Anthracene and pyrene photolysis kinetics in aqueous, organic, and mixed aqueous-organic phases

Grossman, Jarod; Stern, Adam P.; Kirich, Makena L.; Kahan, Tara F.

doi:10.1016/j.atmosenv.2015.12.049

Cited by 30 publications

(36 citation statements)

References 38 publications

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“…[10] These models rely on the much discussed hydrogen-abstraction/acetylene-addition (HACA) mechanism, which involves repetitive sequences of atomic hydrogen abstractions from an aromatic hydrocarbon like benzene followed by consecutive addition of one or two acetylene molecule(s) prior to cyclization and aromatization. [11] Interstellar PA Hs can be rapidly destroyed by photolysis, [12] galactic cosmic rays, [13] and interstellar shocks, [10] Scheme 1. Representatives of key classes of PAHs differing by the linear,z igzag, and ortho-condensed arrangements of fused benzene rings:acenes (i), phenacenes (ii), and helicenes (iii).…”

Section: Introductionmentioning

confidence: 99%

A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Zhao

Kaiser

et al. 2020

Angew Chem Int Ed

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A unified low‐temperature reaction mechanism on the formation of acenes, phenacenes, and helicenes—polycyclic aromatic hydrocarbons (PAHs) that are distinct via the linear, zigzag, and ortho‐condensed arrangements of fused benzene rings—is revealed. This mechanism is mediated through a barrierless, vinylacetylene mediated gas‐phase chemistry utilizing tetracene, [4]phenacene, and [4]helicene as benchmarks contesting established ideas that molecular mass growth processes to PAHs transpire at elevated temperatures. This mechanism opens up an isomer‐selective route to aromatic structures involving submerged reaction barriers, resonantly stabilized free‐radical intermediates, and systematic ring annulation potentially yielding molecular wires along with racemic mixtures of helicenes in deep space. Connecting helicene templates to the Origins of Life ultimately changes our hypothesis on interstellar carbon chemistry.

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Section: Introductionmentioning

confidence: 99%

A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Zhao

Kaiser

et al. 2020

Angew Chem Int Ed

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“…1a, 14 Due to the presence of a low energy triplet state combined with efficient intersystem crossing from the singlet to triplet state, pyrene and its derivatives have been previously studied for singlet oxygen generation. 15 NU-1000 16 (Fig. 1a), is a 3-D Zr-based MOF constructed using the tetratopic pyrene-containing linker, 4,4’,4”,4’”-(pyrene-1,3,6,8-tetrayl)tetrabenzoic acid (H 4 TBAPy).…”

Section: Introductionmentioning

confidence: 99%

Efficient and selective oxidation of sulfur mustard using singlet oxygen generated by a pyrene-based metal–organic framework

et al. 2016

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A pyrene-based metal-organic framework (MOF) NU-1000 was used as a heterogeneous photocatalyst for the degradation of a sulfur mustard simulant, 2-chloroethyl ethyl sulfide (CEES). Using irradiation from a commercially available and inexpensive ultraviolet (UV) light-emitting diode (LED), singlet oxygen (1O2) is generated by NU-1000 and selectively oxidizes CEES to the nontoxic product 2-chloroethyl ethyl sulfoxide (CEESO). More importantly, this method was tested on the warfare agent sulfur mustard (HD) for the first time using 1O2 and a MOF catalyst, and this method proved to be effective in oxidizing sulfur mustard to nontoxic products without forming the toxic sulfone by-product.

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“…This is largely due to that IVOCs may have low water solubility or Henry's law coefficient, making it an unlikely effective aqSOA precursor in a theoretical view. Nevertheless, some phenolic carbonyls [14] or polycyclic aromatic hydrocarbon (PAH) compounds [15], which actually belong to the IVOCs category, are found to be effective in producing aqSOA. Very recently, our group also shows that 4-ethylphenol (with a C* in the high-end of IVOCs) [16], naphthoquinone and phenanthrene (both with C* values in the low-end of IVOCs) [17] all have significant aqSOA yields.…”

Section: Introductionmentioning

confidence: 99%

Aqueous-Phase Production of Secondary Organic Aerosols from Oxidation of Dibenzothiophene (DBT)

Liu

Chen

et al. 2020

Atmosphere

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Intermediate-volatility organic compounds (IVOCs) have been recognized as an important contributor to the secondary organic aerosol (SOA) formation via gas-phase reactions. However, it is unclear whether or not IVOCs-SOA can be produced in the aqueous phase. This work investigated aqueous oxidation of one model compound of IVOCs, dibenzothiophene (DBT). Results show that DBT can be degraded by both hydroxyl radical and the triplet excited states of organic light chromophores (3C*). Aqueous dark oxidation of DBT was also possible. SOA yields of 32% and 15% were found for hydroxyl radical (OH)-mediated photo-oxidation and dark oxidation, respectively. A continuous and significant increase of oxidation degree of SOA was observed during OH photo-oxidation, but not during the dark oxidation. Factor analyses revealed that there was a persistent production of highly oxygenated compounds from the less oxygenated species. OH-initiated photochemical reactions can also produce species with a relatively large light-absorbing ability, while such photo-enhancement due to direct light irradiation and 3C*-initiated oxidation could occur, but is much less important. In the future, studies on the second-order rate constants, molecular characterization of the oxidation products from this and other IVOCs precursors are needed to better understand the role of this reaction pathway in SOA budget, air quality and climate change.

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Anthracene and pyrene photolysis kinetics in aqueous, organic, and mixed aqueous-organic phases

Cited by 30 publications

References 38 publications

A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Efficient and selective oxidation of sulfur mustard using singlet oxygen generated by a pyrene-based metal–organic framework

Aqueous-Phase Production of Secondary Organic Aerosols from Oxidation of Dibenzothiophene (DBT)

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