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Current Problems of the Organic Chemistry of Sulfur and Selenium
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Current Problems of the Organic Chemistry of Sulfur and Selenium

A special issue of Materials (ISSN 1996-1944). This special issue belongs to the section "Materials Chemistry".

Deadline for manuscript submissions: closed (30 September 2020) | Viewed by 22514

Special Issue Editors

Prof. Dr. Grzegorz Mlostoń

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Guest Editor
Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Łódź, Poland
Interests: organic synthesis; organic chemistry of sulfur; organic chemistry of fluorine; organic reactions mechanisms; sulfur containing functional materials; homogenous catalysis; drug synthesis and drug delivery
Special Issues, Collections and Topics in MDPI journals
Prof. Jarosław Lewkowski

E-Mail Website1 Website2
Guest Editor
University of Lodz, Faculty of Chemistry, Department of Organic Chemistry, Tamka 12, 91-403 Łódź, Poland
Interests: organic chemistry; organic asymmetric synthesis; chemistry of furans; chemistry of ferrocenes; chemistry of aminophosphonic systems; chemistry of anticancer agents; selective oxidation of organic compounds; organic electrosynthesis; ecotoxicology; pesticides and biocides
Prof. Dr. Jarosław Romański

E-Mail Website1 Website2
Guest Editor
Department of Organic and Applied Chemistry, University of Lodz, Tamka 12, 91-403 Łódź, Poland
Interests: organic chemistry; heterocycles; macrocycles; crown ethers; cycloaddition; click chemistry; reactive intermediates; organosulfur chemistry; organic synthesis; reactions mechanisms; flash vacuum pyrolysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Sulfur- and/or selenium-containing organic compounds, including polymers and materials displaying special properties, are of great importance in both academic, basic research and for large scale industrial applications. Sulfur belongs to a narrow group of elements that appear both in bound and non-bound forms. For this reason, sulfur and its compounds accompany people in diverse activities that have been developed for many centuries. Selenium is less common and only appears in the bound form.

Organic synthesis based on sulfur compounds has been intensively developed and sulfur-containing functional groups are known, for example, as useful auxiliaries for asymmetric synthesis. Catalytic reactions with sulfur catalysts have been developed for decades and so-called thiourea organocatalysis belongs to the most modern and powerful strategies applied in organic synthesis. Sulfur-containing functional groups are crucial for mechanisms governing organic reactions and the importance of the sulfur atom for the switch from a concerted to step-wise mechanism in cycloaddition reactions is a problem of current experimental and computational studies.

In our times, sulfur- and/or selenium-based organic and inorganic materials play a leading role in the development of new energy sources. Material scientists are developing both organic and inorganic sulfur compounds as new, non-metallic, low-temperature superconducting materials; one known example is ‘quantum dots’, which are finding more and more applications in the construction of the modern generation of computers.

Remarkable progress has been observed in sulfur-based polymer chemistry. For example, copolymerization of liquid sulfur with 1,3-di-isopropenylbenzene in the absence of any organic solvent is of great interest as a method for the preparation of a stable copolymer that can be cast in molds and also forms a transparent glass.

Sulfur is an important component of all living cells since cysteine, methionine, and homocysteine belong to the group of naturally-occuring amino acids. During the last century, the medical sciences developed numerous drugs that contain sulfur as an important element of the organic molecule. Most of them belong to the class of aromatic or non-aromatic sulfur heterocycles. Similarly, selenium has been demonstrated as an important component of many medicinally-important compounds. Today, scientists are in search of natural and synthetic sulfur and selenium compounds for new medicines.

The announced Special Issue is open for research related to current studies performed in chemical laboratories involving sulfur- and/or selenium-containing compounds. The works resulting from this research, aimed either at the solution of basic, mechanistic problems or at synthetically relevant questions of practical importance, are welcome. The Special Issue is open for submissions until 31 October, 2019.

