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Advances in Modern Fluorine Chemistry
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Advances in Modern Fluorine Chemistry

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

Deadline for manuscript submissions: closed (31 December 2023) | Viewed by 6305

Special Issue Editors

Dr. Yee Hwee Lim

E-Mail Website
Guest Editor
Green Chemistry and Biocatalysis, Institute of Sustainability for Chemicals, Energy and Environment, Singapore, Singapore
Interests: biocatalytic fluorination; halogenation and synthetic methodologies
Dr. Justyna Walkowiak-Kulikowska

E-Mail Website
Guest Editor
Faculty of Chemistry, Adam Mickiewicz University in Poznan, Poznań, Poland
Interests: synthesis, characterization, modification and application of fluorinated polymers & materials

Special Issue Information

Dear Colleague,

Scientific advancement and modern chemical technologies have led to deeper understanding of how fluorine in molecules affects their structure, reactivity, and function. It is well-understood today that fluorine’s electronegativity and small size can significantly improve the physical and chemical properties of the molecules. As a result, fluorination is widely employed in the preparation of pharmaceutical drugs, agrochemicals, materials, polymers, and catalysts to optimize structure and properties. Beyond this, the short-lived radioisotope of fluorine, fluorine-18, has also been exploited in medical Positron Emission Tomography (PET) imaging. As such, numerous fluorination methodologies, reagents, and catalysts have continued to be invented and developed to install fluorine in precise location of the molecule and in a safer or greener and more sustainable manner. Although fluorinated molecules or materials are largely man-made, nature does produce fluorinated natural compounds, albeit in only a handful number. Understanding of fluorine biosynthesis continues to fascinate researchers as we hope to better harness Nature’s mechanism to make fluorinated molecules under benign conditions. Lastly, even though fluorine has many positive impacts on our lives, the study and understanding of the effect of fluorine or its removal from the environment cannot be overlooked.

In this Special Issue of “Advances in Modern Fluorine Chemistry”, we aim to bring together scholarly articles and contributions on the latest advances and development in the field of modern fluorine chemistry. Diverse aspects of fluorine chemistry, fluorine, perfluorinated or fluorous materials, or polymers, including methodologies, reagents, applications, safety, analysis, and environmental impact, are all welcome and accepted. This Special Issue accepts contributions as full papers, communications, perspectives, and reviews.

Dr. Yee Hwee Lim
Dr. Justyna Walkowiak-Kulikowska
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. 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

  • fluorination methodologies
  • fluorinated polymers or materials
  • fluorinated molecules synthesis and application
  • fluorine biosynthesis
  • radiofluorination
  • fluorinated drugs
  • fluorine reagents
  • fluorine analysis

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Published Papers (5 papers)

