002). "High structural order in thin films of the organic semiconductor diindenoperylene". Applied Physics Letters. 81 (12): 2276. Bibcode:2002ApPhL..81.2276D. doi:10.1063/1.1508436.
  4. A. C. Dürr, Ph.D. thesis, Universität Stuttgart (2002)
  5. Heilig, M; Domhan, M; Port, H (2004). "Optical properties and morphology of thin diindenoperylene films". Journal of Luminescence . 110 (4): 290. Bibcode:2004JLum..110..290H. doi:10.1016/j.jlumin.2004.08.023.
  6. H. E. Simmons. (1987)
  7. H. Antoniadis, A. J. Bard. (Hewlett-Packard Company & The Board of Regents of The University of Palo Alto, CA, 1997)
  8. M. Münch, Ph.D. thesis, Universität Stuttgart (2001)
  9. N. Karl, in Organic Electronic Materials R. Farchioni, G. Grosso, Eds. (Springer, Berlin, 2001), vol. II, ISBN   3-540-66721-0 pp. 283 ff.
  10. 1 2 Kowarik, S.; Gerlach, A.; Sellner, S.; Schreiber, F.; Cavalcanti, L.; Konovalov, O. (2006). "Real-Time Observation of Structural and Orientational Transitions during Growth of Organic Thin Films". Physical Review Letters. 96 (12): 125504. Bibcode:2006PhRvL..96l5504K. doi:10.1103/PhysRevLett.96.125504. PMID   16605925. S2CID   1223144.
  11. Dürr, A.; Schreiber, F.; Ritley, K.; Kruppa, V.; Krug, J.; Dosch, H.; Struth, B. (2003). "Rapid Roughening in Thin Film Growth of an Organic Semiconductor (Diindenoperylene)". Physical Review Letters. 90 (1): 016104. Bibcode:2003PhRvL..90a6104D. doi:10.1103/PhysRevLett.90.016104. PMID   12570630.
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  13. Hoshino, A; Isoda, Seiji; Kobayashi, Takashi (1991). "Epitaxial growth of organic crystals on organic substrates — polynuclear aromatic hydrocarbons". Journal of Crystal Growth. 115 (1–4): 826–830. Bibcode:1991JCrGr.115..826H. doi:10.1016/0022-0248(91)90854-X.