Prof. Grzegorz Mlostoń
Prof. Jarosław Lewkowski
Prof. Jarosław Romański
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. Materials is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2600 CHF (Swiss Francs). 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

  • Organic synthesis based on the application of sulfur and/or selenium compounds 
  • Synthesis of new sulfur- and/or selenium-containg compounds including heterocycles with a diverse ring size 
  • Asymmetric synthesis with sulfur auxiliaries and sulfur-containing ligands 
  • Catalytic reactions with sulfur-containing catalysts and organocatalysts 
  • Sulfur- and/or selenium-containing natural products and biologically active compounds 
  • Sulfur- and/or selenium-containing compounds in material chemistry 
  • Mechanisms of organic reactions involving sulfur or selenium as important reaction centers

Published Papers (9 papers)

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Editorial

Jump to: Research, Review

2 pages, 606 KiB  
Editorial
In Memoriam: Professor Jarosław Lewkowski (1966–2019)
by Grzegorz Mlostoń and Jarosław Romański
Materials 2020, 13(18), 4030; https://doi.org/10.3390/ma13184030 - 11 Sep 2020
Viewed by 1425
Abstract
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(This article belongs to the Special Issue Current Problems of the Organic Chemistry of Sulfur and Selenium)

Research

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12 pages, 1385 KiB  
Article
Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton—Synthesis and Antiproliferative Activity
by Dominika Iwan, Karolina Kamińska, Elżbieta Wojaczyńska, Mateusz Psurski, Joanna Wietrzyk and Marek Daszkiewicz
Materials 2020, 13(21), 5010; https://doi.org/10.3390/ma13215010 - 06 Nov 2020
Cited by 7 | Viewed by 1720
Abstract
In a search for new, selective antitumor agents, we prepared a series of sulfonamides built on bicyclic scaffolds of 2-azabicyclo(2.2.1)heptane and 2-azabicyclo(3.2.1)octane. To this end, aza-Diels–Alder cycloadducts were converted into amines bearing 2-azanorbornane or a bridged azepane skeleton; their treatment with sulfonyl [...] Read more.
In a search for new, selective antitumor agents, we prepared a series of sulfonamides built on bicyclic scaffolds of 2-azabicyclo(2.2.1)heptane and 2-azabicyclo(3.2.1)octane. To this end, aza-Diels–Alder cycloadducts were converted into amines bearing 2-azanorbornane or a bridged azepane skeleton; their treatment with sulfonyl chlorides containing biaryl moieties led to the title compounds. The study of antiproliferative activity of the new agents showed that some of them inhibited the growth of chosen cell lines with the IC50 values comparable with cisplatin, and some derivatives were found considerably less toxic for nonmalignant cells. Full article
(This article belongs to the Special Issue Current Problems of the Organic Chemistry of Sulfur and Selenium)
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14 pages, 2696 KiB  
Article
Effect of Aromatic System Expansion on Crystal Structures of 1,2,5-Thia- and 1,2,5-Selenadiazoles and Their Quaternary Salts: Synthesis, Structure, and Spectroscopic Properties
by Jan Alfuth, Beata Zadykowicz, Artur Sikorski, Tadeusz Połoński, Katarzyna Eichstaedt and Teresa Olszewska
Materials 2020, 13(21), 4908; https://doi.org/10.3390/ma13214908 - 31 Oct 2020
Cited by 7 | Viewed by 1988
Abstract
Rational manipulation of secondary bonding interactions is a crucial factor in the construction of new chalcogenadiazole-based materials. This article reports detailed experimental studies on phenanthro[9,10-c][1,2,5]chalcogenadiazolium and 2,1,3-benzochalcogenadiazolium salts and their precursors. The compounds were synthesized, characterized employing NMR and UV-Vis spectroscopy. [...] Read more.
Rational manipulation of secondary bonding interactions is a crucial factor in the construction of new chalcogenadiazole-based materials. This article reports detailed experimental studies on phenanthro[9,10-c][1,2,5]chalcogenadiazolium and 2,1,3-benzochalcogenadiazolium salts and their precursors. The compounds were synthesized, characterized employing NMR and UV-Vis spectroscopy. TD-DFT calculations were also performed. The influence of the size of the aromatic system on the molecular motifs formed by the compounds in the solid state has been studied by means of single-crystal X-ray diffraction. In case of the salts, the nature of an anion was also taken into consideration. The results show that cyclic [E···N]2 supramolecular synthon connects neighboring molecules of phenanthro[9,10-c][1,2,5]chalcogenadiazoles, with a relatively large aromatic system, in dimers regardless of the chalcogen atom in the molecule. Both N-methyl-2,1,3-benzothiadiazolium and N-methylphenanthro[9,10-c][1,2,5]chalcogenadiazolium cations have a strong affinity for triflate and iodide anions, therefore the formation of S···N or Se···N secondary bonding interactions is observed only in two out of the eight quaternary salts. Less coordinating anions must be used to enable the building blocks studied to form cyclic [E···N]2 synthons. Moreover, for two of the triflate salts, which are isostructural, a new supramolecular motif has been observed. Full article
