188-94-3

Basic information

• Product Name: DIINDENO[1,2,3-C,D-1',2',3'-I,M]PERYLENE
• Synonyms: DIINDENO[1,2,3-C,D-1',2',3'-I,M]PERYLENE;PERIFLANTHENE;diindeno[1,2,3-cd:1',2',3'-lm]perylene;Diindeno[1,2,3-c,d-1μ,2μ,3μ-l,m]perylene solution;Einecs 205-875-4;1',2',3'-lm]perylene;Diindeno[1,2,3-cd;DIP
• CAS NO: 188-94-3
• Molecular Formula: C₃₂H₁₆
• Molecular Weight: 400.47
• EINECS: 205-875-4
• Mol File: 188-94-3.mol

Chemical Properties

• Melting Point: >400 °C
• Flash Point: 6 °C
• Appearance: orange solid
• Density: 1.467
• Storage Temp.: -20°C
• CAS DataBase Reference: DIINDENO[1,2,3-C,D-1',2',3'-I,M]PERYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: DIINDENO[1,2,3-C,D-1',2',3'-I,M]PERYLENE(188-94-3)
• EPA Substance Registry System: DIINDENO[1,2,3-C,D-1',2',3'-I,M]PERYLENE(188-94-3)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-38-48/20-63-65-67
• Safety Statements: 36/37-62
• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 188-94-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics Industry:
Diindeno[1,2,3-c,d-1',2',3'-i,m]perylene is used as a key component in organic light-emitting diodes (OLEDs) for its high thermal and chemical stability, which contributes to the device's performance and longevity. Its strong fluorescent characteristics enhance the light emission properties of OLEDs.
Also in Organic Electronics Industry:
In organic photovoltaic (OPV) devices, Diindeno[1,2,3-c,d-1',2',3'-i,m]perylene serves as a semiconductor material, leveraging its excellent semiconducting properties to improve the efficiency and stability of solar cells.
Environmental Considerations:
Diindeno[1,2,3-c,d-1',2',3'-i,m]perylene is found in environmental samples such as soil, sediment, and air, originating from the incomplete combustion of organic matter. Recognized as a priority pollutant, it possesses potential carcinogenic and mutagenic properties. Therefore, it is crucial to handle and dispose of this compound with care to mitigate exposure risks and reduce its environmental impact.

Synthetic route

fluoranthene (206-44-0) → Diindeno<1,2,3-c,d:1',2',3'-lm>perylene (188-94-3)

Conditions	Yield
With sodium amide In N,N-dimethyl acetamide at 162.5 - 165.5℃; for 10h; Temperature; Solvent; Inert atmosphere;	46.7%
With sodium amide; decalin at 200℃;
With sodium amide; decalin at 200℃;

PERYLENE (198-55-0) + benzene (71-43-2) → Diindeno<1,2,3-c,d:1',2',3'-lm>perylene (188-94-3)

Conditions	Yield
With aluminium trichloride zuletzt bei Siedetemperatur;

fluoranthene (206-44-0) + sodium amide + decalin (91-17-8) → Diindeno<1,2,3-c,d:1',2',3'-lm>perylene (188-94-3)

Conditions	Yield
at 200℃;
at 200℃;

bifluoranthenyl-(3.3') → Diindeno<1,2,3-c,d:1',2',3'-lm>perylene (188-94-3)

Conditions	Yield
With sodium amide; decalin at 200℃;
With sodium amide; decalin at 200℃;

Diindeno<1,2,3-c,d:1',2',3'-lm>perylene (188-94-3) → 1,2,3,4,4a,8b,9,10,11,12,12a,16b-dodecahydro-diindeno[1,2,3-cd;1',2',3'-lm]perylene

Conditions	Yield
With nickel at 270℃; under 183877 Torr; Hydrogenation;
Multi-step reaction with 2 steps 1: nickel; decalin / 270 °C / Hydrogenation 2: selenium / 300 °C View Scheme

Diindeno<1,2,3-c,d:1',2',3'-lm>perylene (188-94-3) → 1,2,3,4,4a,4b,5,6,6a,8b,9,10,11,12,12a,16b-hexadecahydro-diindeno[1,2,3-cd;1',2',3'-lm]perylene (860549-06-0)

Conditions	Yield
With nickel; decalin at 270℃; Hydrogenation;

Diindeno<1,2,3-c,d:1',2',3'-lm>perylene (188-94-3) → diindeno[1,2,3-cd;1',2',3'-lm]perylene-6,7-dione (103283-39-2)

Conditions	Yield
With sodium dichromate; acetic acid; nitrobenzene

Diindeno<1,2,3-c,d:1',2',3'-lm>perylene (188-94-3) + decalin (91-17-8) + nickel → 1,2,3,4,4a,4b,5,6,6a,8b,9,10,11,12,12a,16b-hexadecahydro-diindeno[1,2,3-cd;1',2',3'-lm]perylene (860549-06-0) + 1.2.3.4.4a.8b.9.10.11.12.12a.16b-dodecahydro-diindeno<1.2.3-cd:1'.2'.3'-lm>perylene (?)

Conditions	Yield
at 270℃; under 183877 Torr; Hydrogenation;

Upstream product

• 206-44-0 fluoranthene 
• 91-17-8 decalin 
• 198-55-0 PERYLENE 
• 71-43-2 benzene 

Relevant articles and documents

DIINDENOPERYLENE DIANION. LOCAL vs. PERIPHERAL CONTRIBUTIONS TO THE AROMATIC CHARACTER

Diindenoperylene (1) is shown to undergo a two electron reduction process to its dianion 2.Both neutral and doubly charged systems exhibit an enhanced diamagnetic character which is belived to be acquired via two different mechanisms.

Electronic structure of diindenoperylene radical anion

The electronic structure of diindenoperylene (periflanthene) radical anion has been studied on the basis of the ESR, electronic absorption, and linear dichroism spectra.The observed results are interpreted in terms of the SCF MO calculations within the framework of the ?-electron approximation.

A two-[...] synthetic method

The invention discloses a method for synthesizing periflanthene. The method comprises the following steps that fluoranthene, sodamide and organic solvent are added to a reaction container, inert gas is charged into the reaction container, then heating is carried out to carry out a synthetic reaction, and a mixed solution of the periflanthene is obtained; after the mixed solution with the periflanthene is cooled, absolute ethyl alcohol is dropwise added, then water is dropwise added, and periflanthene crude products are obtained through filtering. Compared with the prior art, the method has the advantages that reaction path raw materials can be obtained easily, cost is low, the yield is high, the technological requirement is low, operation is easy, the reaction process and aftertreatment are safe, purification is easy, and industrial production is facilitated.