49610-35-7

Usage

Uses

Used in Pharmaceutical Industry:
4,4'-Dibromo-1,1'-binaphthyl is used as a chiral ligand for the development of enantioselective catalysts, which are crucial in the synthesis of chiral drugs. The application reason lies in its capacity to selectively interact with specific molecules, facilitating the creation of pharmaceutical compounds with desired chiral properties, thereby enhancing the efficacy and reducing side effects of drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4,4'-Dibromo-1,1'-binaphthyl is utilized as a chiral building block for the construction of complex organic molecules with specific stereochemistry. Its unique structure allows for the precise control of molecular asymmetry, which is essential in the synthesis of biologically active compounds and advanced materials.
Used in Asymmetric Catalysis:
4,4'-Dibromo-1,1'-binaphthyl is employed as a chiral ligand in asymmetric catalysis, where it plays a pivotal role in inducing asymmetry in chemical reactions. This application is vital for the production of enantiomerically pure compounds, which are often required in various industries, including pharmaceuticals, agrochemicals, and fragrances, to ensure the desired biological activity and avoid potential adverse effects.
Used in Research and Development:
In the research and development sector, 4,4'-Dibromo-1,1'-binaphthyl serves as a valuable tool for studying the mechanisms of asymmetric reactions and the development of new catalytic systems. Its unique properties provide insights into the fundamental aspects of chirality and contribute to the advancement of enantioselective synthetic methods.

Upstream product

• 604-53-5 1,1'-bisnaphthalene 
• 73453-34-6 4,4'-Dibromo-1,1'-binaphthyl 
• 90-11-9 1-Bromonaphthalene 

Downstream Products

• 1260404-93-0 4,4'-dimesityl-1,1'-binaphthyl 
• 1260404-97-4 4,4?-dimesityl-1,1′:4′,1″:4″,1?-quaternaphthalene 
• 1448855-11-5 4,4?-bis(2,3,4,5,6-pentamethylphenyl)-1,1′:4′,1″:4″,1?-quaternaphthalene 
• 1062555-23-0 C₆₉H₄₆ 
• 1062555-69-4 C₅₄H₃₃Br 
• 1062555-68-3 C₅₄H₃₄ 
• 1217293-78-1 4,4'-bis(3,3,3-tri(phenyl-d5)propynyl)-1,1'-binaphthyl 
• 143076-97-5 3,10-diphenylperylene 
• 74866-23-2 4,4'-diphenyl-1,1'-binaphthalene 
• 1374559-53-1 4'-bromo-N,N-diphenyl-1,1'-binaphthyl-4-amine 
• 1374559-41-7 C₄₀H₂₆N₂O₂S 
• 1374559-57-5 5-(4'-(diphenylamino)-1,1'-binaphthyl-4-yl)thiophene-2-carbaldehyde 
• 1374559-55-3 N,N-diphenyl-4'-(thiophen-2-yl)-1,1'-binaphthyl-4-amine 

Relevant academic research and scientific papers

Highly efficient blue light-emitting diodes using new fluorescent host materials based on naphthalenes

The naphthalene-based blue materials 4,4′-(Dinaphthalen-2-yl)-1, 1′-binaphthyl (DNBN) and 1,4-(Dinaphthalen-2-yl)-naphthalene (DNN) were designed and synthesized for OLEDs. A device (non-doped) employing DNN as the emitter exhibited a maximum luminance, luminous efficiency, and external quantum efficiency of 1120cd/m2, 1.40cd/A, and 3.83%, respectively. Moreover, its CIE coordinates (0.152, 0.069) are very close to the NTSC blue standard of (0.14, 0.08). In order to improve EL efficiencies, these materials were used as the blue host materials for the blue dopants PFVtPh and PCVtPh. A device 1b (PFVtPh-doped) showed high EL efficiencies of 5.24cd/A, 2.75lm/W, and 3.82% at 20mA/cm2. Copyright Taylor & Francis Group, LLC.