(This article belongs to the Special Issue Current Problems of the Organic Chemistry of Sulfur and Selenium)
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11 pages, 1546 KiB  
Communication
Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles
by Justyna Doroszuk, Mateusz Musiejuk, Bartosz Jędrzejewski, Juliusz Walczak and Dariusz Witt
Materials 2020, 13(20), 4492; https://doi.org/10.3390/ma13204492 - 10 Oct 2020
Cited by 1 | Viewed by 1868
Abstract
A simple, efficient, and practical sulfenylation at the C2 position of N-tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of N-tosylindoles with BuLi and S-alkyl, and S-aryl phosphorodithioates or thiotosylates to produce 2-sulfenylindoles [...] Read more.
A simple, efficient, and practical sulfenylation at the C2 position of N-tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of N-tosylindoles with BuLi and S-alkyl, and S-aryl phosphorodithioates or thiotosylates to produce 2-sulfenylindoles in moderate to high yields. The presence of additional hydroxy, carboxy, or amino functionalities did not disturb the formation of products. Full article
(This article belongs to the Special Issue Current Problems of the Organic Chemistry of Sulfur and Selenium)
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19 pages, 3902 KiB  
Article
Anionic Copolymerization of Styrene Sulfide with Elemental Sulfur (S8)
by Jakub Wręczycki, Dariusz M. Bieliński, Marcin Kozanecki, Paulina Maczugowska and Grzegorz Mlostoń
Materials 2020, 13(11), 2597; https://doi.org/10.3390/ma13112597 - 07 Jun 2020
Cited by 23 | Viewed by 3441
Abstract
The superior ability of thiiranes (episulfides) to undergo ring-opening polymerization (ROP) in the presence of anionic initiators allows the preparation of chemically stable polysulfide homopolymers. Incorporation of elemental sulfur (S8) by copolymerization below the floor temperature of S8 permits the [...] Read more.
The superior ability of thiiranes (episulfides) to undergo ring-opening polymerization (ROP) in the presence of anionic initiators allows the preparation of chemically stable polysulfide homopolymers. Incorporation of elemental sulfur (S8) by copolymerization below the floor temperature of S8 permits the placement of a large quantity of sulfur atoms in the polysulfide mainchain. The utility of styrene sulfide (2-phenylthiirane; StS) for copolymerization with elemental sulfur is reported here. A few polysulfides differing depending on the initial ratio of S8 to StS and copolymerization time were synthesized. Various spectroscopic methods (1H NMR, 13C NMR, Raman spectroscopy and FTIR spectroscopy) were applied to characterize the chemical structure of the copolymers. Additionally, the phase structure and thermal stability of the synthesized polysulfides were investigated using DSC and TGA, respectively. The successful anionic copolymerization of styrene sulfide and elemental sulfur has been demonstrated. Full article
(This article belongs to the Special Issue Current Problems of the Organic Chemistry of Sulfur and Selenium)
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12 pages, 5387 KiB  
Article
Bioselectivity Induced by Chirality of New Terpenyl Organoselenium Compounds
by Magdalena Obieziurska, Agata J. Pacuła, Angelika Długosz-Pokorska, Marek Krzemiński, Anna Janecka and Jacek Ścianowski
Materials 2019, 12(21), 3579; https://doi.org/10.3390/ma12213579 - 31 Oct 2019
Cited by 17 | Viewed by 2323
Abstract
A series of new chiral benzisoselenazol-3(2H)-ones substituted on the nitrogen atom with three monoterpene moieties—p-menthane, pinane and carane—was synthesized. The compounds were obtained by the reaction of 2-(chloroseleno)benzoyl chloride with an appropriate terpene amine, first synthesized by a multistep methodology starting [...] Read more.
A series of new chiral benzisoselenazol-3(2H)-ones substituted on the nitrogen atom with three monoterpene moieties—p-menthane, pinane and carane—was synthesized. The compounds were obtained by the reaction of 2-(chloroseleno)benzoyl chloride with an appropriate terpene amine, first synthesized by a multistep methodology starting from the corresponding alcohol (p-menthane system) or alkene (pinene and carene systems). Compounds were tested as antioxidants and anticancer agents. The N-isopinocampheyl-1,2-benzisoselenazol-3(2H)-one was the best peroxide scavenger and antiproliferative agent on the human promyelocytic leukemia cell line HL-60. The N-menthyl-1,2-benzisoselenazol-3(2H)-one revealed the highest anticancer potential towards breast cancer line MCF-7. The influence of structure and chirality on the bio-activity of the obtained organoselenium compounds was thoroughly evaluated. Full article
