5699-00-3

Usage

Uses

Used in Chemical Synthesis:
Acenaphthene-5,6-dicarboxylic anhydride is used as an intermediate for the synthesis of 3,5,6-Tribromo-1,2-dihydroacenaphthylene (T771875), a compound derived from Acenaphthene (1,2-Dihydro Acenaphthylene). This synthesis is important for the development of new compounds with potential applications in various industries.
Used in Pharmaceutical Research:
Acenaphthene-5,6-dicarboxylic anhydride and its derivatives may be used as a starting point for the development of new pharmaceutical compounds, particularly in the field of oncology. Acenaphthene-5,6-dicarboxylic anhydride's structural properties make it a promising candidate for further research and development.
Used in Environmental and Industrial Applications:
As a component of polycyclic aromatic hydrocarbons, Acenaphthene-5,6-dicarboxylic anhydride may also have applications in environmental monitoring and industrial processes, where understanding the properties and behavior of these compounds is crucial for safety and efficiency.

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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%.

ACENAPHTHYLENE IMIDE-DERIVED SEMICONDUCTORS

Novel acenaphthylene imide-derived semiconductor materials, including small molecule compounds, polymers and oligomers. Also provided are methods for making the novel semiconductor materials and the use of the novel semiconducting materials in electronic or optoelectronic device. In some embodiments, the novel semiconducting materials are used as n-channel component in organic field-effect transistors as well as complementary electronic circuits including inverters. High mobility can be achieved.

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

Linear and star-shaped naphthalimide-fused pyrazinacenes

A novel naphthalimide derivative endowed with a diketone functionality has been synthesized and used to develop a family of highly symmetric, flat, n-type semiconducting naphthalimide-based pyrazinacenes. By changing the symmetry of these compounds and the number of naphthalimide constituents, fine tuning of their electrochemical, photophysical, and morphological properties is achieved.

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).

Reactions of 5,6-Dilithioacenaphthene-N,N,N',N'-Tetramethyl-1,2-ethanediamine Complex with α-Diketones. I. cis-Directing 1:1 Cyclic Additions with Acyclic and Cyclic α-Diketones and Related Compounds

The title complex (3) is readily generated from 5,6-dibromoacenaphthene with butyllithium and the diamine in ether at -10-0 deg C.The reaction of 3 with biacetyl gave cis-1,2,5,6-tetrahydro-1,2-dimethylcyclopent-acenaphthylene-1,2-diol but no trans-isomer, whereas the reaction of pyracenequinone (PYQ) with methylmagnesium bromide gave both the cis- and trans-diols.The reactions of 3 with acenaphthenequinone and PYQ also gave cis-diols.On treatment with phenylboronic, these cis-diols quantitatively yielded the corresponding cyclic esters.The diols and their derivatives tend to form crystalline molecular compounds with solvent molecules.The stereoselectivity of the cyclic addition between 3 and the acyclic α-diketone can be best explained in terms of five-membered chelate-ring formation in a transition state.