1576-69-8

Usage

Chemical Class

Polycyclic aromatic hydrocarbon (PAH)

Structure

Three fused benzene rings

Physical State

Colorless solid at room temperature

Solubility

Insoluble in water, soluble in organic solvents

Uses

Research and development of organic electronic materials (e.g. organic light-emitting diodes and organic photovoltaics), building block for synthesis of new molecules in pharmaceutical and chemical industries

Safety Precautions

Combustible, may cause skin and eye irritation upon contact

InChI:InChI=1/C16H14/c1-11-3-7-15-13(9-11)5-6-14-10-12(2)4-8-16(14)15/h3-10H,1-2H3

Upstream product

• 776-35-2 9,10-dihydrophenanthrene 
• 19399-61-2 2,7-Bis-chlormethyl-9,10-dihydro-phenanthren 
• 698376-80-6 2,7-dimethyl-9-phenanthrol 
• 71871-10-8 2.2'-Bis(chlormethyl)-4.4'-dimethylbiphenyl 
• 2941-83-5 2,7-dimethyl-9,10-dihydrophenanthrene 
• 43012-24-4 2,7-bis(bromomethyl)-9,10-dihydrophenanthrene 

Downstream Products

• 199807-75-5 2,7-Bis-[(Z)-2-(4-bromo-phenyl)-vinyl]-phenanthrene 

Relevant academic research and scientific papers

Regiospecific synthesis of alkylphenanthrenes using a combined directed ortho and remote metalation - Suzuki-Miyaura cross coupling strategy

Using a combined directed ortho metalation (DoM) - Suzuki-Miyaura cross coupling - directed remote metalation (DreM) approach, the alkylphenanthrenes (APs) 1-methyl- (5a), 1,7-dimethyl- (5b), 2,7-dimethyl- (Sc), 7-ethyl-1-methyl- (15), and 7-tert-butyl-1-methylphenanthrenes (27) have been synthesized in four to seven steps and 21%-36% overall yields. In contrast to classical protocols, this method, which may be scaled to gram quantities, provides single isomers of APs in high purity of value as analytical standards for environmental studies. Aminocarbonylation of triflates to N,N-diethylbenzamides (9 → 10) and anionic Fries rearrangement (23 → 24) provide other potential links to DoM chemistry.

Characterization of polycyclic aromatic hydrocarbon particulate and gaseous emissions from polystyrene combustion

The partitioning of polycyclic aromatic hydrocarbons (PAHs) between the particulate and gaseous phases resulting from the combustion of polystyrene was studied. A vertical tubular flow furnace was used to incinerate polystyrene spheres (100-300 μm) at different combustion temperatures (800- 1200 °C) to determine the effect of temperature and polystyrene feed size on the particulate and gaseous emissions and their chemical composition. The furnace reactor exhaust was sampled using real-time instruments (differential mobility particle sizer and/or optical particle counter) to determine the particle size distribution. For chemical composition analyses, the particles were either collected on Teflon filters or split into eight size fractions using a cascade impactor with filter media substrates, while the gaseous products were collected on XAD-2 adsorbent. Gas chromatography/mass spectroscopy (GC/MS) was used to identify and quantify the specific PAH species, their partitioning between the gas and particulate phases, and their distribution as a function of emission particle size. The total mass and number of PAH species in both the particulate and gas phases were found to decrease with increasing incineration temperature and decreasing polystyrene feed size, while the mean diameter of the particles increases with increasing incineration temperature and decreasing feed size. In addition, the PAH species in the particulate phase were found to be concentrated in the smaller aerosol sizes. The experimental results have been analyzed to elucidate the formation mechanisms of PAHs and particles during polystyrene combustion. The implications of these results are also discussed with respect to the control of PAH emissions from municipal waste-to-energy incineration systems. The partitioning of polycyclic aromatic hydrocarbons (PAHs) between particulate and gaseous phases resulting from the combustion of polystyrene was studied. A vertical tubular flow furnace was used to incinerate polystyrene spheres to determine the effect of temperature and polystyrene feed size on the particulate and gaseous emissions and their chemical composition. The furnace reactor exhaust was sampled using real-time instruments to determine the particle size distribution. The total mass and number of PAH species in both the particulate and gas phases were found to decrease with increasing incineration temperature and decreasing polystyrene feed size, while the mean diameter of the particles increases with increasing incineration temperature and decreasing feed size. In addition, the PAH species in the particulate phase were found to be concentrated in the smaller aerosol sizes.

Electron transfer in bis-porphyrin donor-acceptor compounds with polyphenylene spacers shows a weak distance dependence

A series of phenylene-bridged bis-porphyrin adducts have been synthesized, containing one, two, or three phenyl bridges. Complete synthetic details are provided. For studies of photochemical electron transfer, mixed metals wre incorporated, with zinc in one porphyrin macrocycle and FeIII (bis-imidazole) in the other macrocycle. When photoexcited, an electron is transferred from Zn to FeIII. The rate of this process drops only slowly with distance: kα exp(βr), with β = 0.4 A?-1. This dependence can be predicted by a simple theory which assumes that the drop does not reflect increased distance, but rather reflects the break in conjugation which occurs at each phenyl juncture due to the biphenyl twist angle of ca. 50°. Inefficient overlap in this angle results in a rate drop of ca. 6-fold per phenyl ring, in good agreement with the observed results.