(This article belongs to the Special Issue Current Problems of the Organic Chemistry of Sulfur and Selenium)
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18 pages, 4320 KiB  
Article
Diferrocenyl Thioketone: Reactions with (Bisphosphane)Pt(0) Complexes—Electrochemical and Computational Studies
by Sebastian Gröber, Piotr Matczak, Sławomir Domagała, Thomas Weisheit, Helmar Görls, Annika Düver, Grzegorz Mlostoń and Wolfgang Weigand
Materials 2019, 12(17), 2832; https://doi.org/10.3390/ma12172832 - 03 Sep 2019
Cited by 4 | Viewed by 2925
Abstract
Diferrocenyl thioketone reacts smoothly with (bisphosphane)Pt(0) complexes in toluene solution at room temperature yielding 1:1 adducts identified as ferrocenyl (Fc) functionalized platinathiiranes. Their structures were unambiguously confirmed by means of spectroscopic methods as well as by X-ray diffraction analysis. A unique, ferrocene-rich platinathiirane, [...] Read more.
Diferrocenyl thioketone reacts smoothly with (bisphosphane)Pt(0) complexes in toluene solution at room temperature yielding 1:1 adducts identified as ferrocenyl (Fc) functionalized platinathiiranes. Their structures were unambiguously confirmed by means of spectroscopic methods as well as by X-ray diffraction analysis. A unique, ferrocene-rich platinathiirane, bearing three Fc-units, was prepared starting with [bis(diphenylphosphino)ferrocene] Pt(0(η2-norbornene). For comparison, a similar platinathiirane with one Fc-unit was obtained from the reaction of the latter complex with thiobenzophenone. Quantum-chemical calculations were carried out to describe the bonding pattern and frontier molecular orbitals of the ferrocene-rich platinathiirane complexes. These calculations confirmed that the C=S bond loses its formally double-bond character upon complexation (bisphosphane)Pt(0). Cyclic voltammetry measurements were performed to characterize the obtained platinathiiranes in CH2Cl2 solutions. For comparison, the cyclic voltammogram for diferrocenyl thioketoneas a mixed-valent (FeII-FeIII) compound was also recorded and analyzed. The results point out to a diffusion controlled electrode process in case of differocenyl thioketone and mixed diffusion and adsorption controlled electrode process in the case of the studied platinathiiranes. Full article
(This article belongs to the Special Issue Current Problems of the Organic Chemistry of Sulfur and Selenium)
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26 pages, 9731 KiB  
Article
The Effect of New Thiophene-Derived Diphenyl Aminophosphonates on Growth of Terrestrial Plants
by Diana Rogacz, Jarosław Lewkowski, Marta Siedlarek, Rafał Karpowicz, Anna Kowalczyk and Piotr Rychter
Materials 2019, 12(12), 2018; https://doi.org/10.3390/ma12122018 - 24 Jun 2019
Cited by 2 | Viewed by 2546
Abstract
The aim of this work was to evaluate the impact of the thiophene-derived aminophosphonates 1–6 on seedling emergence and growth of monocotyledonous oat (Avena sativa) and dicotyledonous radish (Raphanus sativus L.), and phytotoxicity against three persistent and resistant [...] Read more.
The aim of this work was to evaluate the impact of the thiophene-derived aminophosphonates 1–6 on seedling emergence and growth of monocotyledonous oat (Avena sativa) and dicotyledonous radish (Raphanus sativus L.), and phytotoxicity against three persistent and resistant weeds (Galinsoga parviflora Cav., Rumex acetosa L., and Chenopodium album). Aminophosphonates 1–6 have never been described in the literature. The phytotoxicity of tested aminophosphonates toward their potential application as soil-applied herbicides was evaluated according to the OECD (Organization for Economic and Cooperation Development Publishing) 208 Guideline. In addition, their ecotoxicological impact on crustaceans Heterocypris incongruens and bacteria Aliivibrio fischeri was measured using the OSTRACODTOXKITTM and Microtox® tests. Obtained results showed that none of the tested compounds were found sufficiently phytotoxic and none of them have any herbicidal potential. None of the tested compounds showed important toxicity against Aliivibrio fischeri but they should be considered as slightly harmful. Harmful impacts of compounds 1–6 on Heterocypris incongruens were found to be significant. Full article
(This article belongs to the Special Issue Current Problems of the Organic Chemistry of Sulfur and Selenium)
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Review