Synthesis and electroluminescent properties of blue-light-emitting arylene derivatives end-capped with thiophene groups

In this study, four blue fluorescent arylenes end-capped with thiophene derivatives have been synthesized. To explore electroluminescent properties of these molecules, multilayer OLEDs device structure of ITO/NPB/EML/BPhen/Al were fabricated. Two multilayer devices, using 3-4, showed the efficient deep blue emissions with CIEx,y of (0.159, 0.092) and (0.151,0.082) at 9.0V, and the external quantum efficiencies of 1.60 and 0.80%, respectively. A PFVtPh doped-device exhibited the highly efficient blue emission with a maximum luminance of 3480 cd m2 at 9.0V, the external quantum efficiency of 5.23%, and CIEx,y of (0.151, 0.185) at 9.0V. Copyright

Biphenalenylidene: Isolation and Characterization of the Reactive Intermediate on the Decomposition Pathway of Phenalenyl Radical

First isolation and characterization of biphenalenylidenes, which have long been unidentified reactive intermediates on the decomposition pathway of phenalenyl radical, were accomplished. Photoinduced electrocyclic ring-opening reaction of anti-dihydroperopyrene resulted in a successful conversion to E-biphenalenylidene, which enabled a detailed investigation of the electronic structure of E-biphenalenylidene by means of spectroscopic techniques. A stereoisomer, Z-biphenalenylidene, was also observed by suppressing a facile E-Z isomerization to E-biphenalenylidene in a rigid matrix. Furthermore, Z-biphenalenylidene demonstrated a thermal ring-closure in conrotatory process, which is not conforming to the Woodward-Hoffmann rule. These unusual reactivities of biphenalenylidene are ascribed to the ground states destabilized by its singlet biradical character, which was fully supported by theoretical calculations. The presence of E-biphenalenylidene on the decomposition pathway of phenalenyl was confirmed experimentally, leading to the full understanding of the decomposition mechanism of phenalenyl.

Heterogeneous Catalytic Racemization of 4,4'-Disubstituted 1,1'-Binaphthyls by Active Carbons and by Modified Carbon Catalysts

The racemization of four 4,4'-disubstituted 1,1'-binaphthyls is heterogeneously catalyzed by active carbon or carbon black suspended in chloroform solutions.In the presence of 1 mg/mL of Norit SG1 in chloroform the observed first-order rate constants for racemization of 0.025 M substrate were increased over the uncatalyzed rate constants by factors of 2.9, 6.7, 8.3, 8.1, and 14 for disubstituents NH2, CH3, Br, NO2, and H, respectively.The rates of uncatalyzed racemization of these binaphthyls are electronically influenced by the para substituents (giving a Hammett ρof -0.88) and the catalyzed racemization rates show a similar but slightly decreased substituent effect (ρ = -0.57).However, a small steric effect is indicated for the catalyzed reaction since all substituted compounds are less sensitive to catalysis than is 1,1'-binaphthyl itself.Bromination or chlorination of a carbon black results in increased catalytic activity, and potassium-graphite intercalate is an effective, but irratic, racemization agent.An electron-accepting binaphthyl molecule, loosely bound on electron-donor sites of the graphitic basal planes of carbon catalysts, is suggested as an intermediate complex in the catalyzed racemization.

Facile three-step synthesis and photophysical properties of [8]-, [9]-, and [12]cyclo-1,4-naphthalene nanorings: Via platinum-mediated reductive elimination

Herein we report a facile three-step synthesis of [8]-, [9]-, and [12]cyclo-1,4-naphthalene nanorings as the conjugated segments of carbon nanotubes. The nanorings were created via a platinum-mediated assembly of 1,4-naphthalene-based units and subsequent reductive elimination in the presence of triphenylphosphine. This present platinum-mediated approach is attractive because of its simple three-step process to produce the targeted nanorings in a high overall yield. In addition, their photophysical properties were studied using UV-vis spectroscopy and photoluminescence (PL) spectroscopy, which further revealed their unique size-dependent properties.

