129-42-0

Usage

Uses

Used in Dye Industry:
1,8-diaminoanthraquinone is used as a dye intermediate for the production of various dyes, particularly vat dyes, which are essential for coloring textiles, paper, and plastics.
Used in Chemical Research:
1,8-diaminoanthraquinone serves as a building block for the synthesis of other organic molecules, contributing to the advancement of chemical research and development.

InChI:InChI=1/C14H10N2O2/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6H,15-16H2

Upstream product

• 136918-14-4 phthalimide 
• 82-43-9 1,8-dichloroanthraquinone 
• 33522-40-6 1,8-bis-(toluene-4-sulfonylamino)-anthraquinone 
• 129-39-5 1,8-dinitroanthraquinone 
• 209176-56-7 C₃₀H₁₄N₂O₆ 

Downstream Products

• 82-43-9 1,8-dichloroanthraquinone 
• 83578-92-1 1,8-diamino-2,4,5,7-tetrachloro-anthraquinone 
• 63216-87-5 N,N'-(9,10-dioxo-9,10-dihydro-anthracene-1,8-diyl)-bis-oxalamic acid 
• 10114-51-9 1,8-Bis-benzamidoanthrachinon 
• 82-45-1 1-amino-9,10-anthracenedione 
• 1064704-71-7 C₇₀H₆₄N₈O₁₀ 
• 82-36-0 1,8-bis-acetylamino-anthraquinone 
• 1351191-73-5 benzo[1,2-h:5,4-h']di(4-phenylquinoline) 

Relevant academic research and scientific papers

Unique hydrogen bonds between 9-anthracenyl hydrogen and anions

Unique hydrogen bonds of the 9-H of anthracene moieties in hosts 1 and 2 with fluoride and pyrophosphate ions were observed on the basis of the 1H NMR experiments. Furthermore, hosts 1 and 2 act as a colorimetric sensor and a fluorescent chemosensor for the recognition of fluoride ion, respectively.

Human telomerase inhibition by regioisomeric disubstituted amidoanthracene-9,10-diones

Telomerase is an attractive target for the design of new anticancer drugs. We have previously described a series of 1,4- and 2,6-difunctionalized amidoanthracene-9,10-diones that inhibit human telomerase via stabilization of telomeric G-quadruplex structures. The present study details the preparation of three further, distinct series of regioisomeric difunctionalized amidoanthracene-9,10-diones substituted at the 1,5-, 1,8-, and 2,7-positions, respectively. Their in vitro cytotoxicity and Taq DNA polymerase and human telomerase inhibition properties are reported and compared with those of their 1,4- and 2,6-isomers. Potent telomerase inhibition ((tel)IC50 values 1.3-17.3 μM) is exhibited within each isomeric series. In addition, biophysical and molecular modeling studies have been conducted to examine binding to the target G-quadruplex structure formed by the folding of telomeric DNA. These studies indicate that the isomeric diamidoanthracene-9,10-diones bind to the human telomeric G-quadruplex structure with a stoichiometry of 1:1. Plausible G-quadruplex-ligand complexes have been identified for each isomeric family, with three distinct modes of intercalative binding being proposed. The exact mode of intercalative binding is dictated by the positional placement of substituent side chains. Furthermore, in contrast to previous studies directed toward triplex DNA, it is evident that stringent control over positional attachment of substituents is not a necessity for effective telomerase inhibition.

Syntheses and structures of hypervalent pentacoordinate carbon and boron compounds bearing an anthracene skeleton - Elucidation of hypervalent interaction based on X-ray analysis and DFT calculation

Pentacoordinate and tetracoordinate carbon and boron compounds (27, 38, 50-52, 56-61) bearing an anthracene skeleton with two oxygen or nitrogen atoms at the 1,8-positions were synthesized by the use of four newly synthesized tridentate ligand precursors. Several carbon and boron compounds were characterized by X-ray crystallographic analysis, showing that compounds 27, 56-59 bearing an oxygen-donating anthracene skeleton had a trigonal bipyramidal (TBP) pentacoordinate structure with relatively long apical distances (ca. 2.38-2.46 A). Despite the relatively long apical distances, DFT calculation of carbon species 27 and boron species 56 and experimental accurate X-ray electron density distribution analysis of 56 supported the existence of the apical hypervalent bond even though the nature of the hypervalent interaction between the central carbon (or boron) and the donating oxygen atom was relatively weak and ionic. On the other hand, X-ray analysis of compounds 50-52 bearing a nitrogen-donating anthracene skeleton showed unsymmetrical tetracoordinate carbon or boron atom with coordination by only one of the two nitrogen-donating groups. It is interesting to note that, with an oxygen-donating skeleton, the compound 61 having two chlorine atoms on the central boron atom showed a tetracoordinate structure, although the corresponding compound 60 with two fluorine atoms showed a pentacoordinate structure. The B-O distances (av 2.29 A) in 60 were relatively short in comparison with those (av 2.44 A) in 59 having two methoxy groups on the central boron atom, indicating that the B-O interaction became stronger due to the electron-withdrawing nature of the fluorine atoms.

