Validated analytical strategy for the determination of polycyclic aromatic compounds in marine sediments by liquid chromatography coupled with diode-array detection and mass spectrometry

González-Piñuela, Cristina; Alonso-Salces, Rosa M.; Andrés, A.; Ortiz, Inmaculada; Viguri, Javier R.

doi:10.1016/j.chroma.2006.07.008

Cited by 32 publications

(7 citation statements)

References 34 publications

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“…Triphenylene which is denoted as T a 1 , has the reported experimental λ max in the region of 250 nm [91] . This value is in agreement with the calculated value 258 nm.…”

Section: Resultssupporting

confidence: 85%

Optoelectronic Properties of Polycyclic Benzenoid Hydrocarbons of Various Sizes and Shapes for Donor‐π‐Acceptor Systems: A DFT Study

Rakhi

Suresh

2021

ChemistrySelect

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The zigzag and armchair‐edged benzenoid polycyclic aromatic hydrocarbons (PAHs) possessing circular, parallelogram, rectangular and triangular shapes have been studied for a systematic evaluation of their optoelectronic properties for the design of donor‐π‐acceptor (D‐π‐A) systems using M06L/6‐31+G(d) level of density functional theory (DFT). Molecular electrostatic potential (MESP) analysis of the PAHs is done to characterize their electron distribution while the time‐dependent DFT (TD‐DFT) analysis was used for the absorption spectral analysis. MESP analysis showed Clar's sextet like electronic arrangement in armchair‐edged systems whereas zigzag‐edged ones showed significant electron localization towards the edges. The absorption spectra revealed a linear trend in absorption maximum (λmax) for most of the armchair‐edged systems with respect to the number of π‐electrons. MESP based assessment of the electron rich/deficient features of PAH systems led to the design of PAH‐π‐PAH type D‐π‐A systems wherein a conjugated diene moiety functions as the π‐spacer. The D‐π‐A behaviour of these systems significantly enhanced with the introduction of electron donating functional group NMe2 on donor PAH and electron withdrawing group COOH on the acceptor PAH. The MESP features, frontier molecular orbital (FMO) distribution, and absorption spectral features supported the strong D‐π‐A character of functionalized PAH‐π‐PAH. Among the different shapes studied, the rectangular PAH moiety showed the most efficient tuning of HOMO‐LUMO gap. The optical and electronic properties of PAH, PAH‐π‐PAH and functionalized PAH‐π‐PAH systems suggest the high tunable character of these properties with respect to the size and shape of the PAH.

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“…Triphenylene which is denoted as T a 1 , has the reported experimental λ max in the region of 250 nm [91] . This value is in agreement with the calculated value 258 nm.…”

Section: Resultssupporting

confidence: 85%

Optoelectronic Properties of Polycyclic Benzenoid Hydrocarbons of Various Sizes and Shapes for Donor‐π‐Acceptor Systems: A DFT Study

Rakhi

Suresh

2021

ChemistrySelect

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“…The absorption spectrum for cyclopentatriphenylene 1 (Figure ) has a λ max of 260 nm, which is slightly red-shifted when compared to triphenylene . This is consistent with the electron-donating nature of the 4-methylene bridge decreasing the HOMO–LUMO gap and is supported by the further red-shift when the electron-donating methoxy and tert -butyl groups are introduced.…”

