227-09-8

Basic information

• Product Name: 1,2:8,9-DIBENZOPENTACENE
• Synonyms: 1,2,8,9-DIBENZOPENTACENE;1,2:8,9-DIBENZOPENTACENE;DIBENZO-(A,L)PENTACENE;1,2,8,9-Dibenzpentacene;1,2:8,9-Dibenzpentacene;Dibenzo(a1)pentacene;Dibenzo-1,2,8,9-pentacene;Dibenzopentacene
• CAS NO: 227-09-8
• Molecular Formula: C₃₀H₁₈
• Molecular Weight: 378.46
• EINECS: 205-933-9
• Mol File: 227-09-8.mol

Chemical Properties

• Boiling Point: 677 °C at 760 mmHg
• Flash Point: 360.6 °C
• Appearance: /
• Density: 1.286 g/cm³
• Vapor Pressure: 2E-17mmHg at 25°C
• Refractive Index: 1.867
• CAS DataBase Reference: 1,2:8,9-DIBENZOPENTACENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:8,9-DIBENZOPENTACENE(227-09-8)
• EPA Substance Registry System: 1,2:8,9-DIBENZOPENTACENE(227-09-8)

Safety Data

• Hazardous Substances Data: 227-09-8(Hazardous Substances Data)

Usage

Uses

Used in Electronics Industry:
1,2:8,9-Dibenzopentacene is used as a semi-conducting material for its exceptional photophysical properties, making it suitable for applications in organic light-emitting diodes (OLEDs). These diodes are known for their high efficiency, low power consumption, and thin, flexible design, which are crucial for the development of advanced electronic devices.
1,2:8,9-Dibenzopentacene is also used as a component in organic field-effect transistors (OFETs), which are essential for the construction of flexible and lightweight electronic circuits. OFETs are used in a variety of applications, including displays, sensors, and radio frequency identification (RFID) tags.
In the field of renewable energy, 1,2:8,9-Dibenzopentacene is used as a component in organic photovoltaics (OPVs). These solar cells have the potential to offer a more sustainable and cost-effective alternative to traditional silicon-based solar panels, with the added benefits of being lightweight and flexible.
Used in Research and Development:
1,2:8,9-Dibenzopentacene is primarily used for research purposes, where its unique properties are explored and harnessed for the development of new materials and technologies. This includes studying its potential applications in various industries and understanding its environmental and health impact to ensure safe and responsible use.

InChI:InChI=1/C30H18/c1-3-7-27-19(5-1)9-11-21-13-23-16-26-18-30-22(12-10-20-6-2-4-8-28(20)30)14-24(26)15-25(23)17-29(21)27/h1-18H

Synthetic route

8,17-dihydro-8,17-methanodibenzo[a,l]pentacen-19-one → 1,2:8,9-dibenzopentacene (227-09-8)

Conditions	Yield
In neat (no solvent) at 200℃; for 0.25h; Inert atmosphere;	100%

1,3-bis-(2-methyl-[1]naphthoyl)-benzene → 1,2:8,9-dibenzopentacene (227-09-8) + dibenzo[c,m]dibenzo[d,d’]phenanthrene (222-51-5)

Conditions	Yield
Erhitzen auf Siedetemperatur unter Abdestillieren des entstehenden Wassers;

1,4-bis-(2-methyl-[1]naphthoyl)-benzene → 1,2:8,9-dibenzopentacene (227-09-8) + dibenzo[c,m]dibenzo[d,d’]phenanthrene (222-51-5)

Conditions	Yield
Erhitzen auf Siedetemperatur unter Abdestillieren des entstehenden Wassers;

1.3-bis-<2-methyl-naphthoyl-(1)>-benzene → 1,2:8,9-dibenzopentacene (227-09-8) + dibenzo[c,m]dibenzo[d,d’]phenanthrene (222-51-5)

1.4-bis-<2-methyl-naphthoyl-(1)>-benzene → 1,2:8,9-dibenzopentacene (227-09-8) + dibenzo[c,m]dibenzo[d,d’]phenanthrene (222-51-5)

7.9.16.18-tetraoxo-7.9.16.18-tetrahydro-dibenzopentacene → 1,2:8,9-dibenzopentacene (227-09-8) + 8,17-dihydro-dibenzo[a,l]pentacene

Conditions	Yield
With sodium chloride; zinc(II) chloride; zinc at 210 - 310℃;

dibenzo[a,l]pentacene-7,9,16,18-tetraone (81682-86-2) + zinc-powder + NaCl + ZnCl2 → 1,2:8,9-dibenzopentacene (227-09-8) + 8,17-dihydro-dibenzo[a,l]pentacene

Conditions	Yield
at 310℃;

