128-65-4

Usage

Uses

Used in Organic Field Effect Transistors (OFETs):
PTCDI-Ph is used as a conjugating polymer for the formation of ultrathin films in the fabrication of organic field effect transistors (OFETs). These OFETs are specifically designed for nitrogen dioxide sensor-based applications, where the polymer's high electron affinity and chemical stability play a crucial role in enhancing the device's performance.
Used in Organic Electronic Devices:
As an active layer in the development of organic electronic devices, PTCDI-Ph contributes to the advancement of technology in this field. Its high electron affinity and chemical stability make it an ideal candidate for creating efficient and reliable devices with potential applications in various industries, such as consumer electronics, medical devices, and environmental monitoring systems.

Upstream product

• 128-69-8 perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride 
• 62-53-3 aniline 
• 42944-76-3 1,1'-Binaphthyl-4,4',5,5'-tetracarboxylic acid N,N-diphenyldiimide 
• 56813-69-5 1,3,1',3'-tetraoxo-2,2'-diphenyl-2,3,2',3'-tetrahydro-1H,1'H-[6,6']bi[benzo[de]isoquinolinyl]-7,7'-dicarboxylic acid dimethyl ester 
• 6914-98-3 2-phenylbenzo[de]isoquinoline-1,3-dione 
• 84216-52-4 6-bromo-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 81-32-3 perylene-3,4,9,10-tetracarboxylic acid 

Relevant academic research and scientific papers

Unique aggregate structure of fluoroperylene diimide thin film

A perfluorinated perylene diimide, N,N′-diperfluorophenyl-3,4,9,10- perylenetetracarboxylic diimide (DFPP), and its nonfluorinated analogue, N,N′-diphenyl-3,4,9,10-perylenetetracarboxylic diimide (DPP), showed similar UV-vis absorption and fluorescence spectra when they existed as monomeric dyes in solutions, whereas in solid films they exhibited great differences. Absorption band splitting was observed for DPP film; however, for DFPP film, the fine structure of absorptions similar to that in solution still remained in addition to the absorption peaks becoming broader and shifting to longer wavelength regions. Furthermore, it was found that DFPP molecules aggregated to form a crystalline film when the temperature of the substrate was elevated to 200°C. Through the simulation of the molecular conformation, the theoretical examinations of molecular interactions, the measurement of electron affinity, the observation of the film morphology by AFM and SEM, and the crystalline structure characterization by XRD, the unique aggregate structure of the crystalline DFPP thin film was suggested: DFPP molecules stacked with the perfluorinated phenyl groups straight over or below the perylene cores of the adjacent DFPP molecules.

Green and highly efficient synthesis of perylene and naphthalene bisimides in nothing but water

High-purity, symmetrically substituted perylene and naphthalene bisimides were obtained by hydrothermal condensation of monoamines with the corresponding bisanhydride. The hydrothermal imidization proceeds quantitatively, without the need for organic solvents, catalysts or excess of the amines.

Greener Dye Synthesis: Continuous, Solvent-Free Synthesis of Commodity Perylene Diimides by Twin-Screw Extrusion

A continuous, scalable, and solvent-free method for the synthesis of various naphthalic imides and perylene diimides (PDIs) using twin-screw extrusion (TSE) is reported. Using TSE, naphthalic imides were obtained quantitatively without the need for excess amine reactant or product purification. With good functional-group tolerance, alkyl and benzyl amine derived PDIs (incl. commercial dyes) were obtained in 50–99 % yield. Use of K2CO3, enabled synthesis of more difficult aniline-derived PDIs. Furthermore, an automated continuous TSE process for Pigments Black 31 and 32 is demonstrated, with a throughput rate of about 1500 g day?1, corresponding to a space time yield of about 30×103 kg m?3 day?1, which is 1–2 orders of magnitude greater than for solvent-based batch methods. These methods provide substantial waste reductions and improved efficiency compared to conventional solvent-based methods.

