Special Issue "Organo-Fluorine Chemical Science"

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A special issue of Applied Sciences (ISSN 2076-3417). This special issue belongs to the section "Applied Chemistry".

Deadline for manuscript submissions: closed (15 October 2015)

Special Issue Editor

Guest Editor
Dr. Helmut Martin Hügel

School of Applied Sciences (Chemistry), RMIT University, Melbourne VIC 3001, PO Box 2476V, Australia
E-Mail
Phone: +61 399252626
Fax: +61 3 99253747
Interests: clinical and medicinal chemistry; chinese herbal medicine; chemical synthesis of natural and bioactive products; greener chemistry; sustainable chemistry; fragrance chemistry; microwave chemistry

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Marine

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Image credit to: EMSL
(ISBN 3-906980-33-2)

Special Issue
Organo-Fluorine Chemical Science
Inventing the Fluorine Future
2012
Helmut Martin Hügel (Ed.)
ISBN 3-906980-33-2

Dear Colleagues,

The unique properties imparted on molecules by fluorine substitution, continues to be the subject of intense research as the products have widespread application in all areas of science. Incorporation of fluorine can productively and unpredictably modulate several properties that interest medicinal chemists. Selected drugs for the treatment of high cholesterol such as LipitorⓇ by Pfizer, CrestorⓇ by AstraZeneca, ZetiaⓇ by Merck/Schering-Plough and LescolⓇ by Novartis all of which contain one or more fluorine atoms that increase metabolic stability, rank amongst the highest selling prescription drugs ever developed. Without doubt every current drug discovery and development program includes and evaluates fluorine-containing drug candidates. A one step 18F-labeling of peptides that contain a specific arene group has emerged that is rapid and simple to perform for 18F PET (positron emission tomography) an in vivo imaging technology for medical use has potential wide application. The synthesis of many pharmaceuticals and agrochemicals with fluorine atoms or groups is closely dependent on the development of new chemical methodologies by organic and industrial chemists. Monofluoroalkenes are known as nonisomerable, nonhydrolyzable stable bioisosteres of amide bonds and recently published highly enantio- and diastereoselective organocatalytic monofluorovinylations reactions have led to the isolation of monofluorovinylated products. A practical methodology for the enatioselective a-fluorination of ketene enolates has been optimized by the utilization of a three-component catalysis system provides an array of a-fluorocarboxylic acid derivatives. A generally useful coupling protocol for copper-catalyzed 1H-perfluoroalkane arylation by aryl iodides allows ready access to a range of perfluoroalkyl substituted aromatic compounds. Tetrafluoroethylene (TFE) is the organofluorine feedstock for the production of poly-(tetrafluoroethylene)polymers that have many applications. The transformation of TFE to a,b,b,-trifluorostyrenes via palladium-catalyzed coupling and arylzincs has been achieved in excellent yields and paves the way to new fluorine-polymers. The deployment of a fluorine substituted conjugated polymer in photovoltaic cells exhibited medium band gap yields above 7% attributed in part to the increased hole mobility of the fluorinated polymer. Organo-fluorine chemistry has had an enormous global impact on science and society, the fluorine fever continues to flourish and grow and we are delighted that experts in this field have agreed to contribute their research achievements to this special issue.

Dr. Helmut Martin Hügel
Guest Editor

Keywords

  • fluorinated drugs
  • fluorine-medicinal chemistry
  • perfluorinated heterocycles
  • fluorous mixture synthesis
  • fluorine-chemical biology
  • fluorine-chemistry
  • fluorine-toxicology
  • fluorine-industry
  • fluorine-products

Published Papers (19 papers)

