1055-23-8

Usage

Physical Form

Solid

Uses

9,9'-Bianthracene is a useful research chemical.

Upstream product

• 1564-64-3 9-Bromoanthracene 
• 120-12-7 anthracene 
• 434-84-4 bianthronyl 
• 102185-43-3 10-benzhydryl-anthrone 
• 4393-30-0 10,10′-tetrahydro-9,9′-dihydroxybianthryl 
• 84-65-1 9,10-phenanthrenequinone 
• 100-75-4 N-nitrosopiperidine 
• 64-17-5 ethanol 
• 603-34-9 N,N-diphenylaminobenzene 
• 110-82-7 cyclohexane 
• 90-44-8 anthracen-9(10H)-one 
• 86-74-8 9H-carbazole 
• 98-95-3 nitrobenzene 
• 931-88-4 cis-Cyclooctene 

Downstream Products

• 613-31-0 9,10-dihydroanthracene 
• 103149-25-3 [9,9']Bianthracenyl; compound with benzene 
• 122447-72-7 10-bromo-9,9′-bianthryl 
• 121848-75-7 10,10'-dibromo-9,9'-bianthryl 
• 1505455-95-7 10,10'-bis(2-fluorophenyl)-9,9'-bianthracene 
• 1505455-96-8 10,10'-bis(3-fluorophenyl)-9,9'-bianthracene 
• 1505455-97-9 10,10'-bis(4-fluorophenyl)-9,9'-bianthracene 
• 1505455-98-0 10,10'-bis(2,4-difluorophenyl)-9,9'-bianthracene 
• 1505455-99-1 10,10'-bis(3,4,5-trifluorophenyl)-9,9'-bianthracene 
• 120-12-7 anthracene 

Relevant academic research and scientific papers

Oxidation-state-dependent photochemistry of sulfur-bridged anthracenes

What's up sulfur? The photochemical reactivity, including a mechanistic study of sulfur-bridged anthracenes is reported. The oxidation state of the bridging sulfur (SOn) dictates the excited-state behavior of these molecules (see picture). Copyright

Reversible mechanochromic luminescence of phenothiazine-based 10,10′-bianthracene derivatives with different lengths of alkyl chains

A series of 10,10′-bis(2-(N-alkylphenothiazine-3-yl)vinyl)-9,9′-bianthracene compounds (PVBAn, n = 2, 8, 12 and 16) with different lengths of N-alkyl chains have been designed and synthesized to systematically investigate the effect of chain length on their solid-state fluorescence properties. The results showed that these compounds emitted strong fluorescence in solution and in the solid state. Their emission wavelengths were also strongly affected by solvent polarity, indicating intramolecular charge transfer (ICT) transitions. Interestingly, the fluorescence emission and grinding-induced spectral shifts of PVBAn solids are alkyl length-dependent. PVBA2 shows the smallest fluorescence and absorption spectrum shifts under mechanical force stimuli. Homologues with longer alkyl chains exhibit similar mechanochromic behaviors and larger fluorescence contrasts after grinding. Moreover, the fluorescence emission of ground solid PVBA16 can recover at room temperature, but other compounds need high temperatures for fluorescence to be restored. Differential scanning calorimetry experiments reveal that the cold-crystallization temperature difference is responsible for thermal restoration behaviors. This work demonstrates the feasibility of tuning the solid-state optical properties of fluorescent organic compounds by combining the simple alteration of chemical structure and the physical change of aggregate morphology under external stimuli.

Fine tuning of bipolar side group on dual anthracene core derivatives for highly efficient blue emitters

Three bipolar blue fluorescent materials were newly synthesized by attaching diphenylamine (DPA), triphenylamine (TPA), and 9-phenylcarbazole amine (PCA) as an electron donating group and 2,4- diphenyl-1,3,5-triazine (DPT) as an electron withdrawing group to the dual anthracene core moiety. Compounds are [10'-(4,6-Diphenyl-[1,3,5]triazin-2-yl)-[9,9']bianthracenyl-10-yl]-diphenyl-amine (DPA-AA-DPT), {4-[10'-(4,6-Diphenyl-[1,3,5]triazin-2-yl)-[9,9']bianthracenyl-10-yl]-phenyl}-diphenyl- amine (TPA-AA-DPT), and 9-(4-(10'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[9,9′-bianthracen]-10-yl)phenyl)- 9H-carbazole (PCA-AA-DPT), respectively. The optical, thermal, and electroluminescence (EL) properties of the synthesized materials were measured. Newly bipolar materials were found to have blue emission in the solution state and to acquire high PLQY values. A device doped with PCA-AA- DPT showed a very high efficiency of 6.86 cd/A and EQE of 5.53% at a high current density without roll-off phenomenon.

EXPERIMENTAL STUDY OF DIMERIZATION OF RADICAL ANIONS OF AROMATIC CARBONYL COMPOUNDS

The rate constants of dimerization (k1) of radical anions of acetophenone, 1-acetylnaphthalene, 9-acetylanthracene, 9-formylanthracene, and anthracene in DMF containing 0.02 M tetrabutyloammonium bromide were determined by differential cyclic voltammetry.It was shown that the values of k1 of the radical anions investigated are correlated with the values of the boundary electron density on the reaction sites, which in turn increase symbatically with an increase in the size of the aryl fragment or on incorporation of electron-acceptor functional groups in the anthracene nucleus.

