102587-98-4

Basic information

• Product Name: 2,7-Dibromopyrene
• Synonyms: 2,7-Dibromopyrene
• CAS NO: 102587-98-4
• Molecular Formula: C₁₆H₈Br₂
• Molecular Weight: 360.04272
• Product Categories: Electronic Chemicals
• Mol File: 102587-98-4.mol

Chemical Properties

• Melting Point: 321°C(lit.)
• Boiling Point: 469.56 °C at 760 mmHg
• Flash Point: 277.277 °C
• Appearance: /
• Density: 1.853 g/cm³
• Vapor Pressure: 1.54E-08mmHg at 25°C
• Refractive Index: 1.863
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Benzene (Very Slightly, Heated), Chloroform (Very Slightly), DMSO (Very Slightly
• CAS DataBase Reference: 2,7-Dibromopyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-Dibromopyrene(102587-98-4)
• EPA Substance Registry System: 2,7-Dibromopyrene(102587-98-4)

Safety Data

• Hazardous Substances Data: 102587-98-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Manufacturing:
2,7-Dibromopyrene is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a valuable component in the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Dye Production:
In the dye industry, 2,7-Dibromopyrene serves as a precursor for the production of dyes with specific color properties. Its chemical composition contributes to the creation of dyes with unique characteristics, suitable for various applications such as textiles, plastics, and printing inks.
Used in Organic Chemical Synthesis:
2,7-Dibromopyrene is employed as a reagent and intermediate in the synthesis of other organic chemicals. Its versatility in chemical reactions makes it a useful building block for creating a wide range of organic compounds for various industrial applications.
Used in Research:
As a research chemical, 2,7-Dibromopyrene is used to study the properties and reactions of PAHs. It aids scientists in understanding the behavior of these compounds under different conditions, which can contribute to the development of new materials and technologies.

InChI:InChI=1/C16H8Br2/c17-13-5-9-1-2-10-6-14(18)8-12-4-3-11(7-13)15(9)16(10)12/h1-8H

Upstream product

• 17533-36-7 2,7-dibromo-4,5,9,10-tetrahydropyrene 
• 129-00-0 pyrene 
• 781-17-9 4,5,9,10-tetrahydropyrene 
• 1714-27-8 2-Bromopyrene 

Downstream Products

• 214622-81-8 pyrene-2,7-dicarboxylic acid 
• 722499-18-5 2,7-bis[N-(4-methoxyphenyl)-N-phenylamino]pyrene 
• 190843-93-7 2,7-di-tert-butyl-pyrene-4,5,9,10-tetraone 

Relevant articles and documents

Dysprosium-carboxylate nanomeshes with tunable cavity size and assembly motif through ionic interactions

We report the design of dysprosium directed metallo-supramolecular architectures on a pristine Cu(111) surface. By an appropriate selection of the ditopic molecular linkers equipped with terminal carboxylic groups (TPA, PDA and TDA species), we create reticular and mononuclear metal-organic nanomeshes of tunable internodal distance, which are stabilized by eight-fold Dy?O interactions. A thermal annealing treatment for the reticular Dy:TDA architecture gives rise to an unprecedented quasi-hexagonal nanostructure based on dinuclear Dy clusters, exhibiting a unique six-fold Dy?O bonding motif. All metallo-supramolecular architectures are stable at room temperature. Our results open new avenues for the engineering of supramolecular architectures on surfaces incorporating f-block elements forming thermally robust nanoarchitectures through ionic bonds.

Synthesis, characterization, and properties of [4]cyclo-2,7-pyrenylene: Effects of cyclic structure on the electronic properties of pyrene oligomers

A cyclic tetramer of pyrene, [4]cyclo-2,7-pyrenylene ([4]CPY), was synthesized from pyrene in six steps and 18% overall yield by the platinum-mediated assembly of pyrene units and subsequent reductive elimination of platinum. The structures of the two key intermediates were unambiguously determined by X-ray crystallographic analysis. DFT calculations showed that the topology of the frontier orbitals in [4]CPY was essentially the same as those in [8]cycloparaphenylene ([8]CPP), and that all the pyrene units were fully conjugated. The electrochemical analyses proved the electronic properties of [4]CPY to be similar to those of [8]CPP. The results are in sharp contrast to those obtained for the corresponding linear oligomers of pyrene in which each pyrene unit was electronically isolated. The results clearly show a novel effect of the cyclic structure on cyclic π-conjugated molecules.

The K-Region in Pyrenes as a Key Position to Activate Aggregation-Induced Emission: Effects of Introducing Highly Twisted N,N-Dimethylamines

A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly twisted N,N-dialkylamines of anthracene and naphthalene induce drastic AIE when these donors are introduced at appropriate positions to stabilize the S1/S0 minimum energy conical intersection (MECI). In the present study, this design strategy was applied to pyrene: the introduction of N,N-dimethylamine substituents at the 4,5-positions of pyrene, the so-called K-region, are likely to stabilize MECIs. To examine this hypothesis, four novel pyrene derivatives, which contain highly twisted N,N-dimethylamino groups at the 4- (4-Py), 4,5- (4,5-Py), 1- (1-Py), or 1,6-positions (1,6-Py) were tested. The nonradiative transitions of 4,5-Py are highly efficient (knr = 57.1 × 107 s-1), so that its fluorescence quantum yield in acetonitrile decreases to φfl = 0.04. The solid-state fluorescence of 4,5-Py is efficient (φfl = 0.49). In contrast, 1,6-Py features strong fluorescence (φfl = 0.48) with a slow nonradiative transition (knr = 11.0 × 107 s-1) that is subject to severe quenching (φfl = 0.03) in the solid state. These results underline that the chemistry of the pyrene K-region is intriguing, both from a photophysical perspective and with respect to materials science.