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Editorial

Jump to: Research, Review

Open AccessEditorial Special Feature Organo-Fluorine Chemical Science
Appl. Sci. 2012, 2(2), 558-565; doi:10.3390/app2020558
Received: 25 May 2012 / Accepted: 25 May 2012 / Published: 4 June 2012
Cited by 10 | PDF Full-text (203 KB) | HTML Full-text | XML Full-text
Abstract
Fluorine is the 13th most abundant element and, with other fluorine containing functional groups, is a most effective element in biological substances, pharmaceuticals, agrochemicals, liquid crystals, dyes, polymers and a wide range of consumer products. This reflects its resistance to metabolic change due
[...] Read more.
Fluorine is the 13th most abundant element and, with other fluorine containing functional groups, is a most effective element in biological substances, pharmaceuticals, agrochemicals, liquid crystals, dyes, polymers and a wide range of consumer products. This reflects its resistance to metabolic change due to the strength of the C-F bond providing biological stability and the application of its nonstick-interfacial physical characteristics. Its introduction often remains a synthetic challenge. The widespread use of organofluorines has increased the demand for the development of practical and simple reagents and experimental strategies for the incorporation of fluorine into all types of molecular structures and this was the reasoning behind this special feature on Organo-Fluorine Chemical Science.The contributed articles belong to two broad groups: (i) preparation of fluorine materials, polymers; (ii) the synthesis/applications of organo-fluorine molecules. [...] Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)