Section: Results and Discussionsupporting

confidence: 63%

Site Selectivity of [RuCp]⁺ Complexation in Cyclopenta[def*]triphenylenes

2014

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A series of new cyclopenta-fused triphenylenes has been synthesized in high yield and reacted with [Ru(μ 3 -Cl)Cp*] 4 to form [RuCp*(η 6 -arene)]PF 6 complexes. Systematic variation of the cyclopenta[def ]triphenylene allowed the site of complexation to be probed and the influence of the electronic and steric properties of the substituents in directing complexation to be assessed. As determined by NMR spectroscopy and X-ray crystallography, in all cases the [RuCp*] + fragment complexes at a peripheral arene ring, rather than at the central arene ring or as a neutral η 5 -cyclopentadienyl metallocene adduct. It was shown that electronic influences are minimal, while steric effects afford selective complexations. The electronic properties of the ligands and complexes were probed with electrochemistry, along with electronic absorption and emission spectroscopies. ■ INTRODUCTIONCyclopentadienyl (Cp, η 5 -C 5 H 5 ) and pentamethylcyclopentadienyl (Cp*, η 5 -C 5 Me 5 ) ruthenium complexes with arene ligands have been extensively studied, forming η 6 -sandwich complexes of the type [RuCp(η 6 -arene)] + and [RuCp*(η 6 -arene)] + that are generally stable under atmospheric conditions. 1−7 The [RuCp*] + fragment is known to strongly interact with aromatic hydrocarbons with a high tolerance to functional groups. 3 The resulting ruthenium sandwich complexes have been studied for their interesting electrochemical and spectroscopic properties, as well as their catalytic activity. 8,9 The most popular synthetic route toward simple [RuCp*(η 6 -arene)] + complexes involves the formation of a [RuCp*-(CH 3 CN) 3 ] + complex, which is reacted with the appropriate arene ligand with heating or UV irradiation. 2,5,10 These methods are generally useful and robust; however, the need for toxic or expensive Sn and Ag reagents leaves room for improvement. In 2007 Fairchild et al. 5 proposed a slightly altered route to these target [RuCp*(η 6 -arene)] + complexes that involves the direct reaction of [Ru(μ 3 -Cl)Cp*] 4 , a precursor in previous pathways, with the arene and the aid of microwave irradiation. The water-soluble chloride salt of the resultant complex was obtained after short reaction times in high yields, and the reaction was shown to be reliable for a wide range of arene ligands. However, the arene ligands studied were mostly single ring benzene derivatives, naphthalene and quinoline being the exceptions, with the [RuCp*] + forced to bind to the only arene ring present.Site selectivity for complexation of [RuCp*] + to substituted polyaromatic systems has been little studied. Previous work 1,6,11,12 gives some precious insight into the affinity of the [RuCp*] + fragment for a range of mostly monosubstituted simple arene systems. Larger polycyclic aromatic hydrocarbon (PAH) ligands that complex [RuCp*] + have all been unsubstituted. 13,14 To the best of our knowledge, no reports to date describe the site selectivity of [RuCp*] + for PAHs with a range of substitution patterns and types. Furthermore, the presence of a peripheral cyc...

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“…Electrospray ionization (ESI), atmospheric-pressure chemical ionization source (APCI), and atmospheric pressure photoionization (APPI) have generally used to ionize PAHs at the LC-MS interface. 122,123 These ionization sources can effectively ionize high-molecularweight PAHs. 124 One study showed that APPI offers at least 3-4 orders of dynamic linear range for PAH analysis under the test conditions.…”

Section: Liquid Chromatography-mass Spectrometry (Lc/lc-ms)mentioning

confidence: 99%

Advances in pretreatment and analysis methods of aromatic hydrocarbons in soil

et al. 2022

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Validated analytical strategy for the determination of polycyclic aromatic compounds in marine sediments by liquid chromatography coupled with diode-array detection and mass spectrometry

Cited by 32 publications

References 34 publications

Optoelectronic Properties of Polycyclic Benzenoid Hydrocarbons of Various Sizes and Shapes for Donor‐π‐Acceptor Systems: A DFT Study

Optoelectronic Properties of Polycyclic Benzenoid Hydrocarbons of Various Sizes and Shapes for Donor‐π‐Acceptor Systems: A DFT Study

Site Selectivity of [RuCp]⁺ Complexation in Cyclopenta[def*]triphenylenes

Advances in pretreatment and analysis methods of aromatic hydrocarbons in soil

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Validated analytical strategy for the determination of polycyclic aromatic compounds in marine sediments by liquid chromatography coupled with diode-array detection and mass spectrometry

Cited by 32 publications

References 34 publications

Optoelectronic Properties of Polycyclic Benzenoid Hydrocarbons of Various Sizes and Shapes for Donor‐π‐Acceptor Systems: A DFT Study

Optoelectronic Properties of Polycyclic Benzenoid Hydrocarbons of Various Sizes and Shapes for Donor‐π‐Acceptor Systems: A DFT Study

Site Selectivity of [RuCp*]+ Complexation in Cyclopenta[def]triphenylenes

Advances in pretreatment and analysis methods of aromatic hydrocarbons in soil

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Site Selectivity of [RuCp]⁺ Complexation in Cyclopenta[def*]triphenylenes