A laser desorption ionization mass spectrometry investigation of triarylboranes and tri-9-anthrylborane photolysis products

Laser desorption ionization (LDI) mass spectra have been obtained for the photolysis products of tri-9-anthrylborane (TAB) in the solvents toluene, cyclohexene, and tetrahydrofuran; and for the solid triarylboranes: TAB, trimesitylborane (TMB), and tri-(2,6-dimethylphenyl)borane (TXyB). The major single solution photolysis product of TAB is 9,9′-dianthryl. Other products are rationalized in terms of an anthrylborylene intermediate (AnthB:). LDI mass spectrometry of the triarylboranes yields molecular ions in good abundance, providing a simple and selective method of characterization. Fragmentation patterns in some cases are interpreted in terms of photochemical reactions prior to ionization.

Photochemical reaction of anthracene in cyclohexane polycrystals dispersed in liquid nitrogen

U.v. photolysis of a polycrystalline solution of anthracene in cyclohexane at 77 K followed by separation of the stable photoproducts at room temperature, yielded 9,10-dihydroanthracene, 9-cyclohexyl-9,10-dihydroanthracene, 9-cyclohexylanthracene, and oxidized derivatives of anthracene.

Diphenylanthracene Dimers for Triplet-Triplet Annihilation Photon Upconversion: Mechanistic Insights for Intramolecular Pathways and the Importance of Molecular Geometry

Novel approaches to modify the spectral output of the sun have seen a surge in interest recently, with triplet-triplet annihilation driven photon upconversion (TTA-UC) gaining widespread recognition due to its ability to function under low-intensity, noncoherent light. Herein, four diphenylanthracene (DPA) dimers are investigated to explore how the structure of these dimers affects upconversion efficiency. Also, the mechanism responsible for intramolecular upconversion is elucidated. In particular, two models are compared using steady-state and time-resolved simulations of the TTA-UC emission intensities and kinetics. All dimers perform TTA-UC efficiently in the presence of the sensitizer platinum octaethylporphyrin. The meta-coupled dimer 1,3-DPA2 performs best yielding a 21.2% upconversion quantum yield (out of a 50% maximum), which is close to that of the reference monomer DPA (24.0%). Its superior performance compared to the other dimers is primarily ascribed to the longer triplet lifetime of this dimer (4.7 ms), thus reinforcing the importance of this parameter. Comparisons between simulations and experiments reveal that the double-sensitization mechanism is part of the mechanism of intramolecular upconversion and that this additional pathway could be of great significance under specific conditions. The results from this study can thus act as a guide not only in terms of annihilator design but also for the design of future solid-state systems where intramolecular exciton migration is anticipated to play a major role.

Facile and fast pinacol rearrangement by AlCl3 in the solid state

A facile and efficient synthetic procedure for effecting the pinacol rearrangement catalyzed by AlCl3 in the absence of solvent is developed. The rearrangement product is obtained at room temperature in a few minutes and in almost quantitative yield. Benzylic pinacols rearrange under these conditions, while aliphatic pinacols do not react.

Effect of molecular conformation on the efficiency of the spin orbital charge recombination-induced intersystem crossing in bianthryls

Two bianthryl dyads, with the two units connected at either the 2- or 9- positions of the anthryl moiety, were studied to establish the relationship between orientation of the anthryl moieties and the electronic coupling and intersystem crossing (ISC) efficiency. The anthryl moieties in the two dyads adopt a close-to-orthogonal geometry, with dihedral angles of 90° (9,9′-bianthryl) and 106° (2,9′-bianthryl) at the ground state, respectively. The charge transfer (CT) emission efficiency and the fluorescence lifetimes are clearly dependent on the electronic coupling between the two anthryls, and stronger coupling lead to higher fluorescence quantum yields (34% vs. 9%) and shorter luminescence lifetimes (13.9 ns vs. 38.6 ns). The bianthryl with more orthogonal geometry shows higher singlet oxygen quantum yields ΦΔ (9,9′-bianthryl, ΦΔ = 53%) than 2,9′-bianthryl (ΦΔ = 32%). Moreover, highly solvent polarity-dependent fluorescence emission and ΦΔ were observed for the dyads (ΦΔ = 22–53%), which is different from the trend of the monomer anthracene, thus we propose the spin-orbit charge transfer ISC (SOCT-ISC) is responsible for the triplet state productions of the dyads. Interestingly, we found that inducing a heavy atom (Br) does not increase the ISC yield of anthracene. ISC in bianthryls was also confirmed with nanosecond transient absorption spectroscopy, the featured T1→Tn absorption at ca. 433 nm was observed, and the triplet state lifetime are long (9,9′-bianthryl, τT = 353 μs; 2,9′-bianthryl, τT = 493 μs, in acetonitrile).

Photoluminescence, redox properties, and electrogenerated chemiluminescence of twisted 9,9′-bianthryls

To study the dual emission (from locally excited and charge transfer states) of sterically crowded 9,9′-bianthryl (BAHO) and its 10,10′-disubstituted derivatives, namely, 10,10′-dibromo-9,9′- bianthryl (BABR), 10,10′-bis(p-tolylethynyl)-9,9′-bianthryl (BAET), and 10,10′-bis(N,N-diphenyl-4-anilino)-9,9′-bianthryl (BATA) in detail, we probed their photophysical, redox, and electrogenerated chemiluminescence (ECL) responses. Dual emission for all of the molecules was noticed in PL, whereas in ECL only charge transfer emission was observed over a variety of experimental conditions. The PL in nonpolar solvents is significantly influenced by added supporting electrolyte, yielding exclusively charge transfer emission as in ECL. The stability of ECL proved to depend largely on the nature of the substituent, with triarylamine and bromo groups imparting constant ECL intensity over more than 60 cycles.