Research

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Open AccessArticle Improved Permeate Flux of PVDF Ultrafiltration Membrane Containing PVDF-g-PHEA Synthesized via ATRP
Appl. Sci. 2015, 5(4), 1992-2008; doi:10.3390/app5041992
Received: 10 September 2015 / Revised: 8 December 2015 / Accepted: 14 December 2015 / Published: 21 December 2015
PDF Full-text (2487 KB) | HTML Full-text | XML Full-text
Abstract
Polyvinylidene fluoride (PVDF) ultrafiltration (UF) membrane combined with polyvinylidene fluoride-graft-2-hydroxyethyl acrylate (PVDF-g-PHEA) was fabricated via non-solvent induced phase separation (NIPS). In this study, PVDF-g-PHEA was synthesized via atom transfer radical polymerization (ATRP) method, and then synthesized graft copolymer was characterized using Fourier transform
[...] Read more.
Polyvinylidene fluoride (PVDF) ultrafiltration (UF) membrane combined with polyvinylidene fluoride-graft-2-hydroxyethyl acrylate (PVDF-g-PHEA) was fabricated via non-solvent induced phase separation (NIPS). In this study, PVDF-g-PHEA was synthesized via atom transfer radical polymerization (ATRP) method, and then synthesized graft copolymer was characterized using Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR) and thermogravimetry analysis (TGA). Moreover, PVDF membranes containing graft copolymer (PVDF-g-PHEA) showed lower water contact angle value than pristine PVDF membranes. Macrovoid holes were also observed in cross sectional scanning electron microscope (SEM) image of PVDF membrane containing PVDF-g-PHEA. Accordingly, it was confirmed that these characteristics led PVDF membrane blended with graft copolymer has high final permeate flux and normalized flux compared to pristine PVDF membrane. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
Open AccessArticle Fluorine Based Superhydrophobic Coatings
Appl. Sci. 2012, 2(2), 453-464; doi:10.3390/app2020453
Received: 15 February 2012 / Revised: 24 April 2012 / Accepted: 2 May 2012 / Published: 8 May 2012
Cited by 36 | PDF Full-text (725 KB) | HTML Full-text | XML Full-text
Abstract
Superhydrophobic coatings, inspired by nature, are an emerging technology. These water repellent coatings can be used as solutions for corrosion, biofouling and even water and air drag reduction applications. In this work, synthesis of monodispersive silica nanoparticles of ~120 nm diameter has been
[...] Read more.
Superhydrophobic coatings, inspired by nature, are an emerging technology. These water repellent coatings can be used as solutions for corrosion, biofouling and even water and air drag reduction applications. In this work, synthesis of monodispersive silica nanoparticles of ~120 nm diameter has been realized via Stöber process and further functionalized using fluoroalkylsilane (FAS-17) molecules to incorporate the fluorinated groups with the silica nanoparticles in an ethanolic solution. The synthesized fluorinated silica nanoparticles have been spin coated on flat aluminum alloy, silicon and glass substrates. Functionalization of silica nanoparticles with fluorinated groups has been confirmed by Fourier Transform Infrared spectroscopy (FTIR) by showing the presence of C-F and Si-O-Si bonds. The water contact angles and surface roughness increase with the number of spin-coated thin films layers. The critical size of ~119 nm renders aluminum surface superhydrophobic with three layers of coating using as-prepared nanoparticle suspended solution. On the other hand, seven layers are required for a 50 vol.% diluted solution to achieve superhydrophobicity. In both the cases, water contact angles were more than 150°, contact angle hysteresis was less than 2° having a critical roughness value of ~0.700 µm. The fluorinated silica nanoparticle coated surfaces are also transparent and can be used as paint additives to obtain transparent coatings. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
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Open AccessArticle Further Successes of the Meisenheimer Model
Appl. Sci. 2012, 2(2), 443-452; doi:10.3390/app2020443
Received: 5 April 2012 / Revised: 27 April 2012 / Accepted: 27 April 2012 / Published: 4 May 2012
Cited by 2 | PDF Full-text (300 KB) | HTML Full-text | XML Full-text
Abstract
Our simple Meisenheimer model for predicting the principal site for nucleophilic substitution in aromatic perfluorocarbons is further tested on a series of recently published reactions in liquid ammonia primarily from Malykhin and coworkers. The model accurately predicts the experimental results for all of
[...] Read more.
