53397-65-2

Usage

Uses

Used in Polymer Chemistry:
5,6,11,12-Tetradehydrodibenzo[a,e]cyclooctene is used as a reagent for the efficient preparation of polymer dimers. Its application in this field is due to its ability to facilitate the formation of dimeric structures, which are essential in various polymer-related processes and applications.
In the Polymer Industry:
5,6,11,12-Tetradehydrodibenzo[a,e]cyclooctene is used as a key component in the synthesis of polymer dimers for enhancing the properties of polymers. The use of 5,6,11,12-Tetradehydrodibenzo[a,e]cyclooctene in the polymer industry is aimed at improving the overall performance of the resulting polymers, such as their strength, flexibility, and durability.

InChI:InChI=1/C16H8/c1-2-6-14-11-12-16-8-4-3-7-15(16)10-9-13(14)5-1/h1-8H

Upstream product

• 53334-12-6 5,6,11,12-Tetrabromo-5,6,11,12-dihydrodibenzocyclooctene 
• 91861-63-1 5,6,11,12-Tetrabromdibenzocycloocten 
• 468751-38-4 ortho-(phenylsulfonylmethyl)benzaldehyde 
• 468751-39-5 5,11-bis-benzenesulfonyl-dibenzo[a,e]cyclooctene 
• 262-89-5 dibenzo[a,e]cyclooctatetraene 
• 1460-59-9 5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene 
• 94275-22-6 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctadiene 
• 53334-15-9 5,6-dibromo-5,6-dihydrodibenzocyclo-octene 
• 53397-66-3 5,6-didehydrodibenzocyclo-octene 
• 82651-72-7 ortho-(phenylsulfonylmethyl)benzonitrile 
• 468751-39-5 5,11-bis(phenylsulfonyl)dibenzo[a,e][8]annulene 
• 22115-41-9 2-(bromomethyl)benzonitrile 
• 2042-37-7 o-cyanobromobenzene 
• 91-13-4 α,α'-dibromo-o-xylene 

Downstream Products

• 85135-51-9 C₄₂H₂₈N₄ 
• 1460-59-9 5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene 
• 196311-55-4 9,14,23,28-tetraphenyldiphenanthro[9,10-b:9',10'-n]tetraphenylene 
• 506442-12-2 C₄₈H₃₂N₄O₄ 
• 506442-14-4 C₅₀H₃₀N₂O₂ 
• 198979-18-9 [(Ph₃P)2Pt](5,5,16,16-tetramethyl-5,16-didehydro-5,16-disiladibenzo[a,e]naphtho[c]cyclooctene) 
• 171909-67-4 5,5,10,10,15,15,20,20-octamethyl-5,10,15,20-tetrahydro-5,10,15,20-tetrasiladibenzo[b,n]tetraphenylene 
• 1116681-31-2 C₂₆H₂₈O 
• 1116681-26-5 C₂₇H₂₃ClO 
• 1116681-27-6 C₂₇H₂₃NO₃ 
• 1116681-25-4 C₂₇H₂₄O 
• 1116681-34-5 C₂₇H₂₂O 
• 1116681-33-4 C₂₄H₁₈O 
• 1116681-32-3 C₂₅H₂₀O 

Relevant academic research and scientific papers

Transient protection of strained alkynes from click reaction via complexation with copper

A transient protection method of cyclooctynes from a click reaction with an azide through 1:1 complexation with a cationic copper(I) salt is reported. The application of the method to a cyclooctyne bearing a terminal alkyne enabled the selective copper-catalyzed click conjugation with an azide at the terminal alkyne moiety, which made cyclooctyne derivatives readily accessible.

Synthesis and properties of 1,6,7,12,13,18,19,24- octamethylacenaphthyleno[b,l]tetraphenylene

The X-ray crystal structure and photophysical properties of 1,6,7,12,13,18,19,24-octamethylacenaphthyleno[b,l]tetraphenylene, which has been synthesized via a Diels-Alder reaction of 5,6,11,12-tetradehydrodibenzo[a,e] cyclooctene and 6,7-dihydro-6-hydroxy-7,9-dimethyl-8H-cyclopenta[a] acenaphthylene-8-one, are reported.

Preparation and crystal structure of a 1:1 inclusion compound of 1,4,11,14-tetramethoxy-dibenzo[b,n]tetraphenylene with pyridine

The new host 1,4,11,14 tetramethoxy-dibenzo[b,n]tetraphenylene forms a 1:1 inclusion compound with pyridine, in which a pair of centrosymmetrically-related guest species are enclosed in the cage surrounded by six host molecules. C36H28O4·C5H5N, Fw = 603.68, triclinic, space group P-1, a = 11.796(2), b = 16.075(3), c = 9.004(2) A?; α = 98.39(3)°, β = 90.01(3)°, γ = 108.19(3)°, V = 1602.8(5) ,A?3, Z = 2, F(000) = 636, Dc = 1.251 g/cm3, μ = 0.080 mm-1. The final R indices [I > 2σ(I)] R1 = 0.0759, wR2 = 0.1970 for 5623 MoKα observed data.

