38303-36-5

Usage

Chemical class

Polycyclic aromatic hydrocarbons (PAHs)

Formation

Incomplete combustion of organic materials (coal, wood, and oil)

Toxicity

Highly toxic

Persistence

Persistent organic pollutant

Carcinogenic properties

Known to be carcinogenic

Mutagenic properties

Can cause changes to the DNA of living organisms, including humans

Environmental impact

Potential threat to the environment

Human health impact

Potential threat to human health

Regulation efforts

Efforts being made to regulate and reduce its release into the environment

InChI:InChI=1/C16H7Br3/c17-12-6-2-8-1-3-10-13(18)7-14(19)11-5-4-9(12)15(8)16(10)11/h1-7H

Upstream product

• 129-00-0 pyrene 
• 7726-95-6 bromine 
• 1714-29-0 1-bromopyrene 

Downstream Products

• 916747-36-9 1,3,6-tris(5-tert-butyl-2-methoxyphenyl)pyrene 
• 916747-40-5 1,3,6-tris(5-tert-butyl-2-hydroxyphenyl)pyrene 
• 916747-44-9 1,3,6-tris(5-tert-butyl-2-trifluoromethylsulfonylphenyl)pyrene 
• 1004759-98-1 1,6-bis[Au(PPh₃)]-3-bromopyrene 
• 1032197-91-3 1,3,6-tris[4-(N,N-dimethylamino)phenylethynyl]pyrene 
• 1509916-11-3 1,3,6-tris-(N,N-di-p-methoxyphenylamine)pyrene 

Relevant academic research and scientific papers

Effects of substituents on absorption and fluorescence properties of trimethylsilylethynyl- and tert-butylethynyl-pyrenes

Effects of substituents introduced at 1-position of trimethylsilylethynyl- and tert-butylethynyl-pyrenes on absorption and fluorescence properties were investigated. Fluorescence intensities of 1.0 × 10–5 M CH2Cl2 solutions of these pyrene derivatives were significantly larger than that of pyrene. Absorption of a silyl derivative having a formyl group shifted to longer wavelengths as the solvent polarity increased, whereas that of the carbon analog shifted to shorter wavelengths. On the other hand, in the solvent dependence of fluorescence, both fluorescence of them shifted to longer wavelengths as the polarity of the solvent increased. Fluorescence spectra of pyrene derivatives synthesized in this study at saturated concentrations in CH2Cl2 exhibited excimer emissions in the longer wavelength regions compared to that of unsubstituted pyrene. Fluorescence quantum yields of silicon analogs were higher than that of the corresponding carbon analogs in both solution and solid states. From the results of molecular orbital calculations, it was clarified that the effects of the substituents at the 1-position on the pyrene ring on the absorption and fluorescence properties can be explained by the properties of the molecular orbitals corresponding to the respective electron transitions.

Electron-Transfer-Induced Self-Assembly of a Molecular Tweezer Platform

The design and synthesis of a new molecular tweezer (T-tmp) with electron-rich pincers are reported. The stable monocationic radicals and self-assembled dimeric radicals of this molecular tweezer platform were prepared by chemical oxidative titration. With the aid of DFT calculations, it was found that the dimeric radicals with syn-syn-syn conformer has the most stable structure, with the hole primarily delocalized between parallel stacked pyrenyl groups.

Biphenyl compound and application thereof in preparation of 1, 3, 6-tribromopyrene

The invention discloses a biphenyl compound and application thereof in preparation of 1, 3, 6-tribromopyrene.

The optical properties and quantum chemical calculations of thienyl and furyl derivatives of pyrene

A detailed electrochemical, photophysical and theoretical study is presented for various new thienyl and furyl derivatives of pyrene. Their optical properties are described based on UV-VIS absorption and both steady-state and time-resolved fluorescence spectroscopy. DFT and TDDFT calculations are also presented to support experimental data. The calculations results show that HOMO-LUMO orbitals are delocalized uniformly between aromatic core and aryl substituents. Good electrochemical stability of thienyl and furyl hybrids of pyrene confirm their potential application for light emitting electrochemical cells or spintronics mainly due to their beneficial optical and charge transport properties in electrochromic devices. In order to demonstrate this potential, an OLED device is presented. Synthesized compounds included in this OLED device both facilitate electron transport and act as a light emitting layer.

