5699-00-3

Basic information

• Product Name: Acenaphthene-5,6-dicarboxylic anhydride
• Synonyms: Acenaphthene-5,6-dicarboxylic anhydride;1,2-Dihydro-6-oxa-cyclopenta[cd]phenalene-5,7-dione;6,7-Dihydroacenaphtho[5,6-cd]pyran-1,3-dione
• CAS NO: 5699-00-3
• Molecular Formula: C₁₄H₈O₃
• Molecular Weight: 224.21
• Mol File: 5699-00-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Solubility: Chloroform
• CAS DataBase Reference: Acenaphthene-5,6-dicarboxylic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Acenaphthene-5,6-dicarboxylic anhydride(5699-00-3)
• EPA Substance Registry System: Acenaphthene-5,6-dicarboxylic anhydride(5699-00-3)

Safety Data

• Hazardous Substances Data: 5699-00-3(Hazardous Substances Data)

Usage

Uses

6,7-Dihydroacenaphtho[5,6-cd]pyran-1,3-dione is an intermediate in synthesizing 3,?5,?6-?Tribromo-?1,?2-?dihydroacenaphthylene (T771875), a derived from Acenaphthene (1,2-Dihydro Acenaphthylene) (D448330), which is a polycyclic aromatic hydrocarbons as carcinogenic agents.

Upstream product

• 5698-99-7 5,6-acenaphthenedicarboxylic acid 
• 87985-99-7 2-diazo-5,6-dihydrocyclopentacenaphthylen-1-one 
• 5254-01-3 1,2-diketopyracene 
• 98361-87-6 5,6-dihydrocyclopentacenaphthylene-1,2-dione mono-p-toluenesulfonylhydrazone 
• 31458-06-7 N⁵,N⁵,N⁶,N⁶-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide 
• 83-32-9 acenaphthene 
• 19190-91-1 5,6-dibromoacenaphthene 

Downstream Products

• 4599-96-6 Acenaphthen-5,6-dicarbonsaeure-dimethylester 
• 77989-03-8 Acenaphthen-5,6-dicarbonsaeure-N-(p-nitro-phenyl)-imid 
• 5699-11-6 Acenaphthen-5,6-dicarbonsaeure-N-amino-imid 
• 4599-95-5 5,6-bis(bromomethyl)acenaphthene 
• 92964-95-9 dimethyl acenaphthylene-4,5-dicarboxylate 

Relevant articles and documents

Synthesis, crystal structure, and application of an acenaphtho[1,2-k] fluoranthene diimide derivative

Organic electron acceptor materials play an important role in organic electronics. Recently, many organic electron acceptors have been developed, in which aromatic fused-imides have proved to be a promising family of excellent electron acceptors. We report the first synthesis of a novel aromatic fused-imide, acenaphtho[1, 2-k]fluoranthene diimide derivative (AFI), using lithium-halogen exchange and Diels-Alder reactions. The construction of a large conjugated plane and the introduction of electron-withdrawing imide groups endow AFI with a low lowest unoccupied molecular orbital (LUMO) level of -3.80 eV. AFI exhibits a regular molecular arrangement and strong ??-?? interactions in the single-crystal structure, which indicates its potential application in organic electronic devices. Solar cell devices that were fabricated using AFI as the electron acceptor and P3HT as the electron donor achieved an energy conversion efficiency of 0.33%.

Tetraazabenzodifluoranthene diimides: Building blocks for solution-processable n-type organic semiconductors

11-Ring heterocyclic diimides were synthesized and found to be planar and to exhibit a slipped face-to-face πstacking. Variation of the substituents tunes the electronic structure and properties. In n-channel organic field-effect transistors, the new organic semiconductors have a high electron mobility. When they were used as acceptor material in polymer solar cells, a power conversion efficiency of 1.8 % was obtained. Copyright

Mechanistic Studies on the Wolff Rearrangement: The Chemistry and Spectroscopy of Some α-Ketocarbenes

Photochemical extrusion of dinitrogen from diazo ketones 1-4 matrix isolated in argon at 10-15 K produces α-ketocarbenes 5, 6, and 8.UV-vis, infrared, and electron spin resonance spectroscopy identify the α-ketocarbenes, which are further characterized by trapping with carbon monoxide and dioxygen.Excitation (T0-T1) of the α-ketocarbenes leads to rapid ring contraction of 5 -> 9 and slow ring contraction of 6 -> 10 and 8 -> 12.This trend parallels the increasing degree of strain in the product ketenes.Shorter wavelength irradiation causes rapid ring contraction of 6 -> 10 and 8 -> 12.The stepwise Wolff rearrangement of 1-4 proceeds through an α-ketocarbene.Ring contraction occurs in a singlet excited state (S''') formed upon photolysis of the primary product α-ketocarbene (T0).