Tetracene

Last updated
Tetracene
Tetracene 200.svg
Tetracene molecule spacefill.png
Tetracene crystals.jpg
Names
Preferred IUPAC name
Tetracene [1]
Other names
Naphthacene
Benz[b]anthracene
2,3-Benzanthracene
Tetracyclo[8.8.0.03,8.012,17]octadeca-1,3,5,7,9,11,13,15,17-nonaene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.945 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C18H12/c1-2-6-14-10-18-12-16-8-4-3-7-15(16)11-17(18)9-13(14)5-1/h1-12H Yes check.svgY
    Key: IFLREYGFSNHWGE-UHFFFAOYSA-N Yes check.svgY
  • c1c2cc3cc4ccccc4cc3cc2ccc1
Properties
C18H12
Molar mass 228.29 g/mol
AppearanceYellow to orange solid
Melting point 357 °C (675 °F; 630 K)
Boiling point 436.7 °C (818.1 °F; 709.8 K)
Insoluble
-168.0·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Tetracene, also called naphthacene, is a polycyclic aromatic hydrocarbon. It has the appearance of a pale orange powder. Tetracene is the four-ringed member of the series of acenes.

Contents

Tetracene is a molecular organic semiconductor, used in organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). Tetracene can be used as a gain medium in dye lasers as a sensitiser in chemoluminescence. Napthacene is the main component of the tetracycline class of antibiotics.

History

German physicist Jan Hendrik Schön claimed to have developed an electrically pumped laser based on tetracene during his time at Bell Labs (1997–2002). However, his results could not be reproduced, and this is considered to be a scientific fraud. [2]

In May 2007, Japanese researchers from Tohoku University and Osaka University reported an ambipolar light-emitting transistor made of a single tetracene crystal. [3] Ambipolar means that the electric charge is transported by both positively charged holes and negatively charged electrons.

In 2024, it was used to produce lower-energy excitations in solar cells in a process known as singlet fission. An interface layer between tetracene and silicon transfers them into the silicon layer, where most of their energy can be converted into electricity. [4]

See also

Notes

Related Research Articles

<span class="mw-page-title-main">Organic electronics</span> Field of materials science

Organic electronics is a field of materials science concerning the design, synthesis, characterization, and application of organic molecules or polymers that show desirable electronic properties such as conductivity. Unlike conventional inorganic conductors and semiconductors, organic electronic materials are constructed from organic (carbon-based) molecules or polymers using synthetic strategies developed in the context of organic chemistry and polymer chemistry.

A semiconductor is a material that has an electrical conductivity value falling between that of a conductor, such as copper, and an insulator, such as glass. Its resistivity generally falls as its temperature rises; metals behave in the opposite way. In many cases their conducting properties may be altered in useful ways by introducing impurities ("doping") into the crystal structure. When two differently doped regions exist in the same crystal, a semiconductor junction is created. The behavior of charge carriers, which include electrons, ions, and electron holes, at these junctions is the basis of diodes, transistors, and most modern electronics. Some examples of semiconductors are silicon, germanium, gallium arsenide, and elements near the so-called "metalloid staircase" on the periodic table. After silicon, gallium arsenide is the second-most common semiconductor and is used in laser diodes, solar cells, microwave-frequency integrated circuits, and others. Silicon is a critical element for fabricating most electronic circuits.

<span class="mw-page-title-main">Semiconductor device</span> Electronic component that exploits the electronic properties of semiconductor materials

A semiconductor device is an electronic component that relies on the electronic properties of a semiconductor material for its function. Its conductivity lies between conductors and insulators. Semiconductor devices have replaced vacuum tubes in most applications. They conduct electric current in the solid state, rather than as free electrons across a vacuum or as free electrons and ions through an ionized gas.

<span class="mw-page-title-main">Band gap</span> Energy range in a solid where no electron states exist

In solid-state physics and solid-state chemistry, a band gap, also called a bandgap or energy gap, is an energy range in a solid where no electronic states exist. In graphs of the electronic band structure of solids, the band gap refers to the energy difference between the top of the valence band and the bottom of the conduction band in insulators and semiconductors. It is the energy required to promote an electron from the valence band to the conduction band. The resulting conduction-band electron are free to move within the crystal lattice and serve as charge carriers to conduct electric current. It is closely related to the HOMO/LUMO gap in chemistry. If the valence band is completely full and the conduction band is completely empty, then electrons cannot move within the solid because there are no available states. If the electrons are not free to move within the crystal lattice, then there is no generated current due to no net charge carrier mobility. However, if some electrons transfer from the valence band to the conduction band, then current can flow. Therefore, the band gap is a major factor determining the electrical conductivity of a solid. Substances having large band gaps are generally insulators, those with small band gaps are semiconductor, and conductors either have very small band gaps or none, because the valence and conduction bands overlap to form a continuous band.

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

Gallium arsenide (GaAs) is a III-V direct band gap semiconductor with a zinc blende crystal structure.