Our simple Meisenheimer model for predicting the principal site for nucleophilic substitution in aromatic perfluorocarbons is further tested on a series of recently published reactions in liquid ammonia primarily from Malykhin and coworkers. The model accurately predicts the experimental results for all of the reactions reported further confirming its general applicability. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
Open AccessArticle Synthesis of Some New Fluorinated Hexahydroquinoline and Acridinedione Derivatives in Trifluoroethanol
Appl. Sci. 2012, 2(2), 368-374; doi:10.3390/app2020368
Received: 29 January 2012 / Revised: 6 April 2012 / Accepted: 9 April 2012 / Published: 18 April 2012
Cited by 4 | PDF Full-text (248 KB) | HTML Full-text | XML Full-text
Abstract This article describes one-pot synthesis of new fluorinated hexahydroquinoline derivatives via unsymmetric Hantzsch reaction involving 5-trifluoromethyl-1,3-cyclohexanedione, aldehydes, acetoacetate ester, and ammonium acetate in trifluoroethanol (TFE). The reaction is simple and rapid with high yield. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
Open AccessArticle Application of Liquid-Phase Direct Fluorination: Novel Synthetic Methods for a Polyfluorinated Coating Material and a Monomer of a Perfluorinated Polymer Electrolyte Membrane
Appl. Sci. 2012, 2(2), 327-341; doi:10.3390/app2020327
Received: 13 March 2012 / Revised: 22 March 2012 / Accepted: 26 March 2012 / Published: 10 April 2012
Cited by 2 | PDF Full-text (294 KB) | HTML Full-text | XML Full-text
Abstract
A new polyfluorinated anti-staining coating material CF3O(CF2CF2O)xCF2-CONHCH2CH2CH2Si(OCH3)3 has been developed by utilizing the PERFECT method, which employs a liquid-phase direct fluorination reaction with elemental
[...] Read more.
A new polyfluorinated anti-staining coating material CF3O(CF2CF2O)xCF2-CONHCH2CH2CH2Si(OCH3)3 has been developed by utilizing the PERFECT method, which employs a liquid-phase direct fluorination reaction with elemental fluorine as a key step. Direct fluorination of a partially-fluorinated ester, which was prepared from a non-fluorinated poly(ethylene glycol) and a perfluorinated acyl fluoride, followed by methanolysis, gave the perfluorinated corresponding compound, which was led to the coating material for surface treating agents, and the methyl ester of the starting perfluorinated acyl fluoride. Application to the synthesis of a new perfluorinated bifunctional sulfonate monomer CF2=CFOCF2CF2CF2OCF(CF2SO2F)2 for polymer electrolyte membranes (PEMs) of fuel cells was also developed. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
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Open AccessArticle Optimization of Fluorine Plasma Treatment for Interface Improvement on HfO2/In0.53Ga0.47As MOSFETs
Appl. Sci. 2012, 2(1), 233-244; doi:10.3390/app2010233
Received: 30 January 2012 / Revised: 20 February 2012 / Accepted: 10 March 2012 / Published: 19 March 2012
Cited by 3 | PDF Full-text (599 KB) | HTML Full-text | XML Full-text
Abstract
This paper reports significant improvements in the electrical performance of In0.53Ga0.47As metal-oxide-semiconductor field-effect transistors (MOSFET) by a post-gate CF4/O2 plasma treatment. The optimum condition of CF4/O2 plasma treatment has been systematically studied and
[...] Read more.
This paper reports significant improvements in the electrical performance of In0.53Ga0.47As metal-oxide-semiconductor field-effect transistors (MOSFET) by a post-gate CF4/O2 plasma treatment. The optimum condition of CF4/O2 plasma treatment has been systematically studied and found to be 30 W for 3–5 min. Approximately 5× reduction in interface trap density from 2.8 × 1012 to 4.9 × 1011 cm−2eV−1 has been demonstrated with fluorine (F) incorporation. Subthreshold swing has been improved from 127 to 109 mV/dec. Effective channel mobility has been enhanced from 826 to 1,144 cm2/Vs. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
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Open AccessArticle Stain Resistance of Cotton Fabrics before and after Finishing with Admicellar Polymerization
Appl. Sci. 2012, 2(1), 192-205; doi:10.3390/app2010192
Received: 18 January 2012 / Revised: 24 February 2012 / Accepted: 27 February 2012 / Published: 5 March 2012
Cited by 7 | PDF Full-text (1918 KB) | HTML Full-text | XML Full-text
Abstract
Environmental concerns related to perfluoroctanoic acid (PFOA) led to a re-examination of the methods for imparting stain resistance and stain repellency to textiles. Non-PFOA fluoropolymer finishes have been formed on cotton knits by admicellar polymerization, a surface analogue of emulsion polymerization. Fabric samples