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Research

16 pages, 6474 KiB  
Article
1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me3SiCF2H/Me3SiCF3 Facilitated by CsF/18-Crown-6
by Dingben Chen, Ling Huang, Mingyu Liang, Xiaojing Chen, Dongdong Cao, Pan Xiao, Chuanfa Ni and Jinbo Hu
Molecules 2024, 29(12), 2905; https://doi.org/10.3390/molecules29122905 - 19 Jun 2024
Viewed by 708
Abstract
The direct 1,6-nucleophilic difluoromethylation, trifluoromethylation, and difluoroalkylation of para-quinone methides (p-QMs) with Me3SiRf (Rf = CF2H, CF3, CF2CF3, CF2COOEt, and CF2SPh) under mild conditions are described. [...] Read more.
The direct 1,6-nucleophilic difluoromethylation, trifluoromethylation, and difluoroalkylation of para-quinone methides (p-QMs) with Me3SiRf (Rf = CF2H, CF3, CF2CF3, CF2COOEt, and CF2SPh) under mild conditions are described. Although Me3SiCF2H shows lower reactivity than Me3SiCF3, it can react with p-QMs promoted by CsF/18-Crown-6 to give structurally diverse difluoromethyl products in good yields. The products can then be further converted into fluoroalkylated para-quinone methides and α-fluoroalkylated diarylmethanes. Full article
(This article belongs to the Special Issue Advances in Modern Fluorine Chemistry)
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10 pages, 3205 KiB  
Article
Synthesis of Calamitic Fluorinated Mesogens with Complex Crystallization Behavior
by Denis Anokhin, Alina Maryasevskaya, Ainur Abukaev, Umut Ugur Ozkose, Alexander Buglakov, Dimitri A. Ivanov and Bruno Améduri
Molecules 2023, 28(24), 8002; https://doi.org/10.3390/molecules28248002 - 8 Dec 2023
Viewed by 1334
Abstract
This work presents the synthesis and self-organization of the calamitic fluorinated mesogen, 1,1,2,2–tetrafluoro–2–(1,1,2,2–tetrafluoro–4–iodobutoxy)ethanesulfonic acid, a potential model for perfluorosulfonic acid membranes (PFSA). The compound is derived in three steps from 1,1,2,2–tetrafluoro–2–(1,1,2,2–tetrafluoro–2–iodoethoxy)ethanesulfonyl fluoride, achieving a 78% overall yield. The resulting compound exhibits intricate thermal [...] Read more.
This work presents the synthesis and self-organization of the calamitic fluorinated mesogen, 1,1,2,2–tetrafluoro–2–(1,1,2,2–tetrafluoro–4–iodobutoxy)ethanesulfonic acid, a potential model for perfluorosulfonic acid membranes (PFSA). The compound is derived in three steps from 1,1,2,2–tetrafluoro–2–(1,1,2,2–tetrafluoro–2–iodoethoxy)ethanesulfonyl fluoride, achieving a 78% overall yield. The resulting compound exhibits intricate thermal behavior. At 150 °C, a crystal-to-crystal transition is observed due to the partial disordering of calamitic molecules, which is followed by isotropization at 218 °C. Upon cooling, sample ordering occurs through the formation of large smectic liquid crystalline phase domains. This thermotropic state transforms into a layered crystal phase at lower temperatures, characterized by alternating hydrophilic and hydrophobic layers. Using X-ray diffraction, crystalline unit cell models at both room temperature and 170 °C were proposed. Computer simulations of the molecule across varying temperatures support the idea that thermal transitions correlate with a loss of molecular orientation. Importantly, the study underscores the pivotal role of precursor self-organization in aligning channels during membrane fabrication, ensuring controlled and oriented positioning. Full article
(This article belongs to the Special Issue Advances in Modern Fluorine Chemistry)
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11 pages, 2753 KiB  
Article
Poly Caprolactam Supported Hexaethylene Glycolic Imidazolium Ionic Liquid as a Heterogeneous Promoter for Nucleophilic Fluorination
by Mudumala Veeranarayana Reddy, Keun Heok Park and Dong Wook Kim
Molecules 2023, 28(18), 6747; https://doi.org/10.3390/molecules28186747 - 21 Sep 2023
Viewed by 1096
Abstract
Hexaethylene glycolic vinyl imidazolium (hexaEGVIM) was supported on N-vinyl caprolactam via covalent bonds through simple copolymerization to form poly caprolactam-supported hexaethylene glycol-substituted imidazolium salts (PCLS-hexaEGIM). The resulting heterogeneous PCLS-hexaEGIM promoter was active, selective, and stable for aliphatic nucleophilic substitution reactions using alkali [...] Read more.