Furyl derivatives of pyrene: Efficient synthesis and relevant optical properties

A series of various furyl derivatives of pyrene were synthesized by Stille cross-coupling procedure. Their structures were characterized by nuclear magnetic resonance, and elemental analysis. Optical properties of the synthesized materials as well as their energy levels were investigated by ultraviolet-visible absorption supported by fluorescence spectra. All of the studied compounds exhibit fluorescence with energy peaks dependent on the number of furyl substituents. Furthermore, quantum mechanical modeling method of obtained materials are studied. Experimental data are focused on quantum chemical calculations. Highest occupied molecular and lowest unoccupied molecular orbitals are delocalized uniformly on both pyrene core and furyl substituents. Furanyl-pyrene hybrids are potentially good materials for optical applications mainly due to their optical and charge transport properties, which are also desired for electronic applications.

Synthesis and optical properties of various thienyl derivatives of pyrene

A series of various thienyl derivatives of pyrene were synthesized by Stille cross-coupling procedure. Their structures were characterized by 1H NMR, 13C NMR and elemental analysis. The spectroscopic characteristics were investigated by UV-vis absorption and fluorescence spectra. Based on quantum chemical calculations, the energy levels of investigated molecules with respect to the pyrene molecule were also discussed.

CONDENSED-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DIODE INCLUDING THE SAME

Embodiments of the present invention are directed to a condensed-cyclic compound and an OLED including the same.

Synthesis and electro-optical properties of carbazole-substituted pyrene derivatives

Mono and dicarbazole-substituted pyrene derivatives, 9H-carbazol-9-ylpyrene (MCzP) and 1,6-di(9H-carbazol-9-yl)pyrene (DCzP), with dual-purpose function as a blue emitting and charge transporting layer in organic light emitting diodes, were synthesized and characterized. These series of molecules consisted of an electron donating (D) carbazole and an electron accepting (A) pyrene in D-A and D-A-D shapes. Non-doped blue electroluminescent devices with the configurations of ITO (150 nm)/α-NPD (30 nm)/DCzP (40 nm)/LiF (1 nm)/Al (150 nm) (D1) and ITO (150 nm)/2-TNATA (15 nm)/α-NPD (20 nm)/DCzP (40 nm)/BCP (15 nm)/Alq3(10 nm)/LiF (1 nm)/Al (120 nm) (D2) were fabricated. D1 and D2 devices showed blue emission at 492 nm and 488 nm, and maximum luminance of 840 and 7560 cd/m2 obtained at 13 V and 15 V, respectively. 2011 American Scientific Publishers Copyright

Light-emitting device material and light-emitting device

A light emitting device material containing a pyrene compound of formula (1) and a light emitting device. In formula (1), R1 to R18 are the same or different and are selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, arylether, arylthioether, aryl, heteroaryl, halogen, carbonyl, carboxyl, oxycarbonyl, carbamoyl, amino, phosphine oxide and silyl; adjacent substituents among R1 to R18 may be combined with each other to form a ring; n represents an integer of 1 to 3; X is —O—, —S— or —NR19—; R19 is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, aryl, heteroaryl or amino; R19 may be combined with R11 or R18 to form a ring; Y is a single bond, arylene or heteroarylene; and n substituents among R1 to R10 and any one of R11 to R19 are used for linkage with Y

Reaction of polycyclic aromatic hydrocarbons adsorbed on silica in aqueous chlorine

The reaction of polycyclic aromatic hydrocarbons (PAHs) previously adsorbed on silica gel or diatomaceous earth with sodium hypochlorite was carried out to elucidate their reactivity to aqueous chlorine. It was demonstrated that the PAHs adsorbed on silica reacted more rapidly than the PAHs themselves in water, leading to the formation of many chlorinated and oxidized derivatives. A similar reaction in the presence of potassium bromide was found to preferentially produce corresponding brominated derivatives. These reactions seem to proceed through PAHs adsorbed on the silica surface and halogenating agents, the electrophilicity of which may be raised by the catalytic effect of the silanol group of the silica surface. These findings from the environmental viewpoint suggest that the reaction of hydrophobic compounds adsorbed on sediment cannot be neglected.