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Polycyclic Aromatic Hydrocarbons: Synthesis, Characterisation and Application

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (20 January 2019) | Viewed by 12151

Special Issue Editor


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Guest Editor
Univ Rennes, CNRS, Institut des Sciences Chimiques de Rennes, Rennes, France
Interests: π-conjugated systems; polycyclic aromatic hydrocarbons; organophosphorus; heterochemistry; dyes; opto-electronic devices; hybrid materials

Special Issue Information

Dear Colleagues,

Polycyclic aromatic hydrocarbons (PAHs) are organic molecules featuring a bidimensional backbone composed of sp2-C atoms. This particular chemical structure confers to PAHs unique properties in term of reactivity, optical/redox properties, self-assembly and (opto)-electronic device performances. Furthermore, with the rise of graphene-based materials, PAHs appear as key building-blocks for the “total synthesis” of monodispersed nanographenes.

The continuous development of PAHs results in the synergy of advanced organic synthesis, spectroscopy, theoretical chemistry, supramolecular chemistry and electronic engineering. The present special issue “Polycyclic Aromatic Hydrocarbons: Synthesis, Characterizations and Applications” aims at covering all these aspects linked to these fascinating molecules.

Dr. Pierre-Antoine Bouit
Guest Editor

Manuscript Submission Information

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Keywords

  • Molecular engineering
  • Polycycles
  • Nanographenes
  • Catalysis
  • Heterocycles
  • Absorption/Fluorescence
  • Redox activity
  • Supramolecular chemistry
  • Theoretical chemistry
  • Devices

Published Papers (3 papers)

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Research

9 pages, 1653 KiB  
Article
Dyeing Method and Properties of a Novel Blue Azo-Anthraquinone Reactive Dye on Cotton
by Bin Shan, Wei Xiong and Shufen Zhang
Molecules 2019, 24(7), 1334; https://doi.org/10.3390/molecules24071334 - 04 Apr 2019
Cited by 10 | Viewed by 3515
Abstract
A novel blue azo-anthraquinone reactive dye was evaluated in the dyeing of cotton by using a dip–pad–steam process. Dyeing method and properties were examined in detail and the results showed that the dyeing method consisting of dye concentration of 25 g/L, sodium carbonate [...] Read more.
A novel blue azo-anthraquinone reactive dye was evaluated in the dyeing of cotton by using a dip–pad–steam process. Dyeing method and properties were examined in detail and the results showed that the dyeing method consisting of dye concentration of 25 g/L, sodium carbonate of 12 g/L, dipping time of 3 min and steaming time of 30 min was the most effective when a conventional “one-dip–one-nip” process was used. The fixation of the dyes on cotton could reach up to 93.4%, the wash and rub fastness both reached grade 4 above, and the light fastness reached grade 4–5 above. Such colored cotton showed very close colorimetric properties. Full article
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8 pages, 1217 KiB  
Article
Synthesis of Aromatic Rings Embedded in Polycyclic Scaffolds by Triyne Cycloaddition: Competition between Carbonylative and Non-Carbonylative Pathways
by Laura Salacz, Nicolas Girard, Jean Suffert and Gaëlle Blond
Molecules 2019, 24(3), 595; https://doi.org/10.3390/molecules24030595 - 07 Feb 2019
Cited by 2 | Viewed by 2825
Abstract
Cycloadditions have emerged as some of the most useful reactions for the formation of polycyclic compounds. The carbonylative cycloaddition of triynes can lead to carbonylative and non-carbonylative competitive pathways, each leading to the formation of an aromatic ring. We report herein the one-pot [...] Read more.
Cycloadditions have emerged as some of the most useful reactions for the formation of polycyclic compounds. The carbonylative cycloaddition of triynes can lead to carbonylative and non-carbonylative competitive pathways, each leading to the formation of an aromatic ring. We report herein the one-pot synthesis of fully- and unsymmetrically-substituted tetracyclic 6,5,7,5-troponic and 6,5,6,5-benzenoid scaffolds using pre-organized triynes showing the competition between these two pathways. Full article
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10 pages, 2442 KiB  
Article
Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties
by Otohiro Gotsu, Tomomi Shiota, Hiroki Fukumoto, Tomoko Kawasaki-Takasuka, Takashi Yamazaki, Tomoko Yajima, Tomohiro Agou and Toshio Kubota
Molecules 2018, 23(12), 3337; https://doi.org/10.3390/molecules23123337 - 16 Dec 2018
Cited by 7 | Viewed by 5254
Abstract
Intramolecular photocyclization of stilbene derivatives (Mallory reaction) is one of the efficient methods for building polycyclic aromatic hydrocarbon (PAH) frameworks, and is also expected to be applicable to synthesis of fluorine-containing PAHs (F-PAHs). In this study, dibenzoanthracene-type (4a) and benzoperylene-type ( [...] Read more.
Intramolecular photocyclization of stilbene derivatives (Mallory reaction) is one of the efficient methods for building polycyclic aromatic hydrocarbon (PAH) frameworks, and is also expected to be applicable to synthesis of fluorine-containing PAHs (F-PAHs). In this study, dibenzoanthracene-type (4a) and benzoperylene-type (4b) F-PAHs were synthesized using the Mallory reaction of the 1,4-distyrylbenzene-type π-conjugated molecule (3a), which was prepared by addition-defluorination of available octafluorocyclopentene (OFCP) and aryllithium in three steps. The structure of 4a originating from π–π interaction was characterized by X-ray crystallographic analysis. The absorption maxima of UV-Vis spectra and emission maxima of photoluminescence spectra of the PAHs were positioned at a longer wavelength compared to those of the corresponding unsubstituted PAHs, presumably due to the electron-withdrawing nature of perfluorocyclopentene (PFCP) units. The effect of PFCP units in F-PAHs was also studied by time-dependent density functional theory (TD-DFT) calculation. Full article
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