Hexaazatriphenylenehexacabonitrile

Base Information

• Chemical Name: Hexaazatriphenylenehexacabonitrile
• CAS No.: 105598-27-4
• Molecular Formula: C18N12
• Molecular Weight: 384.278
• Hs Code.: 2933998090
• Mol file: 105598-27-4.mol

Synonyms:Hexaazatriphenylenehexacabonitrile;Dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile;HAT-CN , Dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hex;2,3,6,7,10,11-Hexacyano-1,4,5,8,9,12-hexaazatriphenylene

Chemical Property of Hexaazatriphenylenehexacabonitrile

Chemical Property:

• Melting Point: >500°C
• Boiling Point: 988.7±65.0 °C(Predicted)
• PKA: -22.82±0.50(Predicted)
• PSA: 220.08000
• Density: 1.86
• LogP: 0.74628
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

99.0% ^*data from raw suppliers

Dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile 97% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile, also known as HAT-CN, is one of the members of the 1,4,5,8,9,12-hexaazatriphenylene (HAT) family, which have?an electron-deficient, rigid, planar, aromatic discotic system with an excellent π–π stacking ability. For this reason, HAT-CN finds applications in organic?light-emitting diodes (OLEDs) serving either as the hole-injection layer (HIL) or charge-generation layer (CGL) material.
• Uses: Hole transport layer materials for low voltage top-emitting organic green light emitting devices; a templating material that forces the copper phthalocyanine (CuPc) donor molecule to assume a vertical-standing morphology.

Technology Process of Hexaazatriphenylenehexacabonitrile

There total 5 articles about Hexaazatriphenylenehexacabonitrile 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: 81.0%

hexaketocyclohexane (527-31-1) + diaminomaleonitrile (1187-42-4) → dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (105598-27-4)

Guidance literature:

In acetic acid; for 2h; Heating;

DOI:10.1021/jo00376a036

Reference yield: 77.0%

hexaketocyclohexane (527-31-1) + 2,3-diaminomaleonitrile (18514-52-8) → dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (105598-27-4)

Guidance literature:

hexaketocyclohexane; 2,3-diaminomaleonitrile; In acetic acid; for 2h; Reflux;

With nitric acid; at 100 ℃; for 3h;

DOI:10.1039/c7dt00293a

Reference yield:

hexaazatriphenylene hexacarbonitrile anion radical → dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (105598-27-4)

Guidance literature:

With nitrosonium tetrafluoroborate; In [D₃]acetonitrile; at 24.84 ℃; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/ja309960m

upstream raw materials:

hexaketocyclohexane

diaminomaleonitrile

2,3-diaminomaleonitrile

Downstream raw materials:

hexaazatriphenylenehexacarboxylic acid

hexaazatriphenylenehexacarboxylic acid trianhydride

Refernces

• 1、 Kobylarczyk, Jedrzej,Pinkowicz, Dawid,Srebro-Hooper, Monika,Hooper, James,Podgajny, Robert. "Anion-π recognition between [M(CN)6]3? complexes and HAT(CN)6: structural matching and electronic charge density modification". . p. 3482 - 3491. Retrieved 2017.
• 2、 Zhu, Xiang,Tian, Chengcheng,Veith, Gabriel M.,Abney, Carter W.,Dehaudt, Jérémy,Dai, Sheng. "In Situ Doping Strategy for the Preparation of Conjugated Triazine Frameworks Displaying Efficient CO2 Capture Performance". . p. 11497 - 11500. Retrieved 2016.
• 3、 Bhanvadia, Viraj J.,Patel, Arun L.,Zade, Sanjio S.. "Constructing a self-assembling C3-symmetric covalently linked (fused) donor-acceptor-type molecule containing a hexaazatriphenylene core". . p. 17700 - 17707. Retrieved 2018.
• 4、 Rademacher,Kanakarajan,Czarnik. "Improved synthesis of 1,4,5,8,9,12-hexaazatriphenylenehexacarboxylic acid". . p. 378 - 380. Retrieved 1994.
• 5、 Roussel, Olivier,Kestemont, Gael,Tant, Julien,De Halleux, Veronique,Aspe, Rafael Gomez,Levin, Jeremy,Remacle, Adrienne,Gearba, Iona Raluca,Ivanov, Dimitri,Lehmann, Matthias,Geerts, Yves. "Discotic liquid crystals as electron carrier materials". . p. 35 - 39. Retrieved 2003.
• 6、 Aragay, Gemma,Frontera, Antonio,Lloveras, Vega,Vidal-Gancedo, José,Ballester, Pablo. "Different nature of the interactions between anions and HAT(CN) 6: From reversible anion-π complexes to irreversible electron-transfer processes (HAT(CN)6 = 1,4,5,8,9,12- hexaazatriphenylene)". . p. 2620 - 2627. Retrieved 2013.