214-63-1

Basic information

• Product Name: Dibenzo[de,mn]naphthacene
• Synonyms: Dibenzo[de,mn]naphthacene;Zethrene
• CAS NO: 214-63-1
• Molecular Formula: C24H14
• Molecular Weight: 302.37
• Mol File: 214-63-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 262 °C
• Boiling Point: 582.8±40.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Dibenzo[de,mn]naphthacene(CAS DataBase Reference)
• NIST Chemistry Reference: Dibenzo[de,mn]naphthacene(214-63-1)
• EPA Substance Registry System: Dibenzo[de,mn]naphthacene(214-63-1)

Safety Data

• Hazardous Substances Data: 214-63-1(Hazardous Substances Data)

Upstream product

• 2435-82-7 2H,2'H-[1,1']biacenaphthylenylidene 
• 83-32-9 acenaphthene 
• 208-96-8 acenaphthylene 
• 27286-74-4 1-(Trimethylsilylethinyl)-8-(1'-iod-8'-naphthylethinyl)naphthalin 
• 64-17-5 ethanol 
• 111698-26-1 7,7a-dihydrodibenzonaphthacene 
• 32659-60-2 3,4,16,17-Tetraphenylheptacyclo<17.7.1.1^6,10.0^2,5.0^14,28.0^15,18.0^23,27>-octacosa-1(26),6,8,10(28),11,13,19,21,23(27),24-decaen 
• 7446-70-0 aluminium trichloride 
• 2025-95-8 1,8-bis(bromomethyl)naphthalene 
• 192384-39-7 1-iodo-8-(trimethylsilylethynyl)naphthalene 
• 17935-66-9 1,8-divinylnaphthalene 
• 1730-04-7 1,8-diiodonaphthalene 
• 75-05-8 acetonitrile 
• 17216-14-7 naphthalene-1,8-dicarbaldehyde 

Relevant articles and documents

Revisiting zethrene: Synthesis, reactivity and semiconductor properties

Zethrene, a unique polycyclic aromatic hydrocarbon with formally fixed C-C double bonds, is predicted to have interesting properties and potential applications as an optical and electronic material. Here we report a novel synthesis of zethrene with improved yield, which presumably involves dinaphtho[10]-annulene as an unstable intermediate. With this convenient access to zethrene, we used zethrene as a p-type semiconductor in thin film transistors for the first time. It is found that Diels-Alder addition to the bay region of zethrene leads to new derivatives of benzo[pqr]naphtho[8,1,2-bcd]perylene, which behave as n-type organic semiconductors.

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Synthesis, structure, and photophysical properties of dibenzo-[de, mn]naphthacenes

Zethrenes were synthesized by Pd-catalyzed cyclodimerization of 1-ethynyl-8-iodonaphthalenes. The structure of these cycloadducts was confirmed by X-ray crystal analysis. The bond lengths and bond alternation in the crystal structures reveal that the central two six-membered rings of the title compounds lack aromaticity.

Synthesis of Potentially Basic Hydrocarbons by Sulphur Extrusion and/or Bis-Wittig Reactions. Two Syntheses of Benzindenophenalene and a New Synthesis of Dibenzonaphthacene (Zethrene)

Macrocyclic bis-sulphides have been prepared from 1,2-, 2,3-, and 1,8-bis(bromomethyl)naphthalenes.Methylation of the bis-sulphides, followed by the Stevens rearrangement, gave the corresponding carbocycles with extra-annular sulphide groups; removal of these sulphide groups by Hofmann elimination led to spontaneous trans-annular condensation.Using this general method, two hydrocarbons were synthesized: benzindenophenalene and dibenzonaphthacene (or zethrene).An alternative synthetic route led to the synthesis of benzindenophenalene, using the Wittig reaction between naphthalene-2,3-carbaldehyde and 1,8-bis(triphenylphosphoniomethyl)naphthalene dibromide.