[...] Read more.
Environmental concerns related to perfluoroctanoic acid (PFOA) led to a re-examination of the methods for imparting stain resistance and stain repellency to textiles. Non-PFOA fluoropolymer finishes have been formed on cotton knits by admicellar polymerization, a surface analogue of emulsion polymerization. Fabric samples were characterized by a drop test, contact angle measurements, SEM, elemental analysis and durability studies. Stain resistance and stain release properties were assessed by reflectance and AATCC tests with results comparing favorably with swatches from commercially available garments. Admicellar polymerization enabled the formation of durable finishes that exhibited high performance in stain resistance and stain repellency. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
Open AccessArticle Self-Assembled Fluorinated Organogelators for Surface Modification
Appl. Sci. 2012, 2(1), 175-191; doi:10.3390/app2010175
Received: 16 January 2012 / Revised: 15 February 2012 / Accepted: 21 February 2012 / Published: 1 March 2012
Cited by 5 | PDF Full-text (1655 KB) | HTML Full-text | XML Full-text
Abstract
A new class of alkyl- and perfluoroalkyl-containing urea and amide derivatives was synthesized from amino acid derivatives. Most of these compounds showed excellent gelation behavior in organic solvents at low concentrations. A few organogelators selected from the initial screening were used for surface
[...] Read more.
A new class of alkyl- and perfluoroalkyl-containing urea and amide derivatives was synthesized from amino acid derivatives. Most of these compounds showed excellent gelation behavior in organic solvents at low concentrations. A few organogelators selected from the initial screening were used for surface modification of fibrous substrates to create hydrophobic and oleophobic composites. The hydrophobic and oleophobic behaviors of these composites were ascribed to a combination of increased surface roughness and the alkyl/fluorinated functionalities present in the gelator backbone. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
Open AccessArticle Computational Study on the Acid Catalyzed Reactions of Fluorine-Containing 2,4-Dialkoxy-3,4-dihydro-2H-pyrans with Aromatic Compounds
Appl. Sci. 2012, 2(1), 129-138; doi:10.3390/app2010129
Received: 14 January 2012 / Revised: 7 February 2012 / Accepted: 13 February 2012 / Published: 24 February 2012
Cited by 2 | PDF Full-text (346 KB) | HTML Full-text | XML Full-text
Abstract
The reaction of 2,4-diethoxy-6-trifluoromethyl-3,4-dihydro-2H-pyran (1) with aromatic compounds in refluxing acetonitrile in the presence of p-toluenesulfonic acid gave the mixture of 4-aryl-2-trifluoromethyl-4H-pyrans (3) and 6-aryl-1,1,1-trifluorohexa-3,5-dien-2-ones (4). In contrast, the same reaction carried
[...] Read more.
The reaction of 2,4-diethoxy-6-trifluoromethyl-3,4-dihydro-2H-pyran (1) with aromatic compounds in refluxing acetonitrile in the presence of p-toluenesulfonic acid gave the mixture of 4-aryl-2-trifluoromethyl-4H-pyrans (3) and 6-aryl-1,1,1-trifluorohexa-3,5-dien-2-ones (4). In contrast, the same reaction carried out in trifluoroacetic acid at ambient temperature afforded 4-aryl-2-ethoxy-6-trifluoromethyl-3,4-dihydro-2H-pyrans (2) selectively. These two types of reactions giving quite different products under each condition were studied on the basis of DFT calculations. Moreover, the proposed mechanism for the reaction of 5-trifluoroacetyl-6-trifluoromethyl-3,4-dihydro-2H-pyran (5) with aromatic compounds affording butadiene derivatives (6) exclusively was also discussed based on the calculations and comparison with the reactivity of pyrylium intermediate (7). Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
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Open AccessArticle A Study of Fluorinated β-Nitrostyrenes as Antimicrobial Agents
Appl. Sci. 2012, 2(1), 114-128; doi:10.3390/app2010114
Received: 23 January 2012 / Revised: 10 February 2012 / Accepted: 14 February 2012 / Published: 23 February 2012
Cited by 6 | PDF Full-text (391 KB) | HTML Full-text | XML Full-text
Abstract
The effect of variously fluorine-substituted β-methyl-β-nitrostyrenes on their antimicrobial activity was investigated. Their efficacy was determined by minimum inhibition concentration (MIC) in cultures of Gram positive and Gram negative bacteria and a fungus. Highest activity against the Gram negative bacterium, E.coli, was
[...] Read more.
