1128-13-8

Usage

Uses

Used in Chemical Synthesis:
2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetraaminois used as a key intermediate in the synthesis of various chemical products, leveraging its high reactivity and unique chemical structure.
Used in Chemical Reactions:
2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetraaminois employed as a reagent in chemical reactions, where its versatility and reactivity are essential for achieving desired outcomes in the synthesis process.
Used in Pharmaceutical Industry:
2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetraaminois used as a building block in the development of pharmaceutical compounds, contributing to the creation of new drugs and therapeutic agents.
Used in Research and Development:
In the field of research and development, 2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetraamino- is utilized for studying chemical reactions and exploring new synthetic pathways, further expanding the understanding of organic chemistry and its applications.

Upstream product

• 99054-61-2 2,3,5,6-tetraphthalimido-1,4-benzoquinone 
• 22826-69-3 2.5-Dimethoxy-3.6-diazido-1.4-benzochinon 
• 118-75-2 chloranil 
• 7732-18-5 water 
• 7803-57-8 hydrazine hydrate 
• 7210-71-1 2,5-dichloro-3,6-dimethoxy-1,4-benzoquinone 
• 7510-09-0 2,5-bis-acetylamino-3,6-dichloro-[1,4]benzoquinone 
• 727-90-2 2,5-Bis--3,6-diamino-1,4-benzochinon 

Downstream Products

• 107041-56-5 2,3,6,7-tetraphenyl-1,4,5,8-tetraaza-9,10-anthraquinone 
• 22826-88-6 2,5-Bis-<ω-carboxy-propenoylamino>-3,6-diamino-1,4-benzochinon 
• 22826-81-9 2,5-Di-n-butyrylamino-3,6-diamino-1,4-benzochinon 
• 22826-84-2 2,5-Dilauroylamino-3,6-diamino-1,4-benzochinon 
• 22827-06-1 2,5-Bis-<4-chlor-benzalamino>-3,6-diamino-1,4-benzochinon 
• 22827-05-0 2,5-Bis-<2-chlor-benzalamino>-3,6-diamino-1,4-benzochinon 
• 22826-67-1 2,5-Bis-<2-hydroxy-benzalamino>-3,6-diamino-1,4-benzochinon 
• 22826-89-7 2,5-Bis--3,6-diamino-1,4-benzochinon 
• 22908-95-8 2,5-Bis--3,6-diamino-1,4-benzochinon 
• 22826-76-2 2,5-Bis--3,6-diamino-1,4-benzochinon 
• 22826-75-1 2,5-Bis--3,6-diamino-1,4-benzochinon 
• 22908-89-0 2,5-Diisobutyrylamino-3,6-diamino-1,4-benzochinon 
• 3586-24-1 2,5-Bis--3,6-diamino-1,4-benzochinon 
• 22817-70-5 2,5-Bis-<4-dimethylamino-benzalamino>-3,6-diamino-1,4-benzochinon 

Relevant academic research and scientific papers

A Microporous Covalent–Organic Framework with Abundant Accessible Carbonyl Groups for Lithium-Ion Batteries

A key challenge faced by organic electrodes is how to promote the redox reactions of functional groups to achieve high specific capacity and rate performance. Here, we report a two-dimensional (2D) microporous covalent–organic framework (COF), poly(imide-benzoquinone), via in situ polymerization on graphene (PIBN-G) to function as a cathode material for lithium-ion batteries (LIBs). Such a structure favors charge transfer from graphene to PIBN and full access of both electrons and Li+ ions to the abundant redox-active carbonyl groups, which are essential for battery reactions. This enables large reversible specific capacities of 271.0 and 193.1 mAh g?1 at 0.1 and 10 C, respectively, and retention of more than 86 % after 300 cycles. The discharging/charging process successively involves 8 Li+ and 2 Li+ in the carbonyl groups of the respective imide and quinone groups. The structural merits of PIBN-G will trigger more investigations into the designable and versatile COFs for electrochemistry.