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22 pages, 37780 KiB  
Review
The hetero-Friedel-Crafts-Bradsher Cyclizations with Formation of Ring Carbon-Heteroatom (P, S) Bonds, Leading to Organic Functional Materials
by Joanna Skalik, Marek Koprowski, Ewa Różycka-Sokołowska and Piotr Bałczewski
Materials 2020, 13(21), 4751; https://doi.org/10.3390/ma13214751 - 23 Oct 2020
Cited by 1 | Viewed by 2643
Abstract
The interest in functional materials possessing improved properties led to development of new methods of their synthesis, which allowed to obtain new molecular arrangements with carbon and heteroatom motifs. Two of the classical reactions of versatile use are the Friedel-Crafts and the Bradsher [...] Read more.
The interest in functional materials possessing improved properties led to development of new methods of their synthesis, which allowed to obtain new molecular arrangements with carbon and heteroatom motifs. Two of the classical reactions of versatile use are the Friedel-Crafts and the Bradsher reactions, which in the new heteroatomic versions allow to replace ring carbon atoms by heteroatoms. In the present work, we review methods of synthesis of C–S and C–P bonds utilizing thia- and phospha-Friedel-Crafts-Bradsher cyclizations. Single examples of C–As and lack of C–Se bond formation, involving two of the closest neighbors of P and S in the periodic table, have also been noted. Applications of the obtained π-conjugated molecules, mainly as semiconducting materials, flame retardants, and resins hardeners, designed on the basis of five- and six-membered cyclic molecules containing ring phosphorus and sulfur atoms, are also included. This comprehensive review covers literature up to August 2020. Full article
(This article belongs to the Special Issue Current Problems of the Organic Chemistry of Sulfur and Selenium)
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