The effect of variously fluorine-substituted β-methyl-β-nitrostyrenes on their antimicrobial activity was investigated. Their efficacy was determined by minimum inhibition concentration (MIC) in cultures of Gram positive and Gram negative bacteria and a fungus. Highest activity against the Gram negative bacterium, E.coli, was achieved with 4-fluorine-aryl substituted β-methyl-β-nitrostyrenes, while most compounds gave excellent results against gram positive bacteria. Importantly, the addition of the β-methyl group profoundly enhanced the antibacterial activity of the compounds tested. The comparative KD values for the most potent compounds against E.coli were much lower than those required for the gram positive and fungus counterparts. This investigation illustrated that fluorine substituted nitropropenylarenes have enhanced antimicrobial activity suitable for antibiotic applications. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
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Open AccessArticle Novel Fluorinated Indanone, Tetralone and Naphthone Derivatives: Synthesis and Unique Structural Features
Appl. Sci. 2012, 2(1), 61-99; doi:10.3390/app2010061
Received: 6 December 2011 / Revised: 12 January 2012 / Accepted: 16 January 2012 / Published: 1 February 2012
Cited by 1 | PDF Full-text (645 KB) | HTML Full-text | XML Full-text
Abstract
Several fluorinated and trifluoromethylated indanone, tetralone and naphthone derivatives have been prepared via Claisen condensations and selective fluorinations in yields ranging from 22–60%. In addition, we report the synthesis of new, selectively fluorinated bindones in yields ranging from 72–92%. Of particular interest is
[...] Read more.
Several fluorinated and trifluoromethylated indanone, tetralone and naphthone derivatives have been prepared via Claisen condensations and selective fluorinations in yields ranging from 22–60%. In addition, we report the synthesis of new, selectively fluorinated bindones in yields ranging from 72–92%. Of particular interest is the fluorination and trifluoroacetylation regiochemistry observed in these fluorinated products. We also note unusual transformations including a novel one pot, dual trifluoroacetylation, trifluoroacetylnaphthone synthesis via a deacetylation as well as an acetyl-trifluoroacetyl group exchange. Solid-state structural features exhibited by these compounds were investigated using crystallographic methods. Crystallographic results, supported by spectroscopic data, show that trifluoroacetylated ketones prefer a chelated cis-enol form whereas fluorinated bindone products exist primarily as the cross-conjugated triketo form. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
Open AccessArticle Nanoimprint Resist Material Containing Ultraviolet Reactive Fluorine Surfactant for Defect Reduction in Lithographic Fabrication
Appl. Sci. 2012, 2(1), 24-34; doi:10.3390/app2010024
Received: 9 December 2011 / Revised: 4 January 2012 / Accepted: 5 January 2012 / Published: 16 January 2012
Cited by 8 | PDF Full-text (682 KB) | HTML Full-text | XML Full-text
Abstract
The generated resist based defects on the template in addition to the presence of particles and contaminants is critical for ultraviolet curing of nanoimprint lithographic fabrication. This procedure is proven to be suitable for advanced resist material design under the process conditions. Nanoimprint
[...] Read more.
The generated resist based defects on the template in addition to the presence of particles and contaminants is critical for ultraviolet curing of nanoimprint lithographic fabrication. This procedure is proven to be suitable for advanced resist material design under the process conditions. Nanoimprint resist material containing an ultraviolet reactive fluorine surfactant was developed to modify the fundamental surface interactions between resists and the template for defect reduction in nanoimprint patterning replication. The developed acrylate type nanoimprint resist material containing 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxyundecyl acrylate as an ultraviolet reactive fluorine surfactant, indicated excellent patterning dimensional accuracy by minimizing surface free energy, and having the effect of improving the generated resist based defect numbers on the template, with a 500 nm contact hole and 2 μm line patterns, in the replication of 20 nanoimprint process cycles. This desirable concept using an ultraviolet reactive fluorine surfactant with an acrylate group in the acrylate type nanoimprint resist material is one of the most promising processes ready to be incorporated into mass fabrication in the next generation of electronic devices. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)

