434-85-5

Usage

Chemical Properties

yellow powder

InChI:InChI=1/C28H16O2/c29-27-21-13-5-1-9-17(21)25(18-10-2-6-14-22(18)27)26-19-11-3-7-15-23(19)28(30)24-16-8-4-12-20(24)26/h1-16H

Upstream product

• 110-86-1 pyridine 
• 434-84-4 bianthronyl 
• 110-46-3 isopentyl nitrite 
• 56-23-5 tetrachloromethane 
• 16014-05-4 9,9'-Bianthracene-10,10'-diol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 75-36-5 acetyl chloride 
• 67-64-1 acetone 
• 106-51-4 p-benzoquinone 
• 602-60-8 9-nitroanthracene 
• 1705-82-4 10-diazo-10H-anthracen-9-one 
• 1068-55-9 isopropylmagnesium chloride 
• 529-86-2 9-anthrol 
• 90-44-8 anthracen-9(10H)-one 

Downstream Products

• 613-31-0 9,10-dihydroanthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 7722-84-1 dihydrogen peroxide 
• 190-39-6 bisanthene 
• 475-64-9 phenanthro[1,10,9,8-opra]prylene-7,14-dione 
• 120207-61-6 10,10'-bis-(4-chloro-phenyl)-10H,10'H-[9,9']bianthrylidene-10,10'-diol 
• 53418-60-3 10,10'-diphenyl-10H,10'H-[9,9']bytrancenylidene-10,10'-diol 
• 1191886-63-1 10,10'-dihydroxy-10,10'-bis(2,4,6-trimethylphenyl)-9,9'-bianthracenylidene 
• 1192537-31-7 C₆₂H₇₆O₄Si₂ 

Relevant academic research and scientific papers

9-Anthracenyl-substitued pyridyl enones revisited: Photoisomerism in ligands and silver(i) complexes

In solution, (E) to (Z)-isomerism is facile both in 3-(9-anthracenyl)-1- (pyridin-4-yl)propenone, 2, and in its silver(i) complex [Ag(2) 2]+. The crystal structures of (E)-2, (Z)-2 and [Ag{(E)-2}2][SbF6] are presented, and the roles of edge-to-face and face-to-face π-interactions in the lattice are discussed. Solution NMR spectroscopic data suggest that the driving force for (E) to (Z) isomerization is intramolecular π-stacking of the pyridine and anthracene domains. The reversed enone 3-(9-anthracenyl)-1-(pyridin-4-yl)propen-3-one, (E)-3, and the silver(i) complex [Ag{(E)-3}2][SbF6] have been prepared and characterized, including a single crystal X-ray determination of the latter. Surprisingly, no π-stacking between anthracene or pyridine domains is observed in the solid state, and the crystal packing is dominated by Ag...F, CHanthracene...π-pyridine and CH...F interactions. In contrast to (E)-2 and [Ag{(E)-2}2]+, neither (E)-3 nor [Ag{(E)-3}2]+ undergoes photoisomerization in solution.

Nature of the Low-Temperature Emission from 9-Nitroanthracene

A luminescence study of 9-nitroanthracene indicates that its emission from EPA glasses at 77 K is not molecular phosphorescence but anthraquinon phosphorescence formed via an efficient photochemical reaction.The quantum yield for the reaction at 77 K in ethyl alcohol is estimated to be 0.7.Evidence that 9-nitroanthracene does not phosphoresce was corroborated by forming 1:1 EDA complex with boron trichloride, which results in a stable complex that inhibits its molecular photodecomposition.

ELECTRON-TRANSFER REACTIONS AND ASSOCIATED CONFORMATIONAL CHANGES. STUDIES OF BIANTHRONE REDUCTION VIA HOMOGENEOUS REDOX CATALYSIS.

The catalyzed reductions of bianthrone (1) and 1,1 prime -dimethylbianthrone have been quantitatively characterized in dimethylformamide solvent. The technique that was employed involves the generation of anion radicals of various quinones at a mercury electrode. As they diffuse near the electrode, these anion radicals can transfer an electron to A form of the bianthrone. At low catalyst concentrations, the rate of reduction of 1 is governed by the forward electron-transfer reaction for each of five quinones. the back reaction was shown to be diffusion controlled. The results were compared with radiolysis studies in a different medium. The present work was the result of interest in the significant role of molecular conformation in the thermodynamics and kinetics of electron-transfer reactions. Refs.

