Diindenoperylene
Encyclopedia
Diindenoperylene is an organic semiconductor
which receives attention because of its potential application in optoelectronics
(solar cell
s, 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.
The molecular weight is 400.48 g/mol, the dimensions of the molecule in its plane are ~18.4×7 Å. and its sublimation temperature is above 330 °C. It is non-polar and therefore only slightly soluble, for example in acetone
.
DIP is a red dye
and has been used as active material for optical recording
. Because of its ‘perylene-type’ optical emission in the visible spectrum, it has also been used in organic light emitting diodes. Organic field effect transistors of DIP have been studied. The charge carrier mobility achieved was up to 0.1 cm²/(V·s) for thin film transistor
s with silicon dioxide
as gate dielectric
, making DIP a good candidate for further optimisation.
The structure of bulk DIP crystal
s 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. The structure of thin DIP films has been characterized ‘post-growth’, 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.
Organic semiconductor
An organic semiconductor is an organic material with semiconductor properties. Single molecules, short chain and organic polymers can be semiconductive. Semiconducting small molecules include the polycyclic aromatic compounds pentacene, anthracene, and rubrene...
which receives attention because of its potential application in optoelectronics
Optoelectronics
Optoelectronics is the study and application of electronic devices that source, detect and control light, usually considered a sub-field of photonics. In this context, light often includes invisible forms of radiation such as gamma rays, X-rays, ultraviolet and infrared, in addition to visible light...
(solar cell
Solar cell
A solar cell is a solid state electrical device that converts the energy of light directly into electricity by the photovoltaic effect....
s, OLEDs) and electronics
Electronics
Electronics is the branch of science, engineering and technology that deals with electrical circuits involving active electrical components such as vacuum tubes, transistors, diodes and integrated circuits, and associated passive interconnection technologies...
(RFID tags). DIP is a planar perylene
Perylene
Perylene or perilene is a polycyclic aromatic hydrocarbon with the chemical formula C20H12, occurring as a brown solid. It or its derivatives may be carcinogenic, and it is considered to be a hazardous pollutant. In cell membrane cytochemistry, perylene is used as a fluorescent lipid probe...
derivative with two indeno-groups attached to opposite sides of the perylene core. Its chemical formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
is C32H16, the full chemical name is diindeno[1,2,3-cd:1',2',3'-lm]perylene. Its chemical synthesis
Chemical synthesis
In chemistry, chemical synthesis is purposeful execution of chemical reactions to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...
has been described.
The molecular weight is 400.48 g/mol, the dimensions of the molecule in its plane are ~18.4×7 Å. and its sublimation temperature is above 330 °C. It is non-polar and therefore only slightly soluble, for example in acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
.
DIP is a red dye
Dye
A dye is a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and requires a mordant to improve the fastness of the dye on the fiber....
and has been used as active material for optical recording
Optical recording
The history of optical recording can be divided into a few number of distinct major contributions. The pioneers of optical recording worked mostly independently, and their solutions to themany technical challenges have very distinctive features, such as...
. Because of its ‘perylene-type’ optical emission in the visible spectrum, it has also been used in organic light emitting diodes. Organic field effect transistors of DIP have been studied. The charge carrier mobility achieved was up to 0.1 cm²/(V·s) for thin film transistor
Transistor
A transistor is a semiconductor device used to amplify and switch electronic signals and power. It is composed of a semiconductor material with at least three terminals for connection to an external circuit. A voltage or current applied to one pair of the transistor's terminals changes the current...
s with silicon dioxide
Silicon dioxide
The chemical compound silicon dioxide, also known as silica , is an oxide of silicon with the chemical formula '. It has been known for its hardness since antiquity...
as gate dielectric
Gate dielectric
A gate dielectric is a dielectric used between the gate and substrate of a field effect transistor. In state-of-the-art processes, the gate dielectric is subject to many constraints, including:...
, making DIP a good candidate for further optimisation.
The structure of bulk DIP crystal
Crystal
A crystal or crystalline solid is a solid material whose constituent atoms, molecules, or ions are arranged in an orderly repeating pattern extending in all three spatial dimensions. The scientific study of crystals and crystal formation is known as crystallography...
s 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. The structure of thin DIP films has been characterized ‘post-growth’, 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.