Perylene CAS 198-55-0

Perylene, CAS 198-55-0, molecular formula C20H12, is a polycyclic aromatic hydrocarbon that appears as a brown solid at room temperature and pressure. Its highly conjugated electronic structure gives it significant spectral properties. It has a strong absorption peak in the ultraviolet visible region, which is related to its large-scale π - π * transitions.

This spectral characteristic makes perylne an excellent fluorescent material, capable of emitting strong fluorescence under specific wavelength light excitation. It is a parent compound of Rylene dye, which has extremely strong fluorescence properties. Its luminescence efficiency and stability make it excellent in various applications. Its fluorescence characteristics are commonly used in probe design, labeling, sensor and dye development. It is worth noting that derivatives of this substance may cause cancer and are considered harmful pollutants. They are toxic when inhaled or in contact with the skin and can cause irreversible damage to the body.

Perylene, with the chemical formula C20H12, is an organic compound with unique properties. Its unique molecular structure and chemical properties make perylne have broad application prospects in multiple fields.

 

The Important Role Of Organic Synthesis

As an organic synthesis intermediate, its importance is self-evident. In organic chemical reactions, it can act as a reactant, catalyst, or ligand, participate in various chemical reactions, and thus prepare other organic compounds with specific functions. These compounds have a wide range of applications in industries such as pharmaceuticals, pesticides, dyes, coatings, etc.

(1) In The Field Of Medicine:

Derivatives of perylne can be used as part of drug molecules with specific biological activities, such as antibacterial, anti-inflammatory, anti-tumor, etc. Through rational drug design, perylne can be introduced into drug molecules, thereby improving drug efficacy and reducing side effects.

(2) Pesticide Field:

Some derivatives of perylne have insecticidal, bactericidal, or herbicidal activities and can be used to prepare highly efficient and low toxicity pesticide products. These pesticide products are of great significance in protecting crops from the invasion of pests and diseases.

(3) In The Field Of Dyes And Coatings:

Derivatives of perylne have excellent color properties and stability, and can be used as raw materials for dyes or pigments. They can be used in industries such as textiles, plastics, rubber, coatings, etc. to provide products with bright and long-lasting colors.

Star Molecules Of Optoelectronic Materials

 

The application of perylne in the field of optoelectronic materials has also attracted much attention. Its unique molecular structure and optical properties make perylne an ideal choice for preparing high-performance optoelectronic materials.

(1) Organic Solar Cells:

Derivatives of perylne can serve as acceptor materials in organic solar cells, forming heterojunction structures with donor materials to improve the photoelectric conversion efficiency of solar cells.

 

(2) Organic Light Emitting Diodes (OLEDs):

Derivatives of perylne can also be used as luminescent materials in OLEDs, and by adjusting their molecular structure and luminescent properties, different colored luminescent effects can be achieved. This is of great significance for the preparation of high-performance and low-power OLED displays.

(3) Organic Field Effect Transistor (OFET):

Derivatives of perylne can also be used as semiconductor materials in OFETs, with excellent carrier mobility and stability. This is of great significance for the preparation of high-performance and low-cost electronic devices.

Fluorescent Probes For Cell Chemistry

 

In the field of cell chemistry, perylne is also used as a fluorescent probe for labeling and detecting lipid components on cell membranes. This application is mainly due to the hydrophobicity and strong fluorescence properties of perylne.

(1) Cell membrane markers:

Derivatives of perylne can bind with lipid components on the cell membrane to form stable fluorescent complexes. By observing under a fluorescence microscope, the structure and distribution of the cell membrane can be clearly seen.

(2) Cell imaging:

By utilizing the fluorescence properties of perylne, imaging studies of cells can also be conducted. By adjusting the molecular structure and excitation wavelength of perylne, fluorescence imaging effects of different colors can be achieved. This is of great significance for studying the morphology, structure, and function of cells.

The Diverse Applications Of Biochemical Reagents

 

Perylene can also be used as a biochemical reagent for life science related research. Its unique chemical and fluorescent properties make perylne have broad application prospects in the field of biochemistry.

(1) Probe Design:

Derivatives of perylne can serve as probe molecules for detecting specific molecules or ions in living organisms. By designing a reasonable probe structure, high sensitivity and selectivity detection can be achieved.

