2,9-Diphenylanthra(2,1,9-def:6,5,10-d'e'f')diisoquinoline-1,3,8,10(2H,9H)-tetrone

Base Information

• Chemical Name: 2,9-Diphenylanthra(2,1,9-def:6,5,10-d'e'f')diisoquinoline-1,3,8,10(2H,9H)-tetrone
• CAS No.: 128-65-4
• Molecular Formula: C36H18 N2 O4
• Molecular Weight: 542.55
• European Community (EC) Number: 204-902-7
• DSSTox Substance ID: DTXSID60155767
• Nikkaji Number: J184.365F
• Wikidata: Q72473428
• Mol file: 128-65-4.mol

Synonyms:128-65-4;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;DP-PTCDI;EINECS 204-902-7;Anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone, 2,9-diphenyl-;n,n'-diphenyl-3,4,9,10-perylene dicarboximide;2,9-Diphenylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone;7,18-diphenyl-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone;2,9-diphenylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2h,9h)-tetrone;Anthra(2,1,9-def:6,5,10-d'e'f')diisoquinoline-1,3,8,10(2H,9H)-tetrone, 2,9-diphenyl-;N,N'-Diphenyl-3,4:9,10-perylenebisdicarbimide;SCHEMBL1127945;DTXSID60155767;C36H18N2O4;AKOS000506018;C36-H18-N2-O4;AS-39339;Perylenetetracarboxylic N,N'-bis(phenylimide);N,N?-Diphenyl-3,4,9,10-perylenedicarboximide;Perylenetetracarboxylic N,N/'-bis(phenylimide);N,N'-Diphenyl-3,4,9,10-perylenedicarboximide, 98%;N,N'-Diphenylperylene-3,4:9,10-bis(dicarboximide);3,4,9,10-Perylenetetracarboxylic 3,4:9,10-diimide, N,N'-diphenyl-;N,N inverted exclamation mark -Diphenyl-3,4,9,10-perylene dicarboximide;2,9-Diphenylanthra[2,1,9-def:6,5,10-d'e'f]diisoquinoline-1,3,8,10(2H,9H)-tetrone

Chemical Property of 2,9-Diphenylanthra(2,1,9-def:6,5,10-d'e'f')diisoquinoline-1,3,8,10(2H,9H)-tetrone

Chemical Property:

• Melting Point: >300 °C
• PSA: 78.14000
• Density: 1.546g/cm3
• LogP: 5.94140
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 542.12665706
• Heavy Atom Count: 42
• Complexity: 1010

Purity/Quality:

98%min ^*data from raw suppliers

N,N′-Diphenyl-3,4,9,10-perylenedicarboximide 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C(=O)C3=C4C(=CC=C5C4=C(C=C3)C6=C7C5=CC=C8C7=C(C=C6)C(=O)N(C8=O)C9=CC=CC=C9)C2=O
• 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.

Technology Process of 2,9-Diphenylanthra(2,1,9-def:6,5,10-d'e'f')diisoquinoline-1,3,8,10(2H,9H)-tetrone

There total 9 articles about 2,9-Diphenylanthra(2,1,9-def:6,5,10-d'e'f')diisoquinoline-1,3,8,10(2H,9H)-tetrone 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: 47.0%

2-phenylbenzo[de]isoquinoline-1,3-dione (6914-98-3) → 2,9-diphenylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone (128-65-4)

Guidance literature:

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

DOI:10.1021/jo0010835

Reference yield: 23.0%

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) + aniline (62-53-3) → 2,9-diphenylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone (128-65-4)

Guidance literature:

With potassium carbonate; In neat (no solvent); at 150 ℃; for 1h; Green chemistry;

DOI:10.1002/anie.201913625

Reference yield:

6-bromo-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (84216-52-4) → 2-phenylbenzo[de]isoquinoline-1,3-dione (6914-98-3) + 2,9-diphenylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone (128-65-4)

Guidance literature:

6-bromo-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione; With [2,2]bipyridinyl; nickel dichloride; zinc; In N,N-dimethyl-formamide; at 70 ℃; for 6h;

With dihydrogen peroxide; In N,N-dimethyl-formamide; at 30 - 40 ℃; for 0.5h;

DOI:10.1007/bf02757446

upstream raw materials:

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

aniline

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

1,1'-Binaphthyl-4,4',5,5'-tetracarboxylic acid N,N-diphenyldiimide

Refernces

• 1、 Baumgartner, Bettina,Svirkova, Anastasiya,Bintinger, Johannes,Hametner, Christian,Marchetti-Deschmann, Martina,Unterlass, Miriam M.. "Green and highly efficient synthesis of perylene and naphthalene bisimides in nothing but water". . p. 1229 - 1232. Retrieved 2017.
• 2、 Gong, Yuancai,He, Zhaoxia,Huang, Wei,Jiang, Jingjing,Lu, Di,Xia, Ruidong,Xin, Hao,Yan, Weibo,Yang, Wensheng. "Highly thermal-stable perylene-bisimide small molecules as efficient electron-transport materials for perovskite solar cells". supporting information. p. 14773 - 14781. Retrieved 2020/11/17.