Perylenebisimide with extended PI system

Base Information

• Chemical Name: Perylenebisimide with extended PI system
• CAS No.: 55034-79-2
• Molecular Formula: C36H16N4O2
• Molecular Weight: 536.549
• DSSTox Substance ID: DTXSID801146683
• Nikkaji Number: J1.314.396J
• Mol file: 55034-79-2.mol

Synonyms:PTCBI;PTCBI,trans;55034-79-2;PERYLENEBISIMIDE WITH EXTENDED PI SYSTEM;SCHEMBL269002;DTXSID801146683;D92189;N,N'-Diphenylglyoxaline-3,4,9,10-perylenetetracarboxylic acid diacidamide;Bisbenzimidazo[2,1-a:2',1'-a']anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-10,21-dione, 97%;Dibenzimidazo[2,1-a:2',1'-a']anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline- 10,21-dione

Chemical Property of Perylenebisimide with extended PI system

Chemical Property:

• Melting Point: >300°C
• PSA: 68.72000
• LogP: 1.94240
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 536.12732577
• Heavy Atom Count: 42
• Complexity: 1100

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bisbenzimidazo[2,1-a:2′,1′-a′]anthra[2,1,9-def:6,5,10-d′e′f′]diisoquinoline-10,21-dione 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N=C3N2C(=O)C4=CC=C5C6=C7C(=CC=C8C7=C(C=C6)C9=NC1=CC=CC=C1N9C8=O)C1=C5C4=C3C=C1
• Uses: Excellent materials as electron accepting building blocks for organic photovoltaics (OPVs); organic field effect transistors (OFETs); organic photoconductive sensors and organic electroluminescent cells.

Technology Process of Perylenebisimide with extended PI system

There total 2 articles about Perylenebisimide with extended PI system which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one (23749-58-8) → bisbenzimidazo[2,1-a:2',1'-a']anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-10,21-dione (55034-79-2)

Guidance literature:

With 2,6-dichloro-benzonitrile; potassium tert-butylate; In quinoline; at 170 ℃;

DOI:10.1021/jo0010835

Reference yield:

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) + 1,2-diamino-benzene (95-54-5) → bisbenzimidazo[2,1-a:2',1'-a']anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-10,21-dione (55034-79-2) + bisbenzimidazo[2,1-a:1',2'-b']anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-6,11-dione (55034-81-6)

Guidance literature:

With piperazine; phenol; at 70 - 180 ℃; for 8h; Melt;

upstream raw materials:

benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

1,2-diamino-benzene

Refernces

• 1、 Perrin, Lara,Hudhomme, Pietrick. "Synthesis, electrochemical and optical absorption properties of new perylene-3,4:9,10-bis(dicarboximide) and perylene-3,4:9,10-bis(benzimidazole) derivatives". experimental part. p. 5427 - 5440. Retrieved 2011/11/29.
• 2、 -. "METHODS FOR PREPARING PERYLENE/PERINONE PIGMENTS". Page/Page column 3. . Retrieved 2008/12/06.