215611-93-1

Basic information

• Product Name: Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile
• Synonyms: Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile;REF DUPL: PPDN;2,3-Dicarbonitrilopyrazino[2,3-f][1,10]phenanthroline;2,3-Dicyanodipyrido[3,2-f:2',3'-h]quinoxaline;PPDN , Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitril
• CAS NO: 215611-93-1
• Molecular Formula: C₁₆H₆N₆
• Molecular Weight: 282.265
• EINECS: 200-110-4
• Mol File: 215611-93-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: >250 °C(Solv: ethanol (64-17-5))
• Boiling Point: 654.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.54
• Storage Temp.: 2-8°C
• PKA: -5.11±0.50(Predicted)
• CAS DataBase Reference: Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile(215611-93-1)
• EPA Substance Registry System: Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile(215611-93-1)

Safety Data

• Hazardous Substances Data: 215611-93-1(Hazardous Substances Data)

Usage

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.

InChI:InChI: 1S/C16H6N6/c17-7-11-12(8-18)22-16-10-4-2-6-20-14(10)13-9(15(16)21-11)3-1-5-19-13/h1-6H

Upstream product

• 27318-90-7 1,10-phenanthroline-5,6-dione 
• 1187-42-4 diaminomaleonitrile 
• 54848-44-1 1,2-diamino-1,2-dicyanoethylene 
• 28321-79-1 diiminosuccinonitrile 
• 66-71-7 1,10-Phenanthroline 
• 18514-52-8 2,3-diaminomaleonitrile 

Downstream Products

• 1034732-03-0 [2-(3-phenyl-2-ido)phenylpyrazine](6,7-dicyanodipyrido[f,h]quinoxaline)palladium(II) hexafluorophosphate 
• 1352559-13-7 [CuCl(triphenylphosphine)([2,3-f]pyrazino-1,10-phenenthroline-2,3-dicarbonitrile)]*H₂O 
• 1352559-15-9 [CuBr(triphenylphosphine)([2,3-f]pyrazino-1,10-phenenthroline-2,3-dicarbonitrile)]*MeCN 
• 1352559-17-1 [CuI(triphenylphosphine)([2,3-f]pyrazino-1,10-phenenthroline-2,3-dicarbonitrile)]*MeCN 
• 1352559-20-6 [Cu(SCN)(triphenylphosphine)([2,3-f]pyrazino-1,10-phenenthroline-2,3-dicarbonitrile)] 
• 926626-80-4 tris(1-phenyl-3-methyl-4-(isobutyl-1-one)-5-pyrazolonate)-terbium-(pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile) 

Relevant articles and documents

The comparative study of the DNA binding and biological activities of the quaternized dicnq as a dicationic form and its platinum(II) heteroleptic cationic complex

The square-planar heteroleptic Pt(II) coordination compound [Pt(bpy)(dicnq)](NO3)2 (1) and the quaternized dicnq ligand, namely 12,13-dicyano-5,6-dihydrodipyrazino[2,3-f:1′,2′,3′,4′-lmn][1,10]phenanthroline-4,7-diium dibromide (2) (Fig. 1) were synthesized and fully characterized by means of FTIR, NMR, MALDI-TOF MS and the purity was confirmed by CHN analyses. The DNA binding profiles of 1 and 2 were identified in an identical condition. The biological activities of these compounds were investigated by the assays of transcription and replication inhibition, cytotoxic and antimicrobial activity. The result of this study indicates that, both compounds strongly bind to DNA via intercalation but only 1 has a strong nuclease activity. The coordination compound of dicnq (1) binds to the DNA only slightly stronger than the quaternized form of dicnq (2), and is more potent as an inhibitor of transcription and replication and therefore, 1 has more potential as an anticancer agent but the compounds did not show cytotoxic activity against MCF-7 and MDA-MB-231 breast cancer, and DLD-1 colon cancer cell lines it was found that they only had activities against HepG2 liver cancer cell line with following IC50 values; 94.75 and 159.60 μM for 1 and 2, respectively. In addition, tested bacteria are more susceptible to compound 1. These biological activities of 1 may strongly be due to its ability to digest DNA as a chemical nuclease. According to this study, the quaternization of the ligand does not make biologically more active than the coordination compound of the same ligand in this case. The compound (1) is worth further investigation for its antitumor activities.

Evaluation of the potential effectiveness of ruthenium(II) complexes with 2,3-disubtituted pyrazino[2,3-f][1,10]phenanthroline anchors, R2ppl (R = CN, COOH, COOEt, OH) as sensitizers for solar cells

The ligands of type pyrazino[2,3-f][1,10]phenanthroline, R2ppl, with R = CN, COOH, COOEt or OH, were synthesized and used as precursors for obtaining the corresponding series of complexes of type [Ru(dmbpy) 2R2ppl](PF6)2, where dmbpy is 4,4′-dimethyl-2,2′-bipyridine. The compounds were prepared, characterized, and studied by theoretical DFT calculations in order to evaluate their potentiality as dyes in photoelectrochemical cells. The electron acceptor capacity of the R2ppl ligands was evaluated by analyzing parameters such as electrophilicity and charge distribution on the reduced ligand. Additionally, the R substituents on R2ppl were evaluated as anchoring groups, by variables such as highest spin occupied molecular orbital (HSOMO). Finally, the IT parameter was defined and calculated. This is related to the amount of energy that can be delivered to TiO2 from the acceptor anchoring ligand in the thexi state. According to this parameter, the [Ru(dmbpy)2(COOH)2ppl](PF6)2 complex is predicted to have the best response, among the compounds of the series, when used as dye in a solar cell.

COMPLEX COMPRISING A RARE-EARTH METAL ION AND A COMPLEXING MOIETY

-