Multi-electron Reduction Capacity and Multiple Binding Pockets in Metal–Organic Redox Assembly at Surfaces

Metal–ligand complexation at surfaces utilizing redox-active ligands has been demonstrated to produce uniform single-site metals centers in regular coordination networks. Two key design considerations are the electron storage capacity of the ligand and the metal-coordinating pockets on the ligand. In an effort to move toward greater complexity in the systems, particularly dinuclear metal centers, we designed and synthesized tetraethyltetra-aza-anthraquinone, TAAQ, which has superior electron storage capabilities and four ligating pockets in a diverging geometry. Cyclic voltammetry studies of the free ligand demonstrate its ability to undergo up to a four-electron reduction. Solution-based studies with an analogous ligand, diethyldi-aza-anthraquinone, demonstrate these redox capabilities in a molecular environment. Surface studies conducted on the Au(111) surface demonstrate TAAQ′s ability to complex with Fe. This complexation can be observed at different stoichiometric ratios of Fe:TAAQ as Fe 2p core level shifts in X-ray photoelectron spectroscopy. Scanning tunneling microscopy experiments confirmed the formation of metal–organic coordination structures. The striking feature of these structures is their irregularity, which indicates the presence of multiple local binding motifs. Density functional theory calculations confirm several energetically accessible Fe:TAAQ isomers, which accounts for the non-uniformity of the chains.

Toward Benzobis(thiadiazole)-based Diradicaloids

We theoretically predicted that acetylene-bridged benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole (BBT) oligomers would show a quick increase of diradical character with the extension of chain length. To validate the hypothesis, six stable BBT-based diradicaloids were synthesized and fully characterized by X-ray crystallographic analysis and various spectroscopic measurements. Three of them showed prominent paramagnetic activity at elevated temperatures due to thermal population from the open-shell singlet ground state to triplet excited state. It was also found that substitution by electron-donating triphenylamine groups at the termini promoted the diradical character and reduced the singlet–triplet energy gap, and at the same time, resulted in intense near-infrared absorption.

Benzoquinone-imidazole hybrids as selective colorimetric sensors for cyanide in aqueous, solid and gas phases

Five new chemosensors (R1-R5), possessing benzoquinone as the signaling unit and imidazole as the H-bond donor unit, for cyanide sensing have been rationally designed, synthesized and characterized by NMR and mass spectroscopy. The structure of R5 was confirmed by single crystal XRD studies. These receptors exhibited a prominent visual colour change toward the cyanide ion over other common anions in an aqueous HEPES buffer-DMF (9:1 v/v) medium. The complexation of receptor-CN- has been addressed by UV-Vis, fluorescence and 1H NMR spectra and was supported by electrochemical and DFT studies. The mechanism of sensing involves formation of H-bonds between imidazole N-H and CN- ions. The stoichiometry of the receptor-CN- complexes was found to be 1:2 (receptor-CN-) and the detection limit was observed to be in the range of 1.1-3 nM. The test strips based on R5 were fabricated and could act as convenient and efficient CN- test kits. Notably, the novelty of the present investigation is that the receptor R5 selectively senses CN- ions in solid, aqueous and gas phases i.e. 'a complete receptor'.

Solar light active flexible activated carbon cloth-based photocatalyst for Markovnikov-selective radical-radical cross-coupling of S-nucleophiles to terminal alkyne and liquefied petroleum gas sensing

Selective radical-radical coupling of terminal alkynes and thiol has been broadly used in chemical synthesis, providing plausible entries to the formation of anti-Markovnikov products. Because of the selective control and Kharasch effect, the formation of Markovnikov products still remains an immense challenge. Herein, we designed a covalent organic polymer, poly(naphthalene 1,4,5,8-tetracarboxylic dianhydrideimide-benzoquinone) through in situ polymerization on activated flexible carbon cloth to function as a light harvester material for selective Markovnikov radical-radical coupling of terminal alkynes and thiol. Mechanistic explorations verified that cross-coupling between radical of terminal alkynes and thiol might be the key route in this organic transformation, such as C—S bond formation. This selective radical-radical Markovnikov of cross-coupling protocol provide an opportunity to assist the synthesis of valuable vinyl sulfide. Additionally, the synthesized material has been explored as liquefied petroleum gas (LPG) sensor for 0.5, 1.0, 1.5, and 2.0?vol% LPG, respectively. At 2.0?vol% LPG, it shows maximum sensor response as 635.29. Least response and recovery times are 2.44 and 1.0?s, respectively.

