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Synthesis and Reactivity of Novel Aromatic Compounds 2.0
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Synthesis and Reactivity of Novel Aromatic Compounds 2.0

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Physical Chemistry and Chemical Physics".

Deadline for manuscript submissions: closed (20 September 2021) | Viewed by 16086

Special Issue Editors

Prof. Dr. Taku Shoji

E-Mail Website
Guest Editor
Department of Chemistry, Faculty of Science, Shinshu University, 3-1-1, Asahi, Matsumoto, Nagano, Japan
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Tetsuo Okujima

E-Mail Website
Guest Editor
Graduate School of Science and Engineering, Ehime University, Matsuyama, Japan
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

As novel aromatic compounds and related π-electron systems have expanded their application in the field of organic electronics (such as semiconductors, liquid crystals, OLED, etc.) and medicinal chemistry, the establishment of synthetic methods and the elucidation of the reactivity and properties of these derivatives are becoming increasingly important in recent years.

The Special Issue entitled “Synthesis and Reactivity of Novel Aromatic Compounds” will provide a platform for researchers to represent new findings and innovative ideas on the advanced synthesis, reactivity, and applications of novel aromatic compounds and related π-electron systems.

This Special Issue welcomes the submission of original research papers or comprehensive reviews that demonstrate or summarize significant advances in novel aromatic compounds and related π-electron systems in terms of the synthesis, reactivity, properties, and application to functional materials, as well as the bio- and pharmacological activities.

Prof. Dr. Taku Shoji
Prof. Dr. Tetsuo Okujima
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Polycyclic aromatic hydrocarbon (PAHs)
  • Fullerene
  • Calixarene
  • Cyclophane
  • Porphyrin
  • Phthalocyanine
  • Metallacycle
  • Metallocene
  • Troponoid
  • Azulene

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Published Papers (5 papers)