<span class="mw-page-title-main">Perovskite (structure)</span> Type of crystal structure

A perovskite is any material with a crystal structure following the formula ABX3, which was first discovered as the mineral called perovskite, which consists of calcium titanium oxide (CaTiO3). The mineral was first discovered in the Ural mountains of Russia by Gustav Rose in 1839 and named after Russian mineralogist L. A. Perovski (1792–1856). 'A' and 'B' are two positively charged ions (i.e. cations), often of very different sizes, and X is a negatively charged ion (an anion, frequently oxide) that bonds to both cations. The 'A' atoms are generally larger than the 'B' atoms. The ideal cubic structure has the B cation in 6-fold coordination, surrounded by an octahedron of anions, and the A cation in 12-fold cuboctahedral coordination. Additional perovskite forms may exist where either/both the A and B sites have a configuration of A1x-1A2x and/or B1y-1B2y and the X may deviate from the ideal coordination configuration as ions within the A and B sites undergo changes in their oxidation states.

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">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">Quantum dot</span> Zero-dimensional, nano-scale semiconductor particles with novel optical and electronic properties

Quantum dots (QDs) or semiconductor nanocrystals are semiconductor particles a few nanometres in size with optical and electronic properties that differ from those of larger particles via quantum mechanical effects. They are a central topic in nanotechnology and materials science. When a quantum dot is illuminated by UV light, an electron in the quantum dot can be excited to a state of higher energy. In the case of a semiconducting quantum dot, this process corresponds to the transition of an electron from the valence band to the conductance band. The excited electron can drop back into the valence band releasing its energy as light. This light emission (photoluminescence) is illustrated in the figure on the right. The color of that light depends on the energy difference between the conductance band and the valence band, or the transition between discrete energy states when the band structure is no longer well-defined in QDs.

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.

<span class="mw-page-title-main">Single crystal</span> Material with a continuous, unbroken crystal lattice

In materials science, a single crystal is a material in which the crystal lattice of the entire sample is continuous and unbroken to the edges of the sample, with no grain boundaries. The absence of the defects associated with grain boundaries can give monocrystals unique properties, particularly mechanical, optical and electrical, which can also be anisotropic, depending on the type of crystallographic structure. These properties, in addition to making some gems precious, are industrially used in technological applications, especially in optics and electronics.

<span class="mw-page-title-main">Pentacene</span> Hydrocarbon compound (C22H14) made of 5 fused benzene rings

Pentacene is a polycyclic aromatic hydrocarbon consisting of five linearly-fused benzene rings. This highly conjugated compound is an organic semiconductor. The compound generates excitons upon absorption of ultra-violet (UV) or visible light; this makes it very sensitive to oxidation. For this reason, this compound, which is a purple powder, slowly degrades upon exposure to air and light.

<span class="mw-page-title-main">Printed electronics</span> Electronic devices created by various printing methods

Printed electronics is a set of printing methods used to create electrical devices on various substrates. Printing typically uses common printing equipment suitable for defining patterns on material, such as screen printing, flexography, gravure, offset lithography, and inkjet. By electronic-industry standards, these are low-cost processes. Electrically functional electronic or optical inks are deposited on the substrate, creating active or passive devices, such as thin film transistors; capacitors; coils; resistors. Some researchers expect printed electronics to facilitate widespread, very low-cost, low-performance electronics for applications such as flexible displays, smart labels, decorative and animated posters, and active clothing that do not require high performance.

Nanoelectronics refers to the use of nanotechnology in electronic components. The term covers a diverse set of devices and materials, with the common characteristic that they are so small that inter-atomic interactions and quantum mechanical properties need to be studied extensively. Some of these candidates include: hybrid molecular/semiconductor electronics, one-dimensional nanotubes/nanowires or advanced molecular electronics.

A definition in semiconductor physics, carrier lifetime is defined as the average time it takes for a minority carrier to recombine. The process through which this is done is typically known as minority carrier recombination.

Black silicon is a semiconductor material, a surface modification of silicon with very low reflectivity and correspondingly high absorption of visible light.

<span class="mw-page-title-main">Crystalline silicon</span> Semiconducting material used in solar cell technology

Crystalline silicon or (c-Si) Is the crystalline forms of silicon, either polycrystalline silicon, or monocrystalline silicon. Crystalline silicon is the dominant semiconducting material used in photovoltaic technology for the production of solar cells. These cells are assembled into solar panels as part of a photovoltaic system to generate solar power from sunlight.

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

Polyfluorene is a polymer with formula (C13H8)n, consisting of fluorene units linked in a linear chain — specifically, at carbon atoms 2 and 7 in the standard fluorene numbering. It can also be described as a chain of benzene rings linked in para positions with an extra methylene bridge connecting every pair of rings.

<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.

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 208. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. Agin, Dan (2007). Junk Science: An Overdue Indictment of Government, Industry, and Faith Groups That Twist Science for Their Own Gain. Macmillan. ISBN   978-0-312-37480-8.
  3. T. Takahashi; T. Takenobu; J. Takeya; Y. Iwasa (2007). "Ambipolar Light-Emitting Transistors of a Tetracene Single Crystal". Advanced Functional Materials. 17 (10): 1623–1628. doi:10.1002/adfm.200700046. S2CID   135786504. Archived from the original on 2012-12-10.
  4. Paderborn University (2024-03-09). "Hawk Supercomputer Improves Solar Cell Efficiency". CleanTechnica. Retrieved 2024-03-10.