Aromatic amine compounds and their applications in organic electroluminescent devices

The present invention relates to an aromatic compound and its application in an organic electroluminescent device, the aromatic amine compound having a structure shown in formula (1): the above-described aromatic amine compound by the introduction of an alkyl or aramidyl cyclostis substituent at the 8 and 8' positions of the binaphthalene group, such that the conjugate plane of the binaphthalene is distorted, reducing the effect of intermolecular stacking, is conducive to improving the electroluminescence efficiency, prolonging the life of the device. At the same time, the above-mentioned aromatic amine organic compounds introduce multiple conjugate systems on the triphenylamine unit, thereby effectively dispersing the influence of nitrogen atoms on the C-H bond on the triphenylamine benzene ring, making its chemical structure more stable and has a better device life, which can be used as a hole transport layer material in organic electroluminescent elements, which can improve electroluminescence efficiency and extend the life of the device.

Access to Functionalized Pyrenes, Peropyrenes, Terropyrenes, and Quarterropyrenes via Reductive Aromatization

Herein we report a versatile concept for the synthesis of fourfold functionalized, soluble pyrenes, peropyrenes, terropyrenes, and quarterropyrenes. They were obtained by a modular stepwise approach towards the rylene scaffold via Suzuki–Miyaura cross coupling, oxidative cyclodehydrogenation in the presence of caesium hydroxide under air, and finally zinc-mediated reductive silylation. The silylated reaction products were characterized by X-ray crystallography. The first example of a synthesized and crystallized quarterropyrene is presented and its oxidation reaction investigated. The functionalized ropyrenes were systematically characterized by means of UV/Vis–NIR and photoluminescence spectroscopy showing a bathochromic shift of 80 nm per naphthalene unit and a nearly linear increase of the extinction coefficients. Cyclic voltammograms and DFT calculations identify them as electron-rich dyes and show a narrowing of the electrochemically determined HOMO–LUMO gap and lower oxidation potentials for the higher homologues.

Copper-catalyzed arylation of polycyclic aromatic hydrocarbons by the PO group

The first example of a directed and regioselective arylation of polycyclic aromatic hydrocarbons (PAHs) by using a PO directing group is reported herein. The protocol uses a cheap copper catalyst, and results in a breakthrough meta-selective C-H functionalization of arylphosphine oxide compounds. Substrates with potential fluorescence properties, for example, pyrene and fluoranthene, were successfully arylated under the system, thus achieving an efficient modification of fluorescent molecules containing the PO functional group. This journal is

Tailoring the pore geometry and chemistry in microporous metal-organic frameworks for high methane storage working capacity

We realized that tailoring the pore size/geometry and chemistry, by virtue of alkynyl or naphthalene replacing phenyl within a series of isomorphic MOFs, can optimize methane storage working capacities, affording an exceptionally high working capacity of

Reconnaissance of reactivity of an Ag(II)SO4 one-electron oxidizer towards naphthalene derivatives

We test divalent silver sulphate, Ag(ii)SO4 as a novel reagent for oxidative coupling of aromatic hydrocarbons under ambient temperature conditions. The applicability of the C(sp2)-C(sp2) coupling protocol is illustrated for naphthalene and its 1-substituted derivatives containing either electron donating (e.g. Me, MeO, or Ph) or electron-withdrawing groups (X = F?I), leading to 4,4′-disubstituted-1,1′-binaphthyls. Coupling of 2-bromo-naphthalene yields a mixture of 2,2′-, 2,7′-, and 7,7′-dibromo-1,1′-binaphthyls together with their trimeric and tetrameric analogues. The coupling of strongly electron-withdrawing 1-CF3-naphthalene provides the 5,5′-disubstituted-1,1′-binaphthyl derivative. The new method does not require the presence of halogen substituents, in contrast to most of the known C-C coupling methods, and it preserves them, if present. Ag(ii)SO4 may be easily electrochemically regenerated from the Ag(i)HSO4 byproduct. However, the C-C coupling method currently suffers from low yields, up to 17%, and it requires further optimization.