59442-38-5

Basic information

• Product Name: 2,9-Dipropyl-anthra2,1,9-def:6,5,10-d'e'f'diisoquinoline-1,3,8,10-tetrone
• Synonyms: 2,9-Dipropyl-anthra2,1,9-def:6,5,10-d'e'f'diisoquinoline-1,3,8,10-tetrone;2,9-Dipropylanthra[2,1,9-def:6,5,10-d′e′f′]diisoquinoline-1,3,8,10(2H,9H)tetrone;Bis(n-propylimido)perylene;PDI-C3;Perylene-3,4,9,10-tetracarboxylic acid bis(propylimide);2,9-Dipropylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)tetrone 97%
• CAS NO: 59442-38-5
• Molecular Formula: C₃₀H₂₂N₂O₄
• Molecular Weight: 474.514
• Product Categories: electronic
• Mol File: 59442-38-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: >300°C
• Appearance: /
• CAS DataBase Reference: 2,9-Dipropyl-anthra2,1,9-def:6,5,10-d'e'f'diisoquinoline-1,3,8,10-tetrone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,9-Dipropyl-anthra2,1,9-def:6,5,10-d'e'f'diisoquinoline-1,3,8,10-tetrone(59442-38-5)
• EPA Substance Registry System: 2,9-Dipropyl-anthra2,1,9-def:6,5,10-d'e'f'diisoquinoline-1,3,8,10-tetrone(59442-38-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 59442-38-5(Hazardous Substances Data)

Usage

Uses

High electron transporting character; Perylenebis(dicarboximide)s (PDIs) can be used as air-stable n-type semiconductor materials for organic fieldeffect transistors (OFETs);Excellent candidates as electron accepting building blocks for organic photovoltaics (OPVs).

General Description

2,9-Dipropylanthra[2,1,9-def:6,5,10-d′e′f′]diisoquinoline-1,3,8,10(2H,9H)tetrone belongs to the class of perylenebis(dicarboximide) (PDI) that has an electron transporting character. It can be used as an air-stable n-type semiconductor material in organic field effect transistors. It can also be used as an acceptor molecule in organic photovoltaics.

Upstream product

• 128-69-8 perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride 
• 109-73-9 N-butylamine 
• 107-10-8 propylamine 

Downstream Products

• 70654-98-7 perylene-3,4,9,10-tetracarboxylic acid monoanhydride mono(n-propyl)imide 
• 128-69-8 perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride 
• 530086-49-8 1,6,7,12-tetrakis(4-n-butyloxyphenoxy)perylene-3,4,9,10-tetracarboxylic acid dianhydride 
• 156028-30-7 1,6,7,12-tetrakis(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid dianhydride 
• 1234347-63-7 N,N'-bis-n-propyl-1,6,7,12-tetrakis(4-n-butyloxyphenoxy)perylene-3,4,9,10-tetracarboxdiimide 
• 185552-14-1 N,N'-bis-n-propyl-1,6,7,12-tetrakis(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxdiimide 

Relevant articles and documents

Design and synthesis of novel fluorescence sensing perylene diimides based on photoinduced electron transfer

Two novel tetraester- and PAMAM-branched perylene diimides were synthesized and configured as "fluorophore-spacer-receptor" systems based on photoinduced electron transfer. Due to their long alkylester and alkylamine terminal groups the examined compounds were well soluble in organic solvents. Photophysical characteristics of the dyes were investigated in DMF and water/DMF (1:1, v/v) solution. The ability of the synthesized perylene diimides to detect cations was evaluated by the changes in their fluorescence intensity in the presence of metal ions (Zn2+, Co2+, Cu2+, Fe3+, Pb2+, Hg2+, Ag+ and Ni 2+) and protons. The dyes under study displayed "off-on" switching in its fluorescence as a function of pH, which is attributed to disallowing photoinduced electron transfer from the receptor moiety to the fluorophore. PAMAM-branched dye displayed a good pH sensor activity (FE = 6.4), however the pH sensing ability of tetraester was substantially higher (FE = 184). In the presence of Cu2+ and Pb2+ ions tetraester quenched its fluorescence intensity (FQ = 22 and 12 respectively), while PAMAM-branched dye enhanced its fluorescence intensity with pronounced selectivity to Cu2+ and Fe3+ (FE = 3.2 and 4.9, respectively). The results obtained indicate the potential of the novel compounds as fluorescent detectors for metal ions with pronounced selectivity towards Cu2+, Pb2+ and Fe3+ ions and highly efficient "off-on" pH switches, especially a tetraester-branched perylene diimide.

Synthesis and optical properties of n-type polymers containing perylene moieties

Three n-type polymers, Ppe01, Ppe02, and Ppe03, containing both perylene moieties and fluorine atoms were synthesized. The synthesiszed polymeric perylene derivatives with good compatibility for solution processes were chosen as new acceptor candidates fo

The Relation between Packing Effects and Solid State Fluorescence of Dyes

The solid state fluorescence of diketopyrrolopyrrole dyes and perylene-3,4:9,10-tetracarboxylic bisimides with alkyl substituents are investigated and compared with noncovalent interactions.The latter are estimated by crystal structure analysis, heats and entropies of fusion and solubilities in organic solvents.Applications of the dyes are discussed.