122447-72-7

Basic information

• Product Name: 10-bromo-9,9'-bianthracene
• Synonyms: 10-bromo-9,9'-bianthracene
• CAS NO: 122447-72-7
• Molecular Formula: C₂₈H₁₇Br
• Molecular Weight: 433.33858
• Mol File: 122447-72-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 10-bromo-9,9'-bianthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 10-bromo-9,9'-bianthracene(122447-72-7)
• EPA Substance Registry System: 10-bromo-9,9'-bianthracene(122447-72-7)

Safety Data

• Hazardous Substances Data: 122447-72-7(Hazardous Substances Data)

Usage

Type of compound

Chemical compound

Derivative of

Bianthracene (a polycyclic aromatic hydrocarbon and a derivative of anthracene)

Physical state

Yellow crystalline solid

Usage

Organic synthesis (building block for various organic compounds)

Application field

Material science (development of organic semiconductor materials)

Bromo group

Makes it versatile for further chemical reactions

Potential applications

Development of new materials for electronics and optoelectronics

Importance

Significant chemical compound with potential uses in scientific and industrial applications

Upstream product

• 84-65-1 9,10-phenanthrenequinone 
• 187-98-4 Tetradehydrodianthracene 
• 1055-23-8 9,9'-bianthracene 
• 1564-64-3 9-Bromoanthracene 

Relevant articles and documents

On-Surface Synthesis and Characterization of Triply Fused Porphyrin–Graphene Nanoribbon Hybrids

On-surface synthesis offers a versatile approach to prepare novel carbon-based nanostructures that cannot be obtained by conventional solution chemistry. Graphene nanoribbons (GNRs) have potential for a variety of applications. A key issue for their appli

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.

Highly efficient dual anthracene core derivatives through optimizing side groups for blue emission

TP-AA-TPB, TP-AA-TPB, TPB-AA-TPB, TP-AA-DPA, TP-AA-TPA, and TPB-AA-TPA were synthesized using a 9,9'-bianthracene (AA core). Through a systematic side group change, we optimized the dual-core chromophore system and investigated the relationship between the core and the side groups. The ultraviolet-visible (UV-Vis) absorption of the six materials showed an intrinsic absorption peaks of anthracene in the range of 360 nm–410 nm and photoluminescence (PL) emission in the blue region. The minimum decomposition temperatures (Td) was 425 °C, the minimum melting temperatures (Tm) was 335 °C, and the minimum glass transition temperatures (Tg) was 176 °C. We achieved excellent overall electroluminescence (EL) efficiency in non-doped OLED devices using the six synthesized materials as emitting layer (EML). TPB-AA-TPA synthesized through size and polarity optimization of the side groups on the AA core had a current efficiency of 8.97 cd/A, power efficiency of 4.43 lm/W, external quantum efficiency (EQE) of 6.37%, and Commission Internationale de L'Eclairage coordinates (CIE) of (0.14, 0.19). TPB-AA-TPA also maintained blue emission and realized the highest EL efficiency among the six synthesized materials.

INDENOTRIPHENYLENE DERIVATIVES AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME

The present invention discloses a new indenotriphenylene derivatives and organic light emitting device using the derivatives. The organic light emitting device employing new indenotriphenylene derivatives as host material can lower driving voltage, prolong half-lifetime, increasing efficiency. The new indenotriphenylene derivatives are represented by the following formula (A): Wherein A1, A2 are substituted or unsubstituted fused ring hydrocarbon units with one to five rings. Preferably A1, A2 are phenyl group, naphthyl group, anthracenyl group, pyrenyl group, chrysenyl group. Perylenyl group. R1 to R4 are identical or different. R1 to R4 are independently selected from the group consisting of a hydrogen atom, a halide, alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms. X is selected from carbon atom or nitrogen atom.

Photoinduced C-C reactions on insulators toward photolithography of graphene nanoarchitectures

On-surface chemistry for atomically precise sp2 macromolecules requires top-down lithographic methods on insulating surfaces in order to pattern the long-range complex architectures needed by the semiconductor industry. Here, we fabricate sp2-carbon nanometer-thin films on insulators and under ultrahigh vacuum (UHV) conditions from photocoupled brominated precursors. We reveal that covalent coupling is initiated by C-Br bond cleavage through photon energies exceeding 4.4 eV, as monitored by laser desorption ionization (LDI) mass spectrometry (MS) and X-ray photoelectron spectroscopy (XPS). Density functional theory (DFT) gives insight into the mechanisms of C-Br scission and C-C coupling processes. Further, unreacted material can be sublimed and the coupled sp2-carbon precursors can be graphitized by e-beam treatment at 500 °C, demonstrating promising applications in photolithography of graphene nanoarchitectures. Our results present UV-induced reactions on insulators for the formation of all sp 2-carbon architectures, thereby converging top-down lithography and bottom-up on-surface chemistry into technology.

Electrophilic Additions to Tetradehydrodianthracene

5,12:6,11-Dibenzenodibenzocyclooctene (tetradehydrodianthracene, TDDA) (1) reacts with halogens to give transannular (anti) 4, 5 and ring-opened (syn) products 6, 7.The product ratio shows a remarkable solvent dependence.Solvents of medium polarity favor anti addition, whereas syn addition is observed both with increasing and decreasing polarity.For instance, chlorine in toluene adds 100percent syn, in dichloroethane 56percent anti, and in trifluoroethanol again 100percent syn.It is concluded that, depending on solvent polarity, three different mechanisms for electrophilic addition are operative. - Keywords: Electrophilic addition / Tetradehydrodianthracene / Solvent effects

Novel oligo(9,10-anthrylene)s: Models for electron transfer and high-spin formation

Newly synthesized soluble oligo(9,10-anthrylene)s 1 have been subjected to reduction with alkali metal. The electron paramagnetic resonance/electron nuclear double resonance (EPR/ENDOR) studies of corresponding dimer, trimer, and tetramer monoradicals demonstrate that the rate of intramolecular electron transfer between anthracene moieties sensitively depends on the special substitution pattern and the ion pair structure. These features allow for a switching from effectively delocalized to localized states. In agreement with theoretical investigations, high-spin formation of the higher charged species has been obtained. The maximum spin multiplicity received so far is a quintet state for the tetraanion of the tetraanthrylene. The stability of the highly charged states is proven by NMR spectroscopic investigations, where a completely reduced diamagnetic hexaanion of trianthrylene has been characterized by 1H and 13C NMR. As revealed by temperature dependent EPR measurement of the dimer dianion, the triplet state is thermally excited (signal intensity reaches a maximum at 20 K) and the zero-field splitting loses its axial character (typical for orthogonal alignment) at low temperatures, pointing to increased orthorhombicity with decreasing temperature (100-10 K). Although the ground state is singlet, the energy of the triplet state lies only 60 cal/mol above that of the singlet. Surprisingly also the higher spin states of the oligomers were found to be thermally activated with 120 cal/mol for the doublet-quartet (S = 3/2) transition and 180 cal/mol for the quintet-singlet (S = 2) transition.

Photochemical Reactions of Bromoanthracenes with N,N-Dimethylaniline in Solution

Major products of the photolysis of 9-bromoanthracene and 9,10-dibromoanthracene in benzene and acetonitrile as well as photochemical reaction products of the two bromoanthracenes with N,N-dimethylaniline in these solvents have been isolated and identified.The mechanisms of partial reactions are discussed and attention is paid to the medium effect on the photochemical transformations. - Keywords: Photochemical Reactions, Bromoanthracenes