Fluorous Research Articles

Separation of metallic and semiconducting single-walled carbon nanotubes through fluorous chemistry

Separation of metallic from semiconducting single-walled carbon nanotubes has been a major challenge for some time and some previous efforts have resulted in partial success. We have accomplished the separation effectively by employing fluorous chemistry wherein the diazonium salt of 4-heptadecafluorooc tylaniline selectively reacts with the metallic nanotubes present in the mixture of nanotubes. The resulting fluoroderivative was extracted in perfluorohexane leaving the semiconducting nanotubes in the aqueous layer. The products have been characterized by both Raman and electronic absorption spectroscopy. The method avoids the cumbersome centrifugation step required by some other procedures.

An alternative and facile purification procedure of amidation and esterification reactions using a medium fluorous Mukaiyama reagent

A convenient methodology for the separation of a fluorous by-product using fluorous chemistry is described. A Mukaiyama coupling reagent bearing a medium fluorous tag, between 40% and 60% fluorine by weight, can be effectively separated from non-fluorous components by increasing the water content of the crude reaction mixture and subsequent filtration. Additional fluorous solid phase extraction is not necessary.

ChemInform Abstract: Fluorous Chemistry for Synthesis and Purification of Biomolecules: Peptides, Oligosaccharides, Glycopeptides, and Oligonucleotides

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Second-Generation Tags for Fluorous Chemistry Exemplified with a New Fluorous Mitsunobu Reagent

A new fluorous DEAD reagent bearing two perfluoro-tert-butyloxy groups with propylene spacers shows excellent promise for use in fluorous Mitsunobu reactions. Pure target products were obtained in good yields after removing fluorous byproducts by FSPE. The new reagent serves as a prototype for a greener second generation of fluorous reagents bearing tags that are not expected to degrade in the environment to compounds that are highly persistent or that bioaccumulate in higher organisms.

HFPO Trimer-Based Alkyl Triflate, a Novel Building Block for Fluorous Chemistry. Preparation, Reactions and 19F gCOSY Analysis

Triflate 4, CF3(CF2)2O-CF(CF3)CF2O-CF(CF3)CH2-OTf (RFOCH2OTf), of the HFPO trimer-based alcohol 3 (RFOCH2OH) is a novel highly fluorinated building block for fluorous chemistry. In analogy to similar polyfluorinated triflates with methylene spacer, its reactivity is limited to strong and soft nucleophiles. Whereas reactions with cyanide anion, phenolate anion, enolate of diethyl malonate or lithium salt of benzaldehyde bis(phenylsulfanyl)acetal were unsuccessful, the corresponding imidazole 5, iodide 6 or azide 7 were prepared in good yields. Reaction of imidazole 5 with (perfluorohexyl)methyl triflate (9) afforded highly fluorinated non-crystalline imidazolium salt 8, TfO-RFOCH2-(C3H3N2)+-CH2C6F13-n, which could be employed as fluorous ionic liquid or intermediate for fluorous carbenes. Complete assignment of complex 19F NMR spectra of all compounds employed was accomplished using 19F gCOSY NMR method.

3‐(Perfluoroalkyl)propanols: Valuable Building Blocks for Fluorous Chemistry.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Recent Applications of Fluorous Separation Methods in Organic and Bioorganic Chemistry

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Separations and Syntheses of Chiral Compounds and Application to the Synthesis of Natural Products Using Fluorous Chemistry

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Use of Fluorous Chemistry in the Solubilization and Phase Transfer of Nanocrystals, Nanorods, and Nanotubes

Fluorous chemistry, involving the use of a fluorous label for the functionalization of a substrate and a fluorous solvent for extraction of the functionalized substrate, is shown to be effective in solubilizing gold and CdSe nanoparticles in a fluorous medium, through phase transfer from an aqueous or a hydrocarbon medium. While these nanoparticles were functionalized with a fluorous thiol, single-walled carbon nanotubes and ZnO nanorods could be solubilized in a fluorous medium by reacting them with a fluorous amine. Fluorous chemistry enables the solubilization of the nanostructures in the most nonpolar liquid medium possible.

FLUOROUS PHASE IN A CAGE

MOST CHEMISTS WOULD CONsider a 5-mL round-bottom 1 flask an appropriate vessel for a small-scale reaction. But for the researchers in Makoto Fujita's lab, that's about a million times too big. Fujita, a chemistry professor at the University of Tokyo, and his colleagues have been making nanoscale reaction chambers just 5 nm wide. Their latest invention—a tiny cage lined with 24 perfruorinated carbon chaim—offers a finery tuned environment for fluorous chemistry ( Science 2006,313 ,1273) There are many other examples of fluorous microenvironments, notes chemistry professor John A. Gladysz of Friedrich-Alexander University, Erlangen, Germany, in a commentary on the report. However, none of these assemblies features the elegant design elements and the degree of molecular control that characterize,, Fujita's complexes. Fujita's team designed an arrow- shaped molecule as their structure's basic building block. A bridging ligand forms the arrowhead, which attaches to a long fluorocarbon tail. In solution, 24 of...

