128-65-4

Basic information

• Product Name: N,N'-DI-PHENYL-PERYLENE-TETRACARBONIC ACID, DIAMIDE
• Synonyms: PTCDI-PH;N,N'-DI-PHENYL-PERYLENE-TETRACARBONIC ACID, DIAMIDE;N,N'-DIPHENYL-3,4,9,10-PERYLENEDICARBOXIMIDE;2,9-diphenylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone;2,9-Diphenyl-anthra2,1,9-def:6,5,10-d'e'f'diisoquinoline-1,3,8,10-tetrone;N,N-Diphenyl-3,4:9,10-perylenetetracarboxylic acid diimide;2,9-Diphenyl-2,9-diazadibenzo[cd,lm]perylene-1,3,8,10-tetrone;N,N'-Diphenyl-3,4:9,10-perylenebisdicarbimide
• CAS NO: 128-65-4
• Molecular Formula: C₃₆H₁₈N₂O₄
• Molecular Weight: 542.54
• EINECS: 204-902-7
• Product Categories: electronic;OTFT/OFET/OPV Materials
• Mol File: 128-65-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: >300 °C
• Appearance: /
• CAS DataBase Reference: N,N'-DI-PHENYL-PERYLENE-TETRACARBONIC ACID, DIAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-DI-PHENYL-PERYLENE-TETRACARBONIC ACID, DIAMIDE(128-65-4)
• EPA Substance Registry System: N,N'-DI-PHENYL-PERYLENE-TETRACARBONIC ACID, DIAMIDE(128-65-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 128-65-4(Hazardous Substances Data)

Usage

Uses

PTCDI-Ph is a conjugating polymer that forms an ultrathin film that can be used in the fabrication of organic field effect transistors (OFETs) for nitrogen dioxide sensor based applications.

General Description

N,N′-Diphenyl-3,4,9,10-perylenedicarboximide (PTCDI-Ph) is an asphaltene based conducting polymer that has an archipelago model. It is a perylene diimide derivative that has a high electron affinity and shows good chemical stability. It can be used as an active layer in the development of organic electronic devices.

Upstream product

• 81-32-3 perylene-3,4,9,10-tetracarboxylic acid 
• 62-53-3 aniline 
• 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 
• 42944-76-3 1,1'-Binaphthyl-4,4',5,5'-tetracarboxylic acid N,N-diphenyldiimide 
• 128-69-8 perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride 

Relevant articles and documents

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.

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.

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.