scholarly journals Diels–Alder Cycloaddition to the Bay Region of Perylene and Its Derivatives as an Attractive Strategy for PAH Core Expansion: Theoretical and Practical Aspects

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5373
Author(s):  
Aneta Kurpanik ◽  
Marek Matussek ◽  
Piotr Lodowski ◽  
Grażyna Szafraniec-Gorol ◽  
Michał Krompiec ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Organic Synthesis ◽  
Aromatic Hydrocarbons ◽  
Theoretical Calculations ◽  
Modern Technology ◽  
Diels Alder ◽  
Point Of View ◽  
Synthetic Method ◽  
Polycyclic Aromatics ◽  
Polycyclic Aromatic

PAHs (polycyclic aromatics hydrocarbons), the compound group that contains perylene and its derivatives, including functionalized ones, have attracted a great deal of interest in many fields of science and modern technology. This review presents all of the research devoted to modifications of PAHs that are realized via the Diels–Alder (DA) cycloaddition of various dienophiles to the bay regions of PAHs, leading to the π-extension of the starting molecule. This type of annulative π-extension (APEX) strategy has emerged as a powerful and efficient synthetic method for the construction of polycyclic aromatic hydrocarbons and their functionalized derivatives, nanographenes, and π-extended fused heteroarenes. Then, [4 + 2] cycloadditions of ethylenic dienophiles, -N=N-, i.e., diazo-dienophiles and acetylenic dienophiles, are presented. This subject is discussed from the organic synthesis point of view but supported by theoretical calculations. The possible applications of DA cycloaddition to PAH bay regions in various science and technology areas, and the prospects for the development of this synthetic method, are also discussed.

Selective dealkylation of alkyl polycyclic aromatic hydrocarbons towards innovative upgrading process of practical heavy oil

2021 ◽  
Author(s):  
Fumiya Nakano ◽  
Tomohide Goma ◽  
Satoshi Suganuma ◽  
Etsushi Tsuji ◽  
Naonobu Katada
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Pore Size ◽  
Aromatic Hydrocarbons ◽  
Heavy Oil ◽  
Acid Sites ◽  
Polycyclic Aromatics ◽  
Large Pore ◽  
Polycyclic Aromatic ◽  
Long Chain ◽  
Large Pore Size

A silica-monolayer loaded on alumina with weak Brønsted acid sites and large pore size can selectively dealkylate alkyl polycyclic aromatics to long-chain alkanes and polycyclic aromatics for production of chemicals and fuel.

scholarly journals Insights into carbon-nanotube-assisted electrooxidation of polycyclic aromatic hydrocarbons for mediated bioelectrocatalysis

2021 ◽  
Author(s):  
Paulo Henrique Maciel Buzzetti ◽  
Pierre-Yves Blanchard ◽  
Emerson Marcelo Girotto ◽  
Yuta Nishina ◽  
Serge Cosnier ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Carbon Nanotube ◽  
Aromatic Hydrocarbons ◽  
Polycyclic Aromatics ◽  
Π Stacking ◽  
Polycyclic Aromatic ◽  
Mediated Bioelectrocatalysis

A series of polycyclic aromatics, naphthalene, phenanthrene, perylene, pyrene, 1-pyrenebutyric acid N-hydroxysuccinimide ester (pyrene NHS) and coronene, were immobilized via π stacking on carbon nanotube (CNT) electrodes and electro-oxidized in...

Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 211-222
Author(s):  
Junzhi Liu ◽  
Xinliang Feng
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Organic Synthesis ◽  
Aromatic Hydrocarbons ◽  
Efficient Method ◽  
Dipolar Cycloaddition ◽  
Bottom Up ◽  
Nitrogen Doped ◽  
Synthesis Strategy ◽  
Polycyclic Aromatic ◽  
Boron Nitrogen

Bottom-up organic synthesis serves as an efficient method to provide atomically precise heteroatom-doped polycyclic aromatic hydrocarbons (PAHs) with not only well-defined size and edge structures but also specific concentrations and positions of the heteroatoms. We provide a plenary account of the preparation of nitrogen-doped PAHs (N-PAHs) through 1,3-dipolar cycloaddition between different dipolarophiles, as well as pyrazine-type N-doped diaza-hexa-peri-hexabenzocoronene (diaza-HBC). Additionally, we present the synthesis of a class of helical N-charged PAHs, including one charged aza[5]helicene and two charged aza[4]helicenes. Moreover, the bottom-up organic synthesis strategy is further extended to the construction of novel nitrogen-boron-nitrogen (NBN)-containing PAHs. Finally, we discuss the synthesis of four-coordinate boron chromophores containing 6,12,18-tris(alkyl amine)-5,11,17-triazatrinaphthylene derivative ligands.1 Introduction2 Nitrogen-Doped PAHs Based on Dibenzo-9a-azaphenalene (DBAP)3 Cationic Nitrogen-Doped Helical PAHs4 Nitrogen–Boron–Nitrogen-Doped PAHs5 Conclusion and Outlook

On the formation of phosphorous polycyclic aromatics hydrocarbons (PAPHs) in astrophysical environments

2019 ◽  
Vol 21 (15) ◽  
pp. 8015-8021 ◽  
Author(s):  
Marco Fioroni ◽  
Robert E. Savage ◽  
Nathan J. DeYonker
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Polycyclic Aromatics ◽  
Polycyclic Aromatic

CP radical astrochemistry. An important molecule in the synthesis of phosphorous polycyclic aromatic hydrocarbons (PAPH).

Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds

2019 ◽  
Author(s):  
Evan Darzi ◽  
Joyann Barber ◽  
Neil Garg
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Polycyclic Aromatic Hydrocarbon ◽  
Aromatic Hydrocarbon ◽  
Aromatic Hydrocarbons ◽  
Diels Alder ◽  
Pericyclic Reactions ◽  
One Pot ◽  
Synthetic Strategy ◽  
Polycyclic Aromatic

We report a modular synthetic strategy for accessing heteroatom-containing polycyclic aromatic hydrocarbons (PAHs) that relies on the controlled generation of transient heterocyclic alkynes and arynes. The strained intermediates undergo in situ trapping with readily accessible oxadiazinones. Four sequential pericyclic reactions occur, namely two Diels–Alder / retro-Diels–Alder sequences, which can be performed in a stepwise or one-pot fashion to assemble four new carbon–carbon (C–C) bonds.

Eine PMO-theoretische Untersuchung der benzogenen Diels-Alder-Reaktion polycyclischer aromatischer Kohlenwasserstoffe / APMO-theoretical Treatment of the Benzogenic Diels-Alder Reaction of Polycyclic Arom atic Hydrocarbons

1978 ◽  
Vol 33 (11) ◽  
pp. 1395-1397
Author(s):  
M. Zander
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Maleic Anhydride ◽  
Aromatic Hydrocarbons ◽  
Reaction Rates ◽  
Alder Reaction ◽  
Diels Alder ◽  
Orbital Method ◽  
Theoretical Treatment ◽  
Diels Alder Reaction ◽  
Polycyclic Aromatic

Experimental reaction rates of the benzogenic Diels- Alder reaction of polycyclic aromatic hydrocarbons with maleic anhydride are correlated with the corresponding bislocalization energies calculated by the PMO method. The observed relations between the localization energies of the reacting centres and the topology of the hydrocarbons can be qualitatively understood on the basis of Clar’s π-sextet model of polycyclic systems and Polansky’s pars orbital method.

Sign in / Sign up

Export Citation Format

Share Document