Hexaethylene glycolic vinyl imidazolium (hexaEGVIM) was supported on N-vinyl caprolactam via covalent bonds through simple copolymerization to form poly caprolactam-supported hexaethylene glycol-substituted imidazolium salts (PCLS-hexaEGIM). The resulting heterogeneous PCLS-hexaEGIM promoter was active, selective, and stable for aliphatic nucleophilic substitution reactions using alkali metal salts. The alkali metal salts dramatically enhanced the reactivity of this heterogeneous catalyst with easily isolable higher product yields, reducing the formation of by-products. Therefore, nucleophilic fluorination and other substitution reactions can act as highly efficient catalysts in various sulfonyloxyalkanes and haloalkanes with regard to their corresponding fluorinated products. Full article
(This article belongs to the Special Issue Advances in Modern Fluorine Chemistry)
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10 pages, 1640 KiB  
Article
Activation of SF5CF3 by the N-Heterocyclic Carbene SIMes
by Domenique Herbstritt, Pooja Tomar and Thomas Braun
Molecules 2023, 28(18), 6693; https://doi.org/10.3390/molecules28186693 - 19 Sep 2023
Viewed by 1099
Abstract
The greenhouse gas SF5CF3 was photochemically activated with SIMes (1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene) to give 1,3-dimesityl-2,2-difluoroimidazolidine (SIMesF2), and 1,3-dimesitylimidazolidine-2-sulfide, as well as the trifluoromethylated carbene derivative 1,3-dimesityl-2-fluoro-2-trifluoromethylimidazolidine. CF3 radicals, as well as SF4, serve presumably as intermediates of [...] Read more.
The greenhouse gas SF5CF3 was photochemically activated with SIMes (1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene) to give 1,3-dimesityl-2,2-difluoroimidazolidine (SIMesF2), and 1,3-dimesitylimidazolidine-2-sulfide, as well as the trifluoromethylated carbene derivative 1,3-dimesityl-2-fluoro-2-trifluoromethylimidazolidine. CF3 radicals, as well as SF4, serve presumably as intermediates of the conversions. In addition, the photochemical activation of SF5CF3 was performed in the presence of triphenylphosphine. The formation of triphenyldifluorophosphorane and triphenylphosphine sulfide was observed. Full article
(This article belongs to the Special Issue Advances in Modern Fluorine Chemistry)
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31 pages, 5091 KiB  
Article
Access to 2-Fluorinated Aziridine-2-phosphonates from α,α-Halofluorinated β-Iminophosphonates—Spectroscopic and Theoretical Studies
by Mateusz Klarek, Tomasz Siodła, Tahar Ayad, David Virieux and Magdalena Rapp
Molecules 2023, 28(14), 5579; https://doi.org/10.3390/molecules28145579 - 22 Jul 2023
Cited by 1 | Viewed by 1467
Abstract
The efficient one-pot halofluorination of a β-enaminophosphonate/β-iminophosphonate tautomeric mixture resulting in α,α-halofluorinated β-iminophosphonates is reported. Subsequent imine reduction gave the corresponding β-aminophosphonates as a racemic mixture or with high diastereoselectivity. The proposed protocol is the [...] Read more.
The efficient one-pot halofluorination of a β-enaminophosphonate/β-iminophosphonate tautomeric mixture resulting in α,α-halofluorinated β-iminophosphonates is reported. Subsequent imine reduction gave the corresponding β-aminophosphonates as a racemic mixture or with high diastereoselectivity. The proposed protocol is the first example of a synthesis of N-inactivated aziridines substituted by a fluorine and phosphonate moiety on the same carbon atom. Based on spectroscopic and theoretical studies, we determined the cis/trans geometry of the resulting fluorinated aziridine-2-phosphonate. Our procedure, involving the reduction of cis/trans-fluoroaziridine mixture 24, allows us to isolate chiral trans-aziridines 24 as well as cis-aziridines 27 that do not contain a fluorine atom. We also investigated the influence of the fluorine atom on the reactivity of aziridine through an acid-catalyzed regioselective ring-opening reaction. The results of DFT calculations, at the PCM/ωB97x-D/def2-TZVPD level of theory, are in good agreement with the experiments. The transition states of the SN2 intramolecular cyclization of vicinal haloamines have been modeled. Full article
(This article belongs to the Special Issue Advances in Modern Fluorine Chemistry)
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