Recent Applications of Fluorous Separation Methods in Organic and Bioorganic Chemistry

AbstractInitially introduced as a niche technique to recover and recycle catalysts, fluorous chemistry has rapidly expanded into organic synthesis and combinatorial chemistry over the past 12 years. Recently, fluorous methods are also enabling purification of biomolecules such as peptides, oligosaccharides, and oligonucleotides assembled by traditional solid‐phase synthesis. Apart from synthetic applications, fluorous chemistry is also providing solutions for critical problems in proteomics and microarray chip technology. This review highlights selected recent advances that underscore the impact of fluorous separation methods in organic and bioorganic chemistry.

Tiny Fluorous Flasks

Tiny Fluorous Flasks

Fluorous Chemistry: From Biphasic Catalysis to High‐Throughout Synthesis of Small Molecules and Separation/Immobilization of Biomolecules

QSAR & Combinatorial ScienceVolume 25, Issue 8-9 p. 679-679 EditorialFree Access Fluorous Chemistry: From Biphasic Catalysis to High-Throughout Synthesis of Small Molecules and Separation/Immobilization of Biomolecules First published: 08 September 2006 https://doi.org/10.1002/qsar.200690023Citations: 6AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article.Citing Literature Volume25, Issue8-9Special Issue: Fluorous ChemistrySeptember 2006Pages 679-679 RelatedInformation

Self‐Assembly of Hybrid Fluorous Materials

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Novel generation ponytails in fluorous chemistry: Syntheses of primary, secondary, and tertiary (nonafluoro- tert-butyloxy)ethyl amines

(Nonafluoro- tert-butyloxy)ethyl tosylate 4 was prepared in 65% yield from nonafluoro- tert-butanol 1 using commercially available reagents. Further reaction of 4 with HNR 1R 2 (R 1 = R 2 = H, CH 3; R 1 = H, R 2 = CH 3, (CH 2) 3C 8F 17, CH 2CH 2OC(CF 3) 3) affords the appropriate (CF 3) 3COCH 2CH 2NR 1R 2 amines in 20–69% yields. Improved overall yields of [(CF 3) 3COCH 2CH 2] 3− n NR n to 1 were obtained by the reaction of (CF 3) 3CONa 2 and (XCH 2CH 2) 3− n NR n (X = Cl, n = 0, 1, 2, R = CH 3; X = CH 3SO 2O, n = 1, R = CH 3SO 2) nitrogen mustards and a similar reactive β-substituted ethyl amine. The title amines are mobile colorless liquids and volatile with steam. The bulky fluorous ponytail (CF 3) 3CO(CH 2) 2 displays high acidic stability and increases fluorous character almost as much as the classical straight-chain C 8F 17(CH 2) 3 ponytail.

Microwave‐Assisted Fluorous Chemistry

AbstractFor Abstract see ChemInform Abstract in Full Text.

A Personal View of the History of Fluorous Chemistry

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Handbook of Fluorous Chemistry. Edited by J. A. Gladysz, D. P. Curran, I. T. Horváth

Advanced Synthesis & CatalysisVolume 347, Issue 10 p. 1451-1451 Book Review Handbook of Fluorous Chemistry. Edited by J. A. Gladysz, D. P. Curran, I. T. Horváth Berth-Jan Deelman, Berth-Jan Deelman ARKEMA Vlissingen B.V., P.O.Box 70, 4380 AB Vlissingen, The Netherlands, Phone: (31)-(0)113-617-000, Fax: (31)-(0)113-612-984Search for more papers by this author Berth-Jan Deelman, Berth-Jan Deelman ARKEMA Vlissingen B.V., P.O.Box 70, 4380 AB Vlissingen, The Netherlands, Phone: (31)-(0)113-617-000, Fax: (31)-(0)113-612-984Search for more papers by this author First published: 22 August 2005 https://doi.org/10.1002/adsc.200505124AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume347, Issue10August 2005Pages 1451-1451 RelatedInformation

Fluorous Glycopeptide Synthesis Without Protection of Sugar Hydroxy Groups.

ChemInformVolume 36, Issue 31 Natural Products Fluorous Glycopeptide Synthesis Without Protection of Sugar Hydroxy Groups. Mamoru Mizuno, Mamoru Mizuno Lab. Glycoorg. Chem., Noguchi Inst., Itabashi, Tokyo 173, JapanSearch for more papers by this authorKohtaro Goto, Kohtaro Goto Lab. Glycoorg. Chem., Noguchi Inst., Itabashi, Tokyo 173, JapanSearch for more papers by this authorTsuyoshi Miura, Tsuyoshi Miura Lab. Glycoorg. Chem., Noguchi Inst., Itabashi, Tokyo 173, JapanSearch for more papers by this author Mamoru Mizuno, Mamoru Mizuno Lab. Glycoorg. Chem., Noguchi Inst., Itabashi, Tokyo 173, JapanSearch for more papers by this authorKohtaro Goto, Kohtaro Goto Lab. Glycoorg. Chem., Noguchi Inst., Itabashi, Tokyo 173, JapanSearch for more papers by this authorTsuyoshi Miura, Tsuyoshi Miura Lab. Glycoorg. Chem., Noguchi Inst., Itabashi, Tokyo 173, JapanSearch for more papers by this author First published: 19 July 2005 https://doi.org/10.1002/chin.200531167AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume36, Issue31August 2, 2005 RelatedInformation

Handbook of Fluorous Chemistry. Edited by John A. Gladysz, Dennis P. Curran and István Horváth.

Handbook of Fluorous Chemistry. Edited by John A. Gladysz, Dennis P. Curran and István Horváth.