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Organosulfur and Organoselenium Chemistry
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Organosulfur and Organoselenium Chemistry

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

Deadline for manuscript submissions: 31 July 2024 | Viewed by 4631

Special Issue Editor

Prof. Dr. Ming Wang

E-Mail Website
Guest Editor
School of Chemistry and Molecular Engineering, East China Normal University, 3663, Shanghai 200062, China
Interests: organic chemistry; organic synthesis methodology; organosulfur chemistry; asymmetric catalysis

Special Issue Information

Dear Colleagues,

Sulfur- and selenium-containing compounds are important in organic synthesis. These sulfur- and selenium-containing molecules are not only widely applied in pharmaceuticals, materials, natural products, biology, etc., but they are also useful building blocks in organic synthesis. Additionally, sulfur and selenium show divergent functions and potencies in different oxidative states, which has led to the rich chemistry of sulfur and selenium in organic synthesis. The diversified oxidation states enable sulfur and selenium to acquire significant functions for pharmacokinetics and pharmacodynamics in the development of pharmaceuticals. The unique optical and electronic properties of sulfur and selenium also make this element indispensable in organic photoconducting materials and batteries.

Molecules plans to publish a Special Issue comprising high-quality contributions by top researchers in the field of organosulfur and organoselenium chemistry. This Special Issue invites original papers and reviews reporting on recent progress in the development of novel organosulfur and organoselenium chemistry. In this Special Issue, we hope to offer insights into different research areas of organosulfur and organoselenium chemistry by active researchers in the relevant field. The topics include the synthesis and transformation of sulfur- and selenium-containing compounds, and their application in polymer, organic semiconductors, pharmaceuticals, and the agrochemical and food chemistry.

Dr. Ming Wang
Guest Editor

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. Molecules 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 2700 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

  • organosulfur
  • organoselenium
  • synthesis
  • transformation
  • application

Published Papers (4 papers)

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Research

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18 pages, 2520 KiB  
Article
Upper Rim-Bridged Calix[4]arenes via Cyclization of meta Alkynyl Intermediates with Diphenyl Diselenide
by Anastasia Surina, Karolína Salvadori, Matěj Poupě, Jan Čejka, Ludmila Šimková and Pavel Lhoták
Molecules 2024, 29(6), 1237; https://doi.org/10.3390/molecules29061237 - 11 Mar 2024
Viewed by 721
Abstract
A Sonogashira coupling of meta-iodocalix[4]arene with various terminal acetylenes confirmed that the meta position of calixarene is well addressable, and that both thermal and microwave protocols led to good yields of alkynylcalixarenes. Alkynes thus obtained were subjected to the ferric chloride and [...] Read more.
A Sonogashira coupling of meta-iodocalix[4]arene with various terminal acetylenes confirmed that the meta position of calixarene is well addressable, and that both thermal and microwave protocols led to good yields of alkynylcalixarenes. Alkynes thus obtained were subjected to the ferric chloride and diphenyl diselenide-promoted electrophilic closure. It turns out that the calix[4]arenes give completely different bridging products than those described for the non-macrocyclic starting compounds. This can be demonstrated not only by the isolation of products with a six-membered ring (6-exo-dig), but mainly by the smooth formation of the 5-endo-dig cyclization, which has never been observed in the aliphatic series. An attempt at electrocyclization led to a high yield of the 1,2-diketone (oxidation of the starting alkyne), again in contrast to the reaction described for the acyclic derivatives. The structures of the unexpected products were unequivocally established by X-ray analysis and clearly demonstrate how the preorganized macrocyclic skeleton favors a completely different regioselectivity of cyclization reactions compared to common aliphatic compounds. Full article
(This article belongs to the Special Issue Organosulfur and Organoselenium Chemistry)
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13 pages, 1000 KiB  
Article
Selenium Biofortification Effect on Glucosinolate Content of Brassica oleracea var. italic and Eruca vesicaria
by Azra Đulović, Katarina Usanović, Lea Kukoč Modun and Ivica Blažević
Molecules 2023, 28(20), 7203; https://doi.org/10.3390/molecules28207203 - 21 Oct 2023
Cited by 2 | Viewed by 915
Abstract
Glucosinolates (GSLs) in different plant parts of broccoli (Brassica oleracea var. italic) and rocket (Eruca vesicaria) were analyzed qualitatively and quantitatively before and after treatment with sodium selenate (2 and 5 mM), by their desulfo-counterparts using the UHPLC-DAD-MS/MS technique. [...] Read more.
Glucosinolates (GSLs) in different plant parts of broccoli (Brassica oleracea var. italic) and rocket (Eruca vesicaria) were analyzed qualitatively and quantitatively before and after treatment with sodium selenate (2 and 5 mM), by their desulfo-counterparts using the UHPLC-DAD-MS/MS technique. Twelve GSLs were detected in broccoli (five aliphatic, one arylaliphatic, and six indolic), where 4-(methylsulfanyl)butyl GSL (glucoerucin) was the main one in the roots (4.88–9.89 µmol/g DW), 4-(methylsulfinyl)butyl GSL (glucoraphanin) in stems (0.44–1.11 µmol/g DW), and 4-hydroxyindol-3-ylmethyl GSL (4-hydroxyglucobrassicin) in leaves (0.51–0.60 µmol/g DW). No GSL containing selenium was detected in the treated broccoli. Ten GSLs were detected in rocket (seven aliphatic and three indolic), where 4-(methylsulfanyl)butyl GSL (glucoerucin) was the main one in the roots (4.50–20.59 µmol/g DW) and 4-methoxyindol-3-ylmethyl GSL (4-methoxyglucobrassicin) in the aerial part (0.57–5.69 µmol/g DW). As a result of induced stress by selenium fertilization, the total GSL content generally increased in both plants. In contrast to broccoli, the roots and the aerial part of the rocket treated with a high concentration of sodium selenate contained 4-(methylseleno)butyl GSL (glucoselenoerucin) (0.36–4.48 µmol/g DW). Although methionine-derived GSLs are the most abundant in both plants, the plants’ ability to tolerate selenate and its regulation by selenoglucosinolate production is species- and growth-stage-dependent. Full article
(This article belongs to the Special Issue Organosulfur and Organoselenium Chemistry)
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Review