Sequential Photochemistry of Dibenzo[a,e]dicyclopropa[c,g][8]annulene-1,6-dione: Selective Formation of Didehydrodibenzo[a,e][8]annulenes with Ultrafast SPAAC Reactivity

An order of magnitude difference in photoreactivity between bis- (photo-DIBOD, 1) and mono-cyclopropenone-caged dibenzocyclooctadiynes (MC-DIBOD, 5) allows for selective monodecarbonylation of 1. Alternatively, 5 is prepared by selective mono-cyclopropanation of dibenzo[a,e]cyclooctadiyne (DIBOD). MC-DIBOD (5) permits efficient sequential SPAAC cross-linking of azide-derivatized substrates. Cycloaddition to 5 converts an azide moiety into a photocaged form of triazole-fused dibenzo[a,e]cyclooctyne (3). While the azide reactivity of MC-DIBOD (5) and DIBOD is similar to that of other dibenzocyclooctynes, fusion of triazole to the dibenzocyclooctyne system in 3 results in a 3 orders of magnitude enhancement in SPAAC rates. In methanol, 3 reacts with butyl azide at an astonishing rate of 34 M-1 s-1, thus representing the most reactive cyclooctyne analogue reported so far. MC-DIBOD (5) was utilized in the preparation of mixed bis-triazoles and derivatization of the protein BSA with fluorescent dye and polyethylene glycol.

METHODS AND REAGENTS FOR CROSS-LINKING CELLULAR DNA AND RNA VIA STRAIN-PROMOTED DOUBLE-CLICK REACTIONS

The present invention relates to new reagents and methods for modifying nucleic acids where an azide-containing nucleoside or nucleotide derivative is applied to living cells followed by a nitrogenous derivative of dibenzo-1,5-cyclooctadiyne (CODY). The azide- containing derivative is metabolically incorporated into cellular DNA and/or RNA, and the CODY derivative undergoes a strain-promoted double-click reaction to give nucleic acid – nucleic acid cross links, and/or optionally, in the presence of an exogenously added azide (X- N3); to give nucleic acid – "X" cross links.

A visible-light photoactivatable di-nuclear PtIV triazolato azido complex

A novel PtIV triazolato azido complex [3]-[N1,N3] has been synthesised via a strain-promoted double-click reaction (SPDC) between a PtIV azido complex (1) and the Sondheimer diyne (2). Photoactivation of [3]-[N1,N3] with visible ligh

MULTICYCLIC AROMATIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME

The present specification describes a multicyclic aromatic ring compound having a novel structure and an organic light emitting device using the same.

Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): A photoactivatable linchpin for efficient SPAAC crosslinking

The first fully conjugated bis-cyclopropenone (photo-DIBOD), a derivative of dibenzo[a,e][8]annulene, has been synthesized. 350-420 nm irradiation of this robust compound results in the efficient formation of dibenzo [a,e] cyclooctadiyne, an unstable, but

Substituted 5,6,11,12-tetradehydrodibenzo[ a, e ]cyclooctenes: Syntheses, properties, and DFT studies of substituted sondheimer-wong diynes

Highly strained cyclic acetylenes 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes (Sondheimer-Wong diynes) having various substituents on their benzene rings were synthesized successfully by one-pot treatment of the corresponding formyl sulfones with diethyl chlorophosphate/lithium hexamethyldisilazide (LiHMDS) and then lithium diisopropylamide (LDA). When mixtures of two types of formyl sulfones bearing different substituents were subjected to this protocol, the unsymmetrically substituted Sondheimer-Wong diynes could be synthesized in a stepwise manner by isolation of the heterocoupled vinyl sulfone intermediates followed by their treatment with LDA. The UV-vis absorption spectra and cyclic voltammograms of the substituted Sondheimer-Wong diynes were recorded. The electronic effect of substituents on the diynes was investigated in their click reactions and nucleophilic and electrophilic additions.

Dihalo-substituted dibenzopentalenes: Their practical synthesis and transformation to dibenzopentalene derivatives

Diiodo- and bromo, iodo-substituted dibenzopentalenes were obtained by treatment of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene with I2 and IBr, respectively. These dihalo-substituted pentalenes reacted with terminal ethynes in Sonogashira co