Diindenoperylene

Last updated
Diindenoperylene
Periflanthene.png
Diindenoperylene-3D-balls.png
Names
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
PubChem CID
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).
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Infobox references

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]

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

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References

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