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Research

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16 pages, 3914 KiB  
Article
(2-Hydroxy-3-Methoxybenzylidene)thiazolo[3,2-a]pyrimidines: Synthesis, Self-Assembly in the Crystalline Phase and Cytotoxic Activity
by Artem S. Agarkov, Anna A. Nefedova, Elina R. Gabitova, Dilyara O. Mingazhetdinova, Alexander S. Ovsyannikov, Daut R. Islamov, Syumbelya K. Amerhanova, Anna P. Lyubina, Alexandra D. Voloshina, Igor A. Litvinov, Svetlana E. Solovieva and Igor S. Antipin
Int. J. Mol. Sci. 2023, 24(3), 2084; https://doi.org/10.3390/ijms24032084 - 20 Jan 2023
Cited by 9 | Viewed by 1889
Abstract
A series of new 2-hydroxy-3-methoxybenzylidenethiazolo[3,2-a]pyrimidines with different aryl substituents at the 5 position are synthesized and characterized by 1H/ 13C NMR and IR-spectroscopy and mass-spectrometry, as well as single crystal X-ray diffraction (SCXRD). It was demonstrated that the type [...] Read more.
A series of new 2-hydroxy-3-methoxybenzylidenethiazolo[3,2-a]pyrimidines with different aryl substituents at the 5 position are synthesized and characterized by 1H/ 13C NMR and IR-spectroscopy and mass-spectrometry, as well as single crystal X-ray diffraction (SCXRD). It was demonstrated that the type of hydrogen bonding can play a key role in the chiral discrimination of these compounds in the crystalline phase. The hydrogen bond of the O–H...N type leads to 1D supramolecular heterochiral chains or conglomerate crystallization in the case of the formation of homochiral chains. The hydrogen bond of O–H...O type gave racemic dimers, which are packed into 2D supramolecular layers with a parallel or angular dimers arrangement. Halogen bonding of the N...Br or O...Br type brings a new motif into supramolecular self-assembly in the crystalline phase: the formation of 1D supramolecular homochiral chains instead 2D supramolecular layers. The study of cytotoxicity against various tumor cells in vitro was carried out. It was found that 2-hydroxy−3-methoxybenzylidenethiazolo[3,2-a]pyrimidines with 3-nitrophenyl substituent at C5 carbon atom demonstrated a high efficiency against M-HeLa (cervical adenocarcinoma) and low cytotoxicity against normal liver cells. Full article
(This article belongs to the Special Issue Synthesis and Reactivity of Novel Aromatic Compounds 2.0)
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20 pages, 3121 KiB  
Article
Thiacalixarenes with Sulfur Functionalities at Lower Rim: Heavy Metal Ion Binding in Solution and 2D-Confined Space
by Anton Muravev, Ayrat Yakupov, Tatiana Gerasimova, Daut Islamov, Vladimir Lazarenko, Alexander Shokurov, Alexander Ovsyannikov, Pavel Dorovatovskii, Yan Zubavichus, Alexander Naumkin, Sofiya Selektor, Svetlana Solovieva and Igor Antipin
Int. J. Mol. Sci. 2022, 23(4), 2341; https://doi.org/10.3390/ijms23042341 - 20 Feb 2022
Cited by 8 | Viewed by 2474
Abstract
Sulfur-containing groups preorganized on macrocyclic scaffolds are well suited for liquid-phase complexation of soft metal ions; however, their binding potential was not extensively studied at the air–water interface, and the effect of thioether topology on metal ion binding mechanisms under various conditions was [...] Read more.
Sulfur-containing groups preorganized on macrocyclic scaffolds are well suited for liquid-phase complexation of soft metal ions; however, their binding potential was not extensively studied at the air–water interface, and the effect of thioether topology on metal ion binding mechanisms under various conditions was not considered. Herein, we report the interface receptor characteristics of topologically varied thiacalixarene thioethers (linear bis-(methylthio)ethoxy derivative L2, O2S2-thiacrown-ether L3, and O2S2-bridged thiacalixtube L4). The study was conducted in bulk liquid phase and Langmuir monolayers. For all compounds, the highest liquid-phase extraction selectivity was revealed for Ag+ and Hg2+ ions vs. other soft metal ions. In thioether L2 and thiacalixtube L4, metal ion binding was evidenced by a blue shift of the band at 303 nm (for Ag+ species) and the appearance of ligand-to-metal charge transfer bands at 330–340 nm (for Hg2+ species). Theoretical calculations for thioether L2 and its Ag and Hg complexes are consistent with experimental data of UV/Vis, nuclear magnetic resonance (NMR) spectroscopy, and single-crystal X-ray diffractometry of Ag–thioether L2 complexes and Hg–thiacalixtube L4 complex for the case of coordination around the metal center involving two alkyl sulfide groups (Hg2+) or sulfur atoms on the lower rim and bridging unit (Ag+). In thiacrown L3, Ag and Hg binding by alkyl sulfide groups was suggested from changes in NMR spectra upon the addition of corresponding salts. In spite of the low ability of the thioethers to form stable Langmuir monolayers on deionized water, one might argue that the monolayers significantly expand in the presence of Hg salts in the water subphase. Hg2+ ion uptake by the Langmuir–Blodgett (LB) films of ligand L3 was proved by X-ray photoelectron spectroscopy (XPS). Together, these results demonstrate the potential of sulfide groups on the calixarene platform as receptor unit towards Hg2+ ions, which could be useful in the development of Hg2+-selective water purification systems or thin-film sensor devices. Full article
(This article belongs to the Special Issue Synthesis and Reactivity of Novel Aromatic Compounds 2.0)
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13 pages, 2234 KiB  
Article
Antioxidant Potential of Aqueous Dispersions of Fullerenes C60, C70, and Gd@C82
by Ivan V. Mikheev, Madina M. Sozarukova, Dmitry Yu. Izmailov, Ivan E. Kareev, Elena V. Proskurnina and Mikhail A. Proskurnin
Int. J. Mol. Sci. 2021, 22(11), 5838; https://doi.org/10.3390/ijms22115838 - 29 May 2021
Cited by 17 | Viewed by 3547
Abstract
The antioxidant potential (capacity and activity) of aqueous fullerene dispersions (AFD) of non-functionalized C60, C70, and Gd@C82 endofullerene (in micromolar concentration range) was estimated based on chemiluminescence measurements of the model of luminol and generation of organic radicals [...] Read more.
The antioxidant potential (capacity and activity) of aqueous fullerene dispersions (AFD) of non-functionalized C60, C70, and Gd@C82 endofullerene (in micromolar concentration range) was estimated based on chemiluminescence measurements of the model of luminol and generation of organic radicals by 2,2′-azobis(2-amidinopropane) dihydrochloride (ABAP). The antioxidant capacity was estimated by the TRAP method, from the concentration of half-suppression, and from the suppression area in the initial period. All three approaches agree and show that the antioxidant capacity of AFDs increased in the order Gd@C82 < C70 < C60. Mathematical modeling of the long-term kinetics data was used for antioxidant activity estimation. The effect of C60 and C70 is found to be quenching of the excited product of luminol with ABAP-generated radical and not an actual antioxidant effect; quenching constants differ insignificantly. Apart from quenching with a similar constant, the AFD of Gd@C82 exhibits actual antioxidant action. The antioxidant activity in Gd@C82 is 300-fold higher than quenching constants. Full article
(This article belongs to the Special Issue Synthesis and Reactivity of Novel Aromatic Compounds 2.0)
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23 pages, 3804 KiB  
Article
Switching Ion Binding Selectivity of Thiacalix[4]arene Monocrowns at Liquid–Liquid and 2D-Confined Interfaces
by Anton Muravev, Ayrat Yakupov, Tatiana Gerasimova, Ramil Nugmanov, Ekaterina Trushina, Olga Babaeva, Guliya Nizameeva, Viktor Syakaev, Sergey Katsyuba, Sofiya Selektor, Svetlana Solovieva and Igor Antipin
Int. J. Mol. Sci. 2021, 22(7), 3535; https://doi.org/10.3390/ijms22073535 - 29 Mar 2021
Cited by 4 | Viewed by 3062
Abstract
Understanding the interaction of ions with organic receptors in confined space is of fundamental importance and could advance nanoelectronics and sensor design. In this work, metal ion complexation of conformationally varied thiacalix[4]monocrowns bearing lower-rim hydroxy (type I), dodecyloxy (type II), or methoxy (type [...] Read more.
Understanding the interaction of ions with organic receptors in confined space is of fundamental importance and could advance nanoelectronics and sensor design. In this work, metal ion complexation of conformationally varied thiacalix[4]monocrowns bearing lower-rim hydroxy (type I), dodecyloxy (type II), or methoxy (type III) fragments was evaluated. At the liquid–liquid interface, alkylated thiacalixcrowns-5(6) selectively extract alkali metal ions according to the induced-fit concept, whereas crown-4 receptors were ineffective due to distortion of the crown-ether cavity, as predicted by quantum-chemical calculations. In type-I ligands, alkali-metal ion extraction by the solvent-accessible crown-ether cavity was prevented, which resulted in competitive Ag+ extraction by sulfide bridges. Surprisingly, amphiphilic type-I/II conjugates moderately extracted other metal ions, which was attributed to calixarene aggregation in salt aqueous phase and supported by dynamic light scattering measurements. Cation–monolayer interactions at the air–water interface were monitored by surface pressure/potential measurements and UV/visible reflection–absorption spectroscopy. Topology-varied selectivity was evidenced, towards Sr2+ (crown-4), K+ (crown-5), and Ag+ (crown-6) in type-I receptors and Na+ (crown-4), Ca2+ (crown-5), and Cs+ (crown-6) in type-II receptors. Nuclear magnetic resonance and electronic absorption spectroscopy revealed exocyclic coordination in type-I ligands and cation–π interactions in type-II ligands. Full article
(This article belongs to the Special Issue Synthesis and Reactivity of Novel Aromatic Compounds 2.0)
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Review

