5,7-Dihydroindolo[2,3-b]carbazole

Base Information

• Chemical Name: 5,7-Dihydroindolo[2,3-b]carbazole
• CAS No.: 111296-90-3
• Molecular Formula: C18H12 N2
• Molecular Weight: 256.307
• Hs Code.: 2933990090
• European Community (EC) Number: 834-009-3
• DSSTox Substance ID: DTXSID60438284
• Nikkaji Number: J500.827A
• Wikidata: Q72465327
• Mol file: 111296-90-3.mol

Synonyms:5,7-dihydroindolo(2,3-b)carbazole

Chemical Property of 5,7-Dihydroindolo[2,3-b]carbazole

Chemical Property:

• Melting Point: 348-360℃
• Boiling Point: 569.8±23.0 °C(Predicted)
• PKA: 16.70±0.30(Predicted)
• PSA: 31.58000
• Density: 1.404±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 4.95560
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 256.100048391
• Heavy Atom Count: 20
• Complexity: 348

Purity/Quality:

98% ^*data from raw suppliers

5,7-Dihydro-indolo[2,3-b]carbazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=CC4=C(C=C3N2)NC5=CC=CC=C54
• Uses: 5,7-Dihydro-indolo[2,3-b]carbazole could be a useful thermally activated delayed fluorescence (TADF) emitter for making efficient OLEDs.

Technology Process of 5,7-Dihydroindolo[2,3-b]carbazole

There total 15 articles about 5,7-Dihydroindolo[2,3-b]carbazole 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: 91.9%

phenylhydrazine hydrochloride (59-88-1) + 1,4-Cyclohexanedione (637-88-7) → 5,7-dihydroindole-[2,3-b]carbazole (111296-90-3)

Guidance literature:

In diphenylether; decalin; for 0.5h; Reflux;

Reference yield: 90.0%

C18H14Cl2N2 (1613260-57-3) → 5,7-dihydroindole-[2,3-b]carbazole (111296-90-3)

Guidance literature:

With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate; In N,N-dimethyl acetamide; at 140 ℃; for 20h; Inert atmosphere;

DOI:10.1021/ol500663b

Reference yield: 59.0%

2',4'-dinitro-1,1':5',1''-terphenyl (150758-05-7) → 5,7-dihydroindole-[2,3-b]carbazole (111296-90-3)

Guidance literature:

With triethyl phosphite; In various solvent(s); for 48h; Heating;

upstream raw materials:

2',4'-dinitro-1,1':5',1''-terphenyl

m-phenylenediamine

1,5-dibromo-2,4-dinitrobenzene

2-Chlorobenzeneboronic acid

Downstream raw materials:

5,7-bis-(1,1-biphenyl-4-yl)-5,7-dihydroindolo[2,3-b]carbazole

Refernces

• 1、 Knoelker, Hans-Joachim,Reddy, Kethiri R.. "Transition metal complexes in organic synthesis - 44.: Iron-mediated synthesis of indolo[2,3-b]carbazole". . p. 4007 - 4008. Retrieved 1998.
• 2、 Kn?lker, Hans-Joachim,Reddy, Kethiri R.. "Transition metal complexes in organic synthesis. Part 61: Convergent synthesis of indolo[2,3-b]carbazole by an iron-mediated bidirectional annulation of two indole rings". . p. 4733 - 4737. Retrieved 2000.
• 3、 -. "POLYCYCLIC AROMATIC DERIVATIVE COMPOUNDS AND ORGANIC LIGHT-EMITTING ELEMENTS USING THE SAME". Paragraph 0231; 0235-0238. . Retrieved 2020/06/30.
• 4、 -. "POLYCYCLIC AROMATIC COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICES USING THE SAME". Paragraph 0136-0137. . Retrieved 2020/06/29.