Diindenoperylene Chemical Properties

Melting point:

>400 °C

Density 

1.467

Flash point:

6 °C

storage temp. 

Sealed in dry,Room Temperature

InChI

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

InChIKey

BKMIWBZIQAAZBD-UHFFFAOYSA-N

SMILES

C1C2C3C(=C4C5=C6C(=C7C(=C6C=C4)C=CC=C7)C=CC5=2)C=CC2=C4C(=C(C2=3)C=1)C=CC=C4

Safety Information

Hazard Codes 

F,Xn

Risk Statements 

11-38-48/20-63-65-67

Safety Statements 

36/37-62

RIDADR 

2811

HazardClass 

6.1(b)

PackingGroup 

III

Diindenoperylene Usage And Synthesis

Description

Diindenoperylene (DIP), also known as diindeno[1,2,3-cd:1',2',3'-lm]perylene, 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.

Uses

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.

Synthesis

1. Pre-grind the sodium amide flakes into powder, preventing moisture absorption during handling. 2. Under the protection of nitrogen, 20 g of fluoranthene, 10 g of powdered sodium amide and 60 g of N,N-dimethylacetamide were added to the first reaction vessel. The temperature was slowly raised to 164±1.5°C and the reaction was continuously stirred for 10 hours to obtain a dark blue to black mixed solution containing indeno[1,2,3-cd:1',2',3'-lm]hydrazone. 3. The reaction mixture was cooled to 10 °C, 60 g of anhydrous ethanol was added slowly dropwise, and the temperature of the solution was controlled not to exceed 20 °C. The reaction mixture was cooled to 10 °C, and 60 g of anhydrous ethanol was added slowly. After the temperature was stabilized, 80 g of water was added slowly to produce a deep red solid precipitate. Keep the temperature ≤ 20 ℃ during dropwise addition and stir at room temperature for 6 hours. 4. The precipitate was collected by filtration, washed to neutral, and dried at 80 °C for 6 h. 15 g of crude indeno[1,2,3-cd:1',2',3'-lm]perylene was obtained in 75.7% yield. 5. The crude product was crushed and added to the second reactor, 1 g of toluene was added, heated to reflux and kept for 3 hours. After filtration, the filter cake was dried at 80°C for 4 hours to give 6 g of magenta colored solid powder (first material) in 40% yield. After liquid chromatography analysis, the content of indeno[1,2,3-cd:1',2',3'-lm]hydrazone was 96.2%. 6. The first material was added to the third reaction vessel with 90 g of toluene and heated to reflux for 3 hours. After filtration, the filter cake was dried at 80 °C for 4 h. 2.8 g of magenta solid powder (second material) was obtained in 46.7% yield. The content of indeno[1,2,3-cd:1',2',3'-lm]hydrazone was analyzed by liquid chromatography as 98.4%.

References

1. High structural order in thin films of the organic semiconductor diindenoperylene DOI:10.1063/1.1508436
2. Optical properties and morphology of thin diindenoperylene films DOI:10.1016/J.JLUMIN.2004.08.023
3. High Fill Factor and Open Circuit Voltage in Organic Photovoltaic Cells with Diindenoperylene as Donor Material, Adv. Funct. Mater. 2010, 20, 4295–4303；DOI:10.1002/adfm.201001028
4. Rapid roughening in thin film growth of an organic semiconductor (diindenoperylene). DOI:10.1103/PHYSREVLETT.90.016104

Diindenoperylene(188-94-3)Related Product Information

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