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35 pages, 49504 KiB  
Review
Synthesis of Azulene Derivatives from 2H-Cyclohepta[b]furan-2-ones as Starting Materials: Their Reactivity and Properties
by Taku Shoji, Shunji Ito and Masafumi Yasunami
Int. J. Mol. Sci. 2021, 22(19), 10686; https://doi.org/10.3390/ijms221910686 - 1 Oct 2021
Cited by 20 | Viewed by 4212
Abstract
A variety of synthetic methods have been developed for azulene derivatives due to their potential applications in pharmaceuticals and organic materials. Particularly, 2H-cyclohepta[b]furan-2-one and its derivatives have been frequently used as promising precursors for the synthesis of azulenes. In [...] Read more.
A variety of synthetic methods have been developed for azulene derivatives due to their potential applications in pharmaceuticals and organic materials. Particularly, 2H-cyclohepta[b]furan-2-one and its derivatives have been frequently used as promising precursors for the synthesis of azulenes. In this review, we describe the development of the synthesis of azulenes by the reaction of 2H-cyclohepta[b]furan-2-ones with olefins, active methylenes, enamines, and silyl enol ethers as well as their reactivity and properties. Full article
(This article belongs to the Special Issue Synthesis and Reactivity of Novel Aromatic Compounds 2.0)
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