Excited-State Behavior of Thermally Stable Radical Ions

The excited states of several families of thermally stable radical ions in solution are surveyed by transient absorption and steady-state fluorescence spectroscopy to determine prevalent deactivation mode(s).Of the species investigated, weak fluorescence can be observed only for substituted triarylamine radical cations, presumably from their lowest excited doublet states.The primary excited-state deactivation pathway for radical anions of the quinones, aryl ketones, and cyanoarene hydrocarbons examined here is internal conversion from the lowest excited doublet state to the ground-state doublet.The efficiency of this deactivation mode arises typically from a low D0-D1 energy gap, as demonstrated by near-infrared absorbance in each species.Contrary to a prior literature report, the 9,10-anthraquinone radical anion and the 9,10-dicyanoanthracene radical anion are nonluminescent in solution.Luminescent side products generated in ground-state reactions of these radical anions are identified as 9,9-bianthrone dianion (from the dimerization and deoxygenation of the anthraquinone radical anion) and 10-cyanoanthrolate (from the reaction of dicyanoanthracene radical anion with molecular oxygen).

Electron-Transfer Reactions and Conformational Changes Associated with the Reduction of Bianthrone

The electrochemical reduction of the low-temperature A form of bianthrone (1A) at a platinum cathod in DMF proceeds in a two-electron, irreversible reaction, giving the dianion 3B which is structurally similar to the high-temperature B form of bianthrone (1B), having two planar ring system twisted about the central connecting bond.The overall reduction involves a large structural change.By contrast, 3B is rapidly and reversibly oxidized to a structurally similar anion radical, 2B, and then to 1B which is not stable at room temperature and converts to 1A as it diffuses away from the electrode.This scheme was confirmed by cyclic voltammetry and transmission-mode spectroelectrochemistry.Rate constants for both the 1A->1B and 1B->1A reactions were determined, and upper limits were put on the rate constants for the direct electrochemical reduction of 1A to 2B or 3B.

Synthesis and electro-optical evaluation of 2,6-bis(arylethynyl)anthraxquinones

A series of 2,6-bis(arylethynyl)anthraquinones was prepared via double Sonogashira coupling to 2,6-diiodoanthraquinone, and characterized with regard to their optical and electronic properties. Substitution with a derivatized phenylethynyl group produced a λonset of 366 nm (Eg = 3.4 eV), but the more highly conjugated 2,6-bis(9'-anthracylethynyl)anthraquinones exhibited a λonset of approximately 540 nm (Eg = 2.3 eV). Poor solubility in the unsubstituted 9'-anthracylethynyl system hampered complete characterization or purification, but the 10'-hexanoylanthrac-9'-ylethynyl analog exhibited significantly better solubility. The preparation of several other functionalized derivatives was also explored, and key synthetic findings are reported.

Facile synthesis and lateral πnsion of bisanthenes

The improved Scholl reaction allows for the direct cyclization of anthracene oligomers to give bisanthene, teranthene, and quateranthene. Furthermore, a variety of πnded bisanthenes are obtained by the Diels-Alder cyclo-addition of bisanthene with several arynes. These reactions would allow us to synthesize various size- and shape-controlled polyperiacenes.

METHOD OF PRODUCING DIOL, POLYDIOL, SECONDARY ALCOHOL OR DIKETONE COMPOUND

The invention is a process of using, as a reducing agent, a 12CaO·7Al2O3 electride containing electrons in a number of 1019 cm-3 or more and 2.3 × 1021 cm-3 or less in its cages to subject a carbonyl compound to reductive coupling in a solvent, thereby synthesizing a diol or polydiol. The invention is also a process of reducing a ketone compound in a solvent, thereby synthesizing a secondary alcohol or diketone compound. According to the process of the invention, it is possible to synthesize a diol or polydiol, or a secondary alcohol or diketone compound through simple operations in a short period without using an expensive and harmful metal hydride or metal salt nor limiting the atmosphere for the synthesis to an inert gas atmosphere as in conventional processes.

An easy synthesis of thermochromic ethylenes under microwave irradiation

Thermochromic ethylenes were obtained by the reaction of anthrone with tricyclic ketones or terephthaldehyde in DMF in the presence of potassium ter-butoxide under reflux (8h) or under microwave irradiation (10 min.).

Spectral-luminescent properties and photoinduced transformations of bisanthene and bisanthenequinone

Based on the study of photochemical transformations of bisanthene in oxygen-containing solutions, it was established that the final product of this reaction is bisanthenequnone. It is shown that in the course of this oxidation reaction the intermediate compounds endomonoperoxide and bisanthene endobiperoxide are formed. Quantum-chemical calculation of the geometrical structure and electronic spectra of the endoperoxides has shown that they have a nonplanar structure, and their absorption spectra experience a large hypsochromic shift. The absorption and fluorescence spectra of solutions of bisanthene in different solvents at 300 and 77 K were investigated. The large Stokes shift of the fluorescence spectra of the solutions of bisanthene in benzene and in its methyl derivatives is explained by the action of intermolecular interactions. The quasi-line fluorescence spectra of solutions of bisanthene in the matrices of saturated hydrocarbons were recorded.