Dimensionality Modulates Electrical Conductivity in Compositionally Constant One-, Two-, and Three-Dimensional Frameworks

We reveal here the construction of Ni-based metal-organic frameworks (MOFs) and conjugated coordination polymers (CCPs) with different structural dimensionalities, including closely π-stacked 1D chains (Ni-1D), aggregated 2D layers (Ni-2D), and a 3D framework (Ni-3D), based on 2,3,5,6-tetraamino-1,4-hydroquinone (TAHQ) and its various oxidized forms. These materials have the same metal-ligand composition but exhibit distinct electronic properties caused by different dimensionalities and supramolecular interactions between SBUs, ligands, and structural motifs. The electrical conductivity of these materials spans nearly 8 orders of magnitude, approaching 0.3 S/cm.

In Situ Prepared Solar Light-Driven Flexible Actuated Carbon Cloth-Based Nanorod Photocatalyst for Selective Radical–Radical Coupling to Vinyl Sulfides

A global challenge faced by light harvesting photocatalyst is how to promote the selective organic transformation, such as C-S bond formation via radical–radical coupling under solar light. Here, we report a two-dimensional covalent organic frameworks (2D-COFs), poly (perylene-imide-benzoquinone) nanorod through in?situ condensation on flexible activated carbon cloth (PPIBNR-FACC) to function as a light harvester material for highly selective radical–radical coupling to vinyl sulfides (i.e. C-S bond activation). Such a structure supports charge transfer from PPIBNR to FACC, which is essential for the selective radical–radical coupling. Hence, organic transformation is attaining high yields and selectivity (?99%) under solar light using in?situ prepared PPIBNR-FACC photocatalyst. The structural virtues of PPIBNR-FACC will trigger the utmost investigations into designable and versatile 2D-COFs for fine chemical synthesis.

Reductive Silylation Using a Bis-silylated Diaza-2,5-cyclohexadiene

1,4-Bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadiene, 1, was tested as a reagent for the reductive silylation of various unsaturated functionalities, including N-heterocycles, quinones, and other redox-active moieties in addition to deoxygenation of main group oxides. Whereas most reactions tested are thermodynamically favorable, based on DFT calculations, a few do not occur, perhaps giving limited insight on the mechanism of this very attractive reductive process. Of note, reductive silylation reactions show a strong solvent dependence where a polar solvent facilitates conversions.

Redox-active guanidine ligands with pyridine and p-benzoquinone backbones

Herein we report on the synthesis and some aspects of the chemistry of the new redox-active ligands 2,3,5,6-tetrakis(tetramethylguanidino)pyridine, 2,3,5,6-tetrakis(tetramethylguanidino)-p-benzoquinone and 2,3,5,6-tetrakis(N,N'- dimethyl-N,N'-ethyleneguanidino)-p-benzoquinone. All three ligands are strong electron donors. In addition, the p-benzoquinone systems feature low LUMO energies and small HOMO-LUMO gaps. A comparison of the ligands was made with regard to their optical properties, Bronsted basicity and electron-donor properties; results of quantum chemical calculations were included in this comparison. Subsequently, dinuclear copper complexes were prepared. Preliminary experiments on their redox chemistry followed. Copyright

Electron Transfer and Ion Pairing, 18 ; Radical Anions and Radical Ion Pairs of Aza-Substituted Naphtho- and Anthraquinones

The redox behaviour of aza-substituted naphtho- and anthraquinones, which offer O=C-C=N- chelate tongs for an advantageous five-membered ring metal cation complexation, is investigated by a combination of cyclovoltametric and ESR/ENDOR spectroscopic measurements.The formation of paramagnetic contact ion pairs like .-Me+>., with Me+ = Li+, Na+, Tl+, or of triple ion radical cations like -Me2+>.+ with Me+ = Li+, Na+ is corroborated both by shifts of the second reduction potential of up to 0.67 V for e.g. quinoline 5,8-quinone upon additon of Li+- to its DMF solution and by the observation of ESR/ENDOR metal cuplings.