Designed synthesis of ferrocenylanthraquinones and their bifunctional electrochromic properties

(Figure Presented) New bifunctional electrochromic systems were developed by combination of reductive anthraquinone with oxidative ferrocene redox systems. The resultant ferrocenylanthraquinones demonstrated enhanced stability in electrochromic performanc

Three anthracene-based bis-imidazolium salts: Synthesis, structure and recognition for 2,4-dinitrophenylhydrazine

Three anthracene-based bis-imidazolium salts 1,8-bis [2’-(N-R-imidazoliumyl) acetamido]anthracene 2× (1: R = nBu, X = Cl?; 2: R = nBu, X = PF6 ?; 3: R = Et, X = PF6 ?) were prepared. The structure of 1 was demonstrated by X-ray analysis. The selective recognition of 2 (or 3) for some aromatic compounds (toluene, chlorobenzene, phenylamine, phenol, anisole, benzaldehyde, acetophenone, nitrobenzene, m-dinitrobenzene, 2,4-dinitrotoluene, 2,4-dinitrophenylhydrazine (DNP), trinitrophenol, o-nitrophenol, p-nitrotoluene) was investigated through fluorescence, ultraviolet, 1H NMR, HRMS and IR spectra at 25 °C. Compounds 2 (or 3) showed good selective recognition ability for DNP, and they could effectively distinguish DNP from other aromatic compounds. The association constants and detection limits of 2 and 3 were similar, which displayed sizes of side chains (nBu for 2 and Et for 3) had no remarkable effect on the recognition of DNP.

Anthracene Bisureas as Powerful and Accessible Anion Carriers

Synthetic anion carriers (anionophores) have potential as biomedical research tools and as treatments for conditions arising from defective natural transport systems (notably cystic fibrosis). Highly active anionophores that are readily accessible and eas

Organic cage inclusion crystals exhibiting guest-enhanced multiphoton harvesting

Host-guest complexation is an important supramolecular route to materials. Clear design rules have been developed for complexation in solution. This has proved more challenging for solid-state host-guest co-crystals because they often exhibit polymorphism, leading many researchers to focus instead on bonded frameworks, such as metal-organic frameworks. Here, we report an anthracene-based organic cage (1) that forms isoskeletal host-guest co-crystals with five similarly sized solid organic guests. The co-crystals were designed using inexpensive computational methods to identify appropriate guests that have packing coefficients (PCs) ranging from 44% to 50%, coupled with consideration of the guest shape. By complexing highly emissive BODIPY guests into the host structure, we enhanced its two-photon excited photoluminescent properties by a factor of six. Our crystal design approach was also transferrable to hard-to-design ternary organic crystals that were accessed by inserting specific guests into different sized voids in the host.

Synthesis, structures and luminescence properties of N^C^N-coordinated platinum(II) complexes based on an anthracene core: A red shift and a twist

1,8-Bis(2-pyridyl)anthracene HL2 is shown to act as a tridentate, N^C^N-coordinating ligand to platinum(II), undergoing metallation at position 9 of the anthracene. The structures of Pt(N^C^N-L2)Cl and of HL2 have been determined by X-ray diffraction. The complex features two 6-membered chelate rings and an N-Pt-N bite angle of 178.16(7)°, close to the “ideal” value of 180°. The attainment of this angle necessitates not only a twisting of the pyridyl rings relative to the anthracene, but also a remarkable twisting distortion of the anthracene unit itself. The complex is isomeric with the previously reported Pt(d8qb)Cl {d8qb = 1,3-di(8-quinolyl)benzene}. A new derivative of the latter has been prepared, PtL3Cl, featuring methyl substituents in the central benzene ring ortho to the quinolines. Like PtL2Cl, its structure shows twisting of the coordinated heterocycles relative to the plane of the central aromatic ring. The Pt(II) complex PtL1Cl of a related N^C^N-coordinating ligand featuring extended conjugation, benzo[1,2-h: 5,4 = h’]diquinoline HL1, has also been prepared following a previously described procedure. PtL1Cl is brightly phosphorescent in deoxygenated solution at ambient temperature, in the red region of the spectrum. The impressive photoluminescence quantum yield of 0.30 and long emission lifetime of 38 μs are indicative of a rigid structure with little excited state distortion. In contrast, PtL2Cl shows no detectable emission, probably due to the distorted nature of the structure leading to rapid non-radiative decay of the excited state. This result contrasts with the weak red emission displayed by the isomeric Pt(d8qb)Cl and its dimethylated derivative PtL3Cl.

Anthrabiimidazole salt compound and preparation method and application thereof

The invention discloses a preparation method and use of an anthrabiimidazole salt compound. The preparation method comprises that 1, 8-dinitroanthraquinone as a raw material, sodium sulfide and sodiumhydroxide undergo a reaction in an organic solvent to produce 1, 8-diaminoanthraquinone, the reaction product, sodium borohydride and sodium hydroxide undergo a reaction to produce 1, 8-diaminomethylanthracene, the 1, 8-aminomethylanthracene, chloroacetyl chloride and triethylamine undergo a reaction to produce 1, 8-dichloroacetamidoanthracene, the 1, 8-dichloroacetamidoanthracene and 1-n-butylimidazole undergo a reaction under reflux to produce 1, 8-bis[1-n-butyl-imidazolylacetamido]anthracene chloride (1), and the 1, 8-bis[1-n-butyl-imidazolylacetamido]anthracene chloride and NH4PF6 are subjected to anion exchange so that 1, 8-bis[1-n-butyl-imidazolylacetamido]anthracene hexafluorophosphate (2) is obtained. The anthrabiimidazole salt compound is prepared through simple processes, has obvious fluorescence sensitization effects, is sensitive to some specific objects, can be used for preparation of a fluorescent molecular recognition system and is mainly used in the technical field offluorescent probes.

POLYMERIZABLE DICHROIC DYES

The present invention relates to new dichroic dyes, their composition with slave materials and their use for a dichroic polymer network, a dichroic liquid crystalline polymer film (LCP film) or a dichroic liquid crystalline polymer gel, which for instance find application as electro- optical or optical devices.