(2) Marking Technology:

The fluorescence properties of perylne can also be used to label biomolecules such as proteins, nucleic acids, etc. Through labeling technology, the localization, tracking, and quantitative analysis of biomolecules can be achieved.

(3) Sensor Development:

Derivatives of perylne can also serve as sensitive components for sensors, used to detect environmental changes or physiological processes within living organisms. These sensors have broad application prospects in fields such as biomedical and environmental monitoring.

The Innovation Source Of Luminescent New Materials

 

Perylne, as a raw material for the preparation of luminescent new materials, has also shown great potential for application. Its unique luminescent properties and stability make perylne an ideal choice for preparing high-performance luminescent new materials.

(1) Light Emitting Diodes (LEDs):

Derivatives of perylne can be used as luminescent materials for LEDs, and by adjusting their molecular structure and luminescent properties, different colors of LED light sources can be achieved. This is of great significance for the preparation of high-performance and low-power LED light sources.

 

(2) Laser Material:

Derivatives of perylne can also be used as raw materials for laser materials to prepare high-performance lasers. These lasers have broad application prospects in fields such as communication, healthcare, and scientific research.

(3) Other Luminescent Materials:

In addition to LED and laser materials, derivatives of perylne can also be used to prepare other types of luminescent materials, such as phosphors, quantum dots, etc. These materials also have broad application prospects in fields such as lighting, display, and sensing.

 

Blue Light Hole Transport Materials for QLED Quantum Dot Display

In the new generation of quantum dot light-emitting diode (QLED) display technology, polyimide derivatives of perylene have been developed as high-performance blue light hole transport materials. Traditional QLED hole transport materials generally suffer from low hole mobility and mismatch with the energy levels of quantum dot luminescent layers. However, the hole mobility of perylene imide derivatives reaches 0.8 cm ²/(V · s), and their HOMO energy level perfectly matches the energy level of blue light quantum dots,

 

which can greatly improve the injection efficiency of holes into the luminescent layer. The QLED blue light device prepared using this perylene based hole transport material has improved current efficiency by 120% and extended the device's working life by 2.5 times, completely solving the long-standing bottleneck of blue light device life that has hindered the development of the QLED industry. At present, this technology has entered the pilot production stage and will be widely applied in the next generation of printed display panels in the future.

The steps of one synthesis method are: synthesis at 80 ° C, introducing 200 g of phenol. Add 0.1 mole of perylene tetracarboxylic acid dianhydride (per acid) and 0.3 mole of diethanolamine, and heat the batch to 120 ° C within 30 minutes. Mix it with 0.225 mol of p-trifluoromethoxyaniline, then heat at 150 ℃ for 5 hours and distill to remove phenol/water. Subsequently, the batch of material was indirectly cooled to 90 ℃ and 280g of methanol was added dropwise. Then cool to 40 ° C and isolate. Wash the product with 500g of methanol and then with 500g of water. Introduce the wet filter cake into 800 ml of 5% concentration KOH solution, heat the system to 80 ℃ and stir for 1 hour, separate the product, wash with water until neutral, and dry. Dissolve the product in 1500 g of sulfuric acid at 20 ° C and slowly discharge into 2000 ml of methanol at approximately 60 ° C. Dilute the mixture with water, filter and separate the product, wash and dry. Yield: 95% perylene of formula (II).

The specific synthesis steps involve reacting naphthalene (Sigma Aldrich Corporation) in a NaNO2 TfOH (Tf=CF3SO2) solution to obtain binaphthalene from naphthalene. Reacting naphthalene methyl in the presence of LiTHF under oxygen bubbling to obtain perylne. SbF5 purchased from Sigma Aldrich Corporation was diluted twice in a dry argon atmosphere. SO2ClF was prepared from SO2Cl2 previously prepared in the halogen exchange reaction between NH4F and TFA. Reacting perylne with SbF5-SO2ClF and purifying the product by HPLC to obtain dibenzo perylne. Allow NCS to react with one equivalent of dibenzo perylne in AcOH in the presence of CHCl3 for chlorination. Then react the product with n-BuLi and Si (OC2H5) 4 in THF solution to obtain perylne.

Main categories:
Perylne based pigments with perylnetetracarbodiimide as the parent structure are an important variety, which have excellent sun resistance, heat resistance, and solvent resistance, and are widely used for coloring plastics and synthetic fiber raw materials.

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