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]
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Preferred IUPAC name
Diindeno[1,2,3-cd:1′,2′,3′-lm]perylene | |
Other names
Periflanthen; Periflanthene
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Identifiers | |
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3D model (JSmol)
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Abbreviations | DIP |
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ECHA InfoCard | 100.005.343 |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C32H16 | |
Molar mass | 400.480 g·mol−1 |
Appearance | Orange 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
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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]