Review

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Open AccessReview Overview of the Development of the Fluoropolymer Industry
Appl. Sci. 2012, 2(2), 496-512; doi:10.3390/app2020496
Received: 23 April 2012 / Revised: 3 May 2012 / Accepted: 14 May 2012 / Published: 29 May 2012
Cited by 29 | PDF Full-text (217 KB) | HTML Full-text | XML Full-text
Abstract
The present review briefly describes the development of the fluoropolymer industry in the past 70 years. Discussed are industrial fluoropolymers including polytetrafluoroethylene, polychlorotrifluoroethylene, polyvinylidenefluoride, polyvinylfluoride, ETFE, ECTFE, FEP, PFA, THV, Teflon AF and Cytop. Nafion is included as a special functional fluoropolymer material.
[...] Read more.
The present review briefly describes the development of the fluoropolymer industry in the past 70 years. Discussed are industrial fluoropolymers including polytetrafluoroethylene, polychlorotrifluoroethylene, polyvinylidenefluoride, polyvinylfluoride, ETFE, ECTFE, FEP, PFA, THV, Teflon AF and Cytop. Nafion is included as a special functional fluoropolymer material. These industrial fluoropolymers are introduced in the order of their discovery or time of first production, included are their chemical structures, thermal properties, mechanical properties, electrical and electronic properties, optical properties, chemical resistance, oxidative stabilities, weather stabilities, processabilities and their general applications. The main manufacturing companies for the different types of fluoropolymer products are also mentioned. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
Open AccessReview An Environmentally Friendly Class of Fluoropolyether: α,ω-Dialkoxyfluoropolyethers
Appl. Sci. 2012, 2(2), 351-367; doi:10.3390/app2020351
Received: 21 February 2012 / Revised: 27 March 2012 / Accepted: 27 March 2012 / Published: 11 April 2012
Cited by 6 | PDF Full-text (521 KB) | HTML Full-text | XML Full-text
Abstract
The α,ω-dialkoxyfluoropolyethers (DA-FPEs) characterized by the structure RHO(CF2CF2O)n(CF2O)mRH have been developed as a new class of environmentally friendly hydrofluoroethers (HFEs) suitable as solvents, long-term refrigerants, cleaning fluids, and heat transfer
[...] Read more.
The α,ω-dialkoxyfluoropolyethers (DA-FPEs) characterized by the structure RHO(CF2CF2O)n(CF2O)mRH have been developed as a new class of environmentally friendly hydrofluoroethers (HFEs) suitable as solvents, long-term refrigerants, cleaning fluids, and heat transfer fluids. Synthetic methodologies for DA-FPEs described here consist of radical-initiated oxypolymerization of olefin, peroxy-elimination reaction in peroxidic perfluoropolyethers (P-PFPEs) and further chemical modification of α,ω-diacylfluoride PFPE. The physical properties of selected α,ω-dimethoxyfluoropolyethers (DM-FPEs) have been evaluated and compared with analogous hydrofluoropolyethers (HFPEs) having -OCF2H as end-groups. Atmospheric implications and global warming potentials (GWPs) of selected DA-FPEs are also considered. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
Open AccessReview Silicon-[18F]Fluorine Radiochemistry: Basics, Applications and Challenges
Appl. Sci. 2012, 2(2), 277-302; doi:10.3390/app2020277
Received: 9 February 2012 / Revised: 8 March 2012 / Accepted: 19 March 2012 / Published: 28 March 2012
Cited by 17 | PDF Full-text (628 KB) | HTML Full-text | XML Full-text
Abstract
Silicon-[18F]fluorine (Si-18F) radiochemistry has recently emerged alongside other unconventional approaches such as aluminum-18F and boron-18F based labeling strategies, reshaping the landscape of modern 18F-radiochemistry. All these novel methodologies are driven by the demand for
[...] Read more.
Silicon-[18F]fluorine (Si-18F) radiochemistry has recently emerged alongside other unconventional approaches such as aluminum-18F and boron-18F based labeling strategies, reshaping the landscape of modern 18F-radiochemistry. All these novel methodologies are driven by the demand for more convenient 18F-labeling procedures to further disseminate one of the most sophisticated imaging technologies, Positron Emission Tomography (PET). The PET methodology requires special radionuclides such as 18F (one of the most prominent examples) to be introduced into bioactive molecules. Si-18F radiochemistry contributed greatly towards the development of new radiopharmaceuticals for PET imaging. Herein, we describe the radiochemical basics of Si-18F bond formation, the application of Si-18F tracers for PET imaging, and additionally, the inherent chemical intricacies of this methodology. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
Open AccessReview Nucleic Acid Based Fluorinated Derivatives: New Tools for Biomedical Applications