Molecular compasses and gyroscopes. II. Synthesis and characterization of molecular rotors with axially substituted bis[2-(9-triptycyl)ethynyl]arenes

We have developed a simple convergent procedure for the synthesis of molecular rotors consisting of a central aromatic group coupled with two axially positioned ethynyltriptycenes. Molecular rotors with 1,4-phenylene (1), 1,4′-1,1′-biphenylene (2), 9, 10-anthracenylene (3), and 2,7-pyrenylene (4) groups were prepared by Pd(0)-catalyzed coupling of ethynyl triptycenes with the corresponding dibromoarenes. Although compounds 1-4 were not expected to have free rotation in the solid state, the rotational potentials of 1 and 3 were analyzed by semiempirical methods and the crystal packing of 1 was analyzed to design the structures most likely to yield a functional rotor in the solid state. Semiempirical PM3 calculations predict compounds 1, 2, and 4 to have frictionless internal rotation even at temperatures as low as 25 K, while compound 3 is expected to have a barrier of ca. 4 kcal/mol.

Pyrene-based compound and organic light emitting diode comprising the same

A pyrene-based compound, and an organic light-emitting diode including the pyrene-based compound are provided.

COMPOUND FOR ORGANIC LIGHT EMITTING DIODE, ORGANIC LIGHT EMITTING DIODE HAVING THE SAME, AND DISPLAY APPARATUS HAVING ORGANIC LIGHT EMITTING DIODE

The present disclosure relates to a compound for an organic electronic device represented by chemical formula 1, an organic electronic device including the same, and a display apparatus including the organic electronic device. Details of chemical formula 1 are as defined on the specification. According to the present invention, it is possible to provide the compound for an organic electronic device having excellent performance.COPYRIGHT KIPO 2020

Diarylpyrenes vs. diaryltetrahydropyrenes: Crystal structures, fluorescence, and upconversion photochemistry

The synthesis of two series of substituted 2,7-diaryl-4,5,9,10- tetrahydropyrenes (1a-c) and 2,7-diarylpyrenes (2a-c) is reported; the opposing phenyl tips being terminated with tBu (a), OCH3 (b), or F (c) to impart variation in electronic properties. X-ray crystallographic analysis of the six compounds revealed edge-to-face packing predominately due to van der Waals forces in the solid state in all instances. The photophysical properties of these compounds were investigated in solution and in solid state/thin films. Since the 2,7-bis(4-tert-butylphenyl)tetrahydropyrene 1a possesses unity fluorescence quantum efficiency, it was successfully employed as the emitter in a low power upconversion scheme featuring fac-Ir(ppy) 3 [ppy = 2-phenylpyridine] as the photosensitizer.

COMPOUNDS FOR ELECTRONIC DEVICES

The present invention relates to organic electroluminescent devices comprising compounds of the formula (1), in particular as blue singlet emitting materials in an electroluminescent layer.

Synthesis of 2-and 2,7-functionalized pyrene derivatives: An application of selective C-H borylation

An efficient synthetic route to 2-and 2,7-substituted pyrenes is described. The regiospecific direct C-H borylation of pyrene with an iridium-based catalyst, prepared in situ by the reaction of [{Ir(μ-OMe)cod}2] (cod=1,5-cyclooctadiene) with 4,4′-di-tert-butyl-2,2′-bipyridine, gives 2,7-bis(Bpin)pyrene (1) and 2-(Bpin)pyrene (2, pin=OCMe 2CMe2O). From 1, by simple derivatization strategies, we synthesized 2,7-bis(R)-pyrenes with R=BF3K (3), Br (4), OH (5), B(OH)2 (6), and OTf (7). Using these nominally nucleophilic and electrophilic derivatives as coupling partners in Suzuki-Miyaura, Sonogashira, and Buchwald-Hartwig cross-coupling reactions, we obtained 2,7-bis(R)-pyrenes with R=(4-CO2C8H17)C6H4 (8), Ph (9), Ca≡CPh (10), Ca≡C[{4-B(Mes)2}C 6H4] (11), Ca≡CTMS (12), Ca≡C[(4-NMe 2)C6H4] (14), Ca≡CH (15), N(Ph)[(4-OMe)C6H4] (16), and R=OTf, R′=Ca≡CTMS (13). Lithiation of 4, followed by reaction with CO2, yielded pyrene-2,7-dicarboxylic acid (17), whilst borylation of 2-tBu-pyrene gave 2-tBu-7-Bpin-pyrene (18) selectively. By similar routes (including Negishi cross-coupling reactions), monosubstituted 2-R-pyrenes with R=BF3K (19), Br (20), OH (21), B(OH)2 (22), [4-B(Mes)2]C 6H4 (23), B(Mes)2 (24), OTf (25), Ca≡CPh (26), Ca≡CTMS (27), (4-CO2Me)C6H4 (28), Ca≡CH (29), C3H6CO2Me (30), OC 3H6CO2Me (31), C3H 6CO2H (32), OC3H6CO2H (33), and O(CH2)12Br (34) were obtained from 2. These derivatives are of synthetic and photophysical interest because they contain donor, acceptor, and conjugated substituents. The crystal structures of compounds 4, 5, 7, 12, 18, 19, 21, 23, 26, and 28-31 have also been obtained from single-crystal X-ray diffraction data, revealing a diversity of packing modes, which are described in the Supporting Information. A detailed discussion of the structures of 1 and 2, their polymorphs, solvates, and co-crystals is reported separately. Copyright