Highly thermal-stable perylene-bisimide small molecules as efficient electron-transport materials for perovskite solar cells

Perylene-bisimide (PDI)-based small molecules (PDI-Ph, PDI-PhCN, PDI-PhCN-2Br and PDI-PhCN-4Br) were synthesized via imidization of perylene bisanhydride and core-bromided perylene bisanhydride. The physical, optical and electronic properties of these molecules were characterized by thermogravimetric analysis (TGA), UV-Vis, X-ray diffraction (XRD), cyclic voltammetry and space charge-limited current (SCLC). PDI-Ph, PDI-PhCN and PDI-PhCN-2Br show excellent thermal stability with decomposition temperatures above 400 °C (610 °C for PDI-PhCN) and high crystallinity with strong π-π stacking. The three molecules also exhibit high electron mobility with average values of 0.169 cm2 V-1 s-1 for PDI-Ph, 0.212 cm2 V-1 s-1 for PDI-PhCN and 0.119 cm2 V-1 s-1 for PDI-PhCN-2Br. Utilizing these molecules as the single electron-transporting layer (ETL), inverted perovskite solar cells with a configuration of ITO/NiOx/MAPbClxI3-x/ETL/Ag were fabricated. A power conversion efficiency of 14.6% was achieved from the device using PDI-PhCN as ETL. Furthermore, when BCP was used as the hole-blocking layer, the identical structured perovskite device achieved a high efficiency of 18.8% for the PDI-PhCN/BCP combination, which was better than the standard cell (17.4%) using C60/BCP as ETL. The superior performance of PDI-PhCN compared to PDI-Ph, PDI-PhCN-2Br and PDI-PhCN-4Br comes from its higher electron mobility and better matched energy levels with that of the absorber MAPbClxI3-x. Our results demonstrate that PDI-based small molecules are very promising electron-transporting materials for highly efficient, low-cost perovskite solar cells. This journal is

A "green" route to perylene dyes: Direct coupling reactions of 1,8-naphthalimide and related compounds under mild conditions using a "new" base complex reagent, t-BuOK/DBN

The direct coupling reactions of 1,8-naphthalimide compounds efficiently occurred at 130 or 170 °C without the intervention of the leuco form dyes in the presence of base complex reagent, t-BuOK/1,5-diazabicyclo[4.3.0]non-5-ene (DBN), to give the corresponding perylene dyes in good yields with >95% purities. A possible mechanistic speculation for these oxidative coupling reactions is briefly discussed.

Perylene derivatives formation in reaction of 3-bromobenzanthrone and 4-bromonaphthalic acid derivatives with a reduction system NiCl2 - 2,2′bipyridyl (or 1,10-phenathroline) - Zn

The reaction of 3-bromobenzanthrone and 4-bromonaphthalic acid derivatives with a reduction system NiCl2-2,2′bipyridyl (or 1,10-phenathroline)-Zn gives rise to compounds containing perylene fragment. Under similar conditions was established a possibility to transform substituted 1,1′-binaphthyls into the corresponding perylene derivatives.

Photoconductivity studies of perylene tetracarbonyl-diimides

Photoconductivity of a series of perylene tetracarboxyl-diimides has been studied by delayed-collection-field and electric field induced fluorescence quenching techniques.It has been shown that these materials exhibit both extrinsic (impurity controlled) and intrinsic carrier generation originating from the first excited singlet state.Perylene tetracarboxyl-diimides are photoactive in the visible spectral range and their carrier generation efficiencies compare well with generation efficiencies in the best known organic photoconductors.This makes them suitable for xerographic application using visible light.

DERIVATIVES OF 1,1'-BINAPHTHYL. IX. FORMATION OF DERIVATIVES OF 3,4,9,10-PERYLENETETRACARBOXYLIC ACID BY ELECTROCHEMICAL REDUCTION OF 8,8'-DISUBSTITUTED DERIVATIVES OF 1,1'-BINAPHTHYL-4,4',5,5'-TETRACARBOXYLIC ACID

The electrochemical reduction of 1,1'-binaphthyl-4,4',5,5'-tetracarboxylic dianhydride, N,N'-diphenyl-1,1'-binaphthyl-4,4',5,5'-tetracarboxydiimide and its 8,8'-dicarboxymethyl derivative, the dianhydride, diimide, and N,N'-diphenyldiimide of 1,1'-binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid, and the N-phenylimide of 1,1'-binaphthyl-4,4',5,5',8,8'-hexacarboxylic monoanhydride in dimethylformamide was studied by polarography, electrosynthesis, and ESR spectroscopy.The corresponding derivatives of 3,4,9,10-perylenetetracarboxylic acid were formed.The radical anion of the carboxylate ion of the initial compound enters into the cyclization of the 1,1'-binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid derivatives.It is suggested, that the cyclization takes place with the initial formation of a bond between the carbon atoms at positin 8 and 8' with subsequent elimination of the substituents.

Soluble Perylene Fluorescent Dyes with High Photostability

The preparation of several 3,4,9,10-perylenebis(dicarboximides) 1 is described and their photostability quantitatively determined and discussed.It is shown, that substitution of the insoluble perylene dye pigments with tert-butyl groups causes solubility in organic solvents leading to high quantum yields of these dyes.