Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile

Base Information

• Chemical Name: Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile
• CAS No.: 215611-93-1
• Molecular Formula: C16H6N6
• Molecular Weight: 282.264
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20474668
• Nikkaji Number: J1.027.283A
• Wikidata: Q72503361
• Mol file: 215611-93-1.mol

Synonyms:Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile;215611-93-1;PPDN;SCHEMBL185217;DTXSID20474668;MFCD12022437;SB66769;CS-0378826;FT-0746222;1,4,8,9-TETRAAZATRIPHENYLENE-2,3-DICARBONITRILE;2,2-(VINYLENEDI-P-PHENYLENE)BIS[5-TERT-OCTYLBENZOXAZOLE]

Chemical Property of Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile

Chemical Property:

• Melting Point: >250 °C(Solv: ethanol (64-17-5))
• Boiling Point: 654.1±55.0 °C(Predicted)
• PKA: -5.11±0.50(Predicted)
• PSA: 99.14000
• Density: 1.54
• LogP: 2.46956
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 282.06539422
• Heavy Atom Count: 22
• Complexity: 481

Purity/Quality:

98% ^*data from raw suppliers

Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C3=C(C=CC=N3)C4=NC(=C(N=C24)C#N)C#N)N=C1
• Description: PPDN has a chemical structure of phenanthroline in conjugation with dicarbonitrile-substituted pyrazine. As PPDN is electron-deficient, it can be used as an electron-transport layer (ETL) or hole-injection layer (HIL) material in organic electronic devices.

Technology Process of Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile

There total 6 articles about Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile 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: 91.0%

1,10-phenanthroline-5,6-dione (27318-90-7) + diaminomaleonitrile (1187-42-4) → 2,3-dicyanodipyrido<3,2-f:2',3'-h>quinoxaline (215611-93-1)

Guidance literature:

In ethanol; water; at 180 ℃; for 24h;

DOI:10.1080/00397910600781323

Reference yield: 87.0%

1,10-phenanthroline-5,6-dione (27318-90-7) + 1,2-diamino-1,2-dicyanoethylene (54848-44-1) → 2,3-dicyanodipyrido<3,2-f:2',3'-h>quinoxaline (215611-93-1)

Guidance literature:

In ethanol; for 5h; Inert atmosphere; Reflux;

DOI:10.1016/j.poly.2012.12.003

Reference yield: 80.0%

1,10-Phenanthroline (66-71-7) + diaminomaleonitrile (1187-42-4) → 2,3-dicyanodipyrido<3,2-f:2',3'-h>quinoxaline (215611-93-1)

Guidance literature:

In ethanol; for 1h; Reflux; Inert atmosphere;

DOI:10.1039/c4nj01938e

upstream raw materials:

1,10-phenanthroline-5,6-dione

diaminomaleonitrile

1,2-diamino-1,2-dicyanoethylene

2,3-diaminomaleonitrile

Downstream raw materials:

tris(1-phenyl-3-methyl-4-(isobutyl-1-one)-5-pyrazolonate)-terbium-(pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile)

[Cu(SCN)(triphenylphosphine)([2,3-f]pyrazino-1,10-phenenthroline-2,3-dicarbonitrile)]

[CuI(triphenylphosphine)([2,3-f]pyrazino-1,10-phenenthroline-2,3-dicarbonitrile)]*MeCN

Refernces

• 1、 Shahroosvand, Hashem,Eskandari, Mortaza. "Ultrafast interfacial charge transfer from the LUMO+1 in ruthenium(II) polypyridyl quinoxaline-sensitized solar cells". . p. 561 - 576. Retrieved 2018.
• 2、 Shahroosvand, Hashem,Rezaei, Shiva,Mohajerani, Ezeddin,Mahmoudi, Malek. "Toward white electroluminescence by ruthenium quinoxaline light emitting diodes". . p. 3035 - 3042. Retrieved 2015.