19,19-dimethoxy-8,17-dihydro-8,17-methanodibenzo[a,l]pentacene → 1,2:8,9-dibenzopentacene (227-09-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: trimethylsilyl iodide / dichloromethane / 3 h / 20 - 45 °C / Schlenk technique; Inert atmosphere 2: neat (no solvent) / 0.25 h / 200 °C / Inert atmosphere View Scheme

maleic anhydride (108-31-6) + 1,2:8,9-dibenzopentacene (227-09-8) → (+/-)-8,17-dihydro-8,17-ethano-dibenzo[a,l]pentacene-19r,20c-dicarboxylic acid-anhydride

Conditions	Yield
With 1,2,4-Trimethylbenzene

1,2:8,9-dibenzopentacene (227-09-8) → dibenzo[a,l]pentacene-8,17-dione (65492-98-0)

Conditions	Yield
With air; xylene Einwirkung von Sonnenlicht;
With selenium(IV) oxide; nitrobenzene

maleic anhydride (108-31-6) + 1,2:8,9-dibenzopentacene (227-09-8) → C34H20O3

Conditions	Yield
In various solvent(s) at 91.5℃; Mechanism; Rate constant; analogous reaction of other polycyclic aromatic hydrocarbons; structure/reactivity correlations, application of theoretical models;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,7,8-tetrachlorodibenzofuran (58802-20-3)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 2,4,6,8-tetrachlorodibenzofuran (58802-19-0)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 2,3,7,8-Tetrachlorodibenzofuran (51207-31-9)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,4-tetrachlorodibenzofuran (24478-72-6)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,4-tetrachloronaphthalene (20020-02-4)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,3,5,8-tetrachloronaphthalene (31604-28-1)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,5-tetrachloronaphthalene (53555-63-8)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,4-trichloronaphthalene (50402-51-2)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3-trichloro-naphthalene (50402-52-3)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,6-trichloronaphthalene (51570-44-6)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,4,6,7-tetrachloronaphthalene (55720-43-9)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,7-trichloronaphthalene (55720-34-8)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,6,7-trichloronaphthalene (55720-39-3)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,5-trichloronaphthalene (55720-33-7)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,8-trichloronaphthalene (55720-35-9)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,3,6,7-tetrachloronaphthalene (55720-42-8)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,7-Tetrachloronaphthalene (55720-41-7)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,4,6-tetrachloronaphthalene (51570-45-7)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,5,7-pentachloronaphthalene (53555-65-0)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,5,7-tetrachloro-naphthalene (67922-23-0)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,4,8-tetrachloronaphthalene (6529-87-9)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,4,7-tetrachloronaphthalene (67922-21-8)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,5,6-tetrachloronaphthalene (67922-22-9)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,4,6-Pentachloronaphthalene (67922-26-3)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

Upstream product

• 81682-86-2 dibenzo[a,l]pentacene-7,9,16,18-tetraone 

Downstream Products

• 58802-20-3 1,2,7,8-tetrachlorodibenzofuran 
• 58802-19-0 2,4,6,8-tetrachlorodibenzofuran 
• 24478-72-6 1,2,3,4-tetrachlorodibenzofuran 
• 20020-02-4 1,2,3,4-tetrachloronaphthalene 
• 31604-28-1 1,3,5,8-tetrachloronaphthalene 
• 53555-63-8 1,2,3,5-tetrachloronaphthalene 
• 51570-44-6 1,2,6-trichloronaphthalene 
• 55720-43-9 1,4,6,7-tetrachloronaphthalene 
• 55720-39-3 2,3,5-trichloronaphthalene 
• 55720-33-7 1,2,5-trichloronaphthalene 
• 55720-35-9 1,2,8-trichloronaphthalene 
• 55720-42-8 1,3,6,7-tetrachloronaphthalene 
• 55720-41-7 1,2,3,7-tetrachloronaphthalene 
• 53555-65-0 1,2,3,5,7-pentachloronaphthalene 

Relevant articles and documents

A Practical General Method for the Preparation of Long Acenes

The field of long acenes, the narrowest of the zig-zag graphene nanoribbons, has been an area of significant interest in the past decade because of its potential applications in organic electronics, spintronics and plasmonics. However the low solubility and high reactivity of these compounds has so far hindered their preparation on large scales. We report here a concise strategy for the synthesis of higher acenes through Diels–Alder condensation of arynes with a protected tetraene ketone. After deprotection by cleavage of the ketal, the obtained monoketone precursors cleanly yield the corresponding acenes through quantitative cheletropic thermal decarbonylation in the solid state, at moderate temperatures of 155 to 205 °C. This approach allows the preparation of heptacene, benzo[a]hexacene, cis- and trans-dibenzopentacene and offers a valuable new method for the synthesis of even larger acenes.