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19 pages, 10172 KiB  
Review
Synthesis of Thionated Perylenediimides: State of the Art and First Investigations of an Alternative to Lawesson’s Reagent
by Oksana Kharchenko, Anna Hryniuk, Oksana Krupka and Piétrick Hudhomme
Molecules 2024, 29(11), 2538; https://doi.org/10.3390/molecules29112538 - 28 May 2024
Viewed by 247
Abstract
Perylenediimides (PDIs) are composed of a central perylene ring, on which are grafted two imide groups at the peri positions. Thionated PDIs are characterized by the substitution of one or more oxygen atoms of these imide functions with sulfur atoms. This structural modification [...] Read more.
Perylenediimides (PDIs) are composed of a central perylene ring, on which are grafted two imide groups at the peri positions. Thionated PDIs are characterized by the substitution of one or more oxygen atoms of these imide functions with sulfur atoms. This structural modification alters the electronic properties with a redshift of the optical absorption accompanied by modification of the charge transport characteristics compared to their non-thionated counterparts. These properties make them suitable candidates for applications in optoelectronic devices, such as organic light-emitting diodes and organic photovoltaics. Moreover, the presence of sulfur atom(s) can favor the promotion of reactive oxygen species production for photodynamic and photothermal therapies. These thionated PDIs can be synthesized through the post-functionalization of PDIs by using a sulfurizing reagent. Nevertheless, the main drawbacks remain the difficulties in adjusting the degree of thionation and obtaining tri- and tetrathionated PDIs. Up to now, this thionation reaction has been described almost exclusively using Lawesson’s reagent. In the current study, we present our first investigations into an alternative reagent to enhance selectivity and achieve a greater degree of thionation. The association of phosphorus pentasulfide with hexamethyldisiloxane (Curphey’s reagent) clearly demonstrated higher reactivity compared with Lawesson’s reagent to attain multi-thionated PDIs. Full article
(This article belongs to the Special Issue Organosulfur and Organoselenium Chemistry)
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28 pages, 11924 KiB  
Review
Towards More Practical Methods for the Chemical Synthesis of Thioamides Using Sulfuration Agents: A Decade Update
by Qiang Zhang, Laurent Soulère and Yves Queneau
Molecules 2023, 28(8), 3527; https://doi.org/10.3390/molecules28083527 - 17 Apr 2023
Cited by 3 | Viewed by 2241
Abstract
Compounds possessing a thioamide function play a crucial role in organic synthesis, serving as key building blocks. They are also important in the pharmaceutical chemistry and drug design, owing to their ability to mimic the amide function in biomolecules while retaining or developing [...] Read more.
Compounds possessing a thioamide function play a crucial role in organic synthesis, serving as key building blocks. They are also important in the pharmaceutical chemistry and drug design, owing to their ability to mimic the amide function in biomolecules while retaining or developing biological activity. From the synthetic viewpoint, several methods have been developed for preparing thioamides using sulfuration agents. The purpose of this review is to give an update of the last decade of contributions focusing on the formation of thioamides employing different sulfur sources. When appropriate, the cleanness and practicality of the new methods are highlighted. Full article
(This article belongs to the Special Issue Organosulfur and Organoselenium Chemistry)
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