Dibenzo[h,rst]pentaphene

Base Information

• Chemical Name: Dibenzo[h,rst]pentaphene
• CAS No.: 192-47-2
• Molecular Formula: C28H16
• Molecular Weight: 352.44
• Hs Code.: 2902909090
• UNII: HO4PC996HF
• DSSTox Substance ID: DTXSID6074831
• Nikkaji Number: J34.842B
• Wikidata: Q26840826
• Mol file: 192-47-2.mol

Synonyms:Dibenzo[h,rst]pentaphene;192-47-2;Tribenzo(a,e,i)pyrene;DIBENZO(H,RST)PENTAPHENE;1,2:4,5:7,8-Tribenzpyrene;BRN 2058374;1,2:4,5:8,9-Tribenzopyrene;HO4PC996HF;4-05-00-02891 (Beilstein Handbook Reference);heptacyclo[14.10.2.02,7.08,28.010,15.019,27.020,25]octacosa-1(26),2,4,6,8,10,12,14,16(28),17,19(27),20,22,24-tetradecaene;dibenzo[h,rst]pentaphane;UNII-HO4PC996HF;DTXSID6074831;CHEBI:82441;(1,2:4,5:7,8)-Tribenzopyrene;DIBENZO(H,RST)PENTAPHENE [IARC];LS-61135;C19392;Q26840826

Chemical Property of Dibenzo[h,rst]pentaphene

Chemical Property:

• Vapor Pressure: 4.58E-15mmHg at 25°C
• Melting Point: 334.85°C
• Refractive Index: 1.8430 (estimate)
• Boiling Point: 629.3°Cat760mmHg
• Flash Point: 330.5°C
• PSA: 0.00000
• Density: 1.333g/cm³
• LogP: 8.04360
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 352.125200510
• Heavy Atom Count: 28
• Complexity: 541

Purity/Quality:

98%,99%, ^*data from raw suppliers

DIBENZO[H,RST]PENTAPHENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C3=C4C(=CC2=C1)C5=CC=CC=C5C6=CC7=CC=CC=C7C(=C64)C=C3
• General Description: Dibenzo[h,rst]pentaphene is a polycyclic aromatic hydrocarbon (PAH) with potential applications as an organic semiconductor due to its hole-transporting properties, making it suitable for use in organic field-effect transistors (OFETs). It can be synthesized through a chemoselective C-O arylation process involving dimethoxyanthraquinones and arylboronates, followed by further transformations. Dibenzo[h,rst]pentaphene is also known by alternative names such as 1,2:4,5:7,8-Tribenzpyrene, 1,2:4,5:8,9-Tribenzopyrene, and Tribenzo[a,e,i]pyrene.

Technology Process of Dibenzo[h,rst]pentaphene

There total 15 articles about Dibenzo[h,rst]pentaphene 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: 43.0%

2,2'-(anthracene-1,4-diyl)dibenzaldehyde → 1.2,4.5,8.9-tribenzopyrene (192-47-2)

Guidance literature:

With tin(II) chloride dihdyrate; sulfuric acid; In dichloromethane; isopropyl alcohol; at 20 ℃; for 18h; Darkness;

DOI:10.1021/acs.orglett.9b04382

Reference yield:

1,4-diamino-9,10-anthraquinone (128-95-0) → 1.2,4.5,8.9-tribenzopyrene (192-47-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 5 h / 20 - 65 °C

2.1: sodium tetrahydroborate; isopropyl alcohol / 4 h / 20 °C / Cooling with ice

2.2: 4 h / Reflux

3.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; methanol; water / 16 h / Reflux; Inert atmosphere

4.1: sulfuric acid; tin(II) chloride dihdyrate / dichloromethane; isopropyl alcohol / 18 h / 20 °C / Darkness

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; tin(II) chloride dihdyrate; sulfuric acid; potassium carbonate; isopropyl alcohol; copper(ll) bromide; In methanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; 3.1: |Suzuki Coupling;

DOI:10.1021/acs.orglett.9b04382

Reference yield:

1,4-dibromoanthracene-9,10-dione (85392-80-9) → 1.2,4.5,8.9-tribenzopyrene (192-47-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate; isopropyl alcohol / 4 h / 20 °C / Cooling with ice

1.2: 4 h / Reflux

2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; methanol; water / 16 h / Reflux; Inert atmosphere

3.1: sulfuric acid; tin(II) chloride dihdyrate / dichloromethane; isopropyl alcohol / 18 h / 20 °C / Darkness

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tin(II) chloride dihdyrate; sulfuric acid; potassium carbonate; isopropyl alcohol; In methanol; dichloromethane; water; isopropyl alcohol; toluene; 2.1: |Suzuki Coupling;

DOI:10.1021/acs.orglett.9b04382

upstream raw materials:

dibenzo[a,h]anthracene

9,10-dibenzyl-1,2,3,4,5,6,7,8-octahydro-anthracene

picene

benzene

Downstream raw materials:

6,7-Benzopentaphen

Refernces

Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C-O Arylation of Dimethoxyanthraquinones

10.1021/acs.orglett.7b01666

This research describes a convenient method for synthesizing dibenzo[h,rst]pentaphenes and dibenzo[fg,qr]pentacenes, which are polycyclic aromatic hydrocarbons (PAHs) with potential applications as organic semiconductors. The process involves ruthenium-catalyzed chemoselective C?O arylation of dimethoxyanthraquinones with arylboronates, leading to diarylation products that can be further transformed into the target PAHs through a two-step procedure consisting of a Corey?Chaykovsky reaction and subsequent dehydrative aromatization. The synthesized compounds were found to exhibit hole-transporting characteristics, making them suitable for use in organic field-effect transistors (OFETs). Key chemicals used in the process include 1,4- and 1,5-dimethoxyanthraquinones, arylboronates, trimethylsulfonium iodide, sodium hydride, and various Lewis acid catalysts such as InCl3 and SnCl2.