Appl. Sci. 2012, 2(2), 245-259; doi:10.3390/app2020245
Received: 14 January 2012 / Revised: 13 March 2012 / Accepted: 14 March 2012 / Published: 23 March 2012
Cited by 7 | PDF Full-text (1250 KB) | HTML Full-text | XML Full-text
Abstract
Nucleic acid-based fluorinated derivatives, e.g., nucleosides or oligonucleotides connected to highly fluorinated chains or labeled with one or more fluorine atoms, have been investigated recently due to their high potential for biomedical applications. This review deals with recent works on nucleoside and oligonucleotide
[...] Read more.
Nucleic acid-based fluorinated derivatives, e.g., nucleosides or oligonucleotides connected to highly fluorinated chains or labeled with one or more fluorine atoms, have been investigated recently due to their high potential for biomedical applications. This review deals with recent works on nucleoside and oligonucleotide fluorocarbon amphiphiles as well as with properties and applications of fluorine-labeled oligonucleotide analogues. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
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Open AccessReview Oxyfluoride Chemistry of Layered Perovskite Compounds
Appl. Sci. 2012, 2(1), 206-219; doi:10.3390/app2010206
Received: 14 February 2012 / Revised: 22 February 2012 / Accepted: 28 February 2012 / Published: 6 March 2012
Cited by 24 | PDF Full-text (5398 KB) | HTML Full-text | XML Full-text
Abstract
In this paper, we review recent progress and new challenges in the area of oxyfluoride perovskite, especially layered systems including Ruddlesden-Popper (RP), Dion-Jacobson (DJ) and Aurivillius (AV) type perovskite families. It is difficult to synthesize oxyfluoride perovskite using a conventional solid-state reaction because
[...] Read more.
In this paper, we review recent progress and new challenges in the area of oxyfluoride perovskite, especially layered systems including Ruddlesden-Popper (RP), Dion-Jacobson (DJ) and Aurivillius (AV) type perovskite families. It is difficult to synthesize oxyfluoride perovskite using a conventional solid-state reaction because of the high chemical stability of the simple fluoride starting materials. Nevertheless, persistent efforts made by solid-state chemists have led to a major breakthrough in stabilizing such a mixed anion system. In particular, it is known that layered perovskite compounds exhibit a rich variety of O/F site occupation according to the synthesis used. We also present the synthetic strategies to further extend RP type perovskite compounds, with particular reference to newly synthesized oxyfluorides, Sr2CoO3F and Sr3Fe2O5+xF2x (x ~ 0.44). Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
Open AccessReview Enhancement of Brillouin Scattering Signal in Perfluorinated Graded-Index Polymer Optical Fibers
Appl. Sci. 2012, 2(1), 46-60; doi:10.3390/app2010046
Received: 26 December 2011 / Revised: 18 January 2012 / Accepted: 20 January 2012 / Published: 31 January 2012
Cited by 1 | PDF Full-text (357 KB) | HTML Full-text | XML Full-text
Abstract
Perfluorinated graded-index polymer optical fibers (PFGI-POFs), fabricated by replacing the hydrogen atoms of standard polymethyl methacrylate-based POFs with fluorine atoms, have been extensively studied due to their relatively low propagation loss even at telecommunication wavelength. Recently, Brillouin scattering, which is one of the
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Perfluorinated graded-index polymer optical fibers (PFGI-POFs), fabricated by replacing the hydrogen atoms of standard polymethyl methacrylate-based POFs with fluorine atoms, have been extensively studied due to their relatively low propagation loss even at telecommunication wavelength. Recently, Brillouin scattering, which is one of the most significant nonlinear effects in optical fibers, has been successfully observed in PFGI-POFs at 1.55-μm wavelength. The Brillouin Stokes signal was, however, not large enough for practical applications or for detailed investigations of the Brillouin properties. In this paper, we review our recent work on Stokes signal enhancement. First, we induce stimulated Brillouin scattering based on the so-called pump-probe technique, and discuss its applicability to temperature sensors. Then, we investigate the influence of the core diameter and length of PFGI-POFs on Stokes signal, and observe the Brillouin linewidth narrowing effect. We believe our work is an important technological step toward the implementation of practical Brillouin-based devices and systems including distributed strain and temperature sensors. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)

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