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Volumn 15, Issue 47, 2005, Pages 4981-4991

New fluorinated functional materials

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGY; CATALYSIS; HYDROPHOBICITY; POLYCONDENSATION;

EID: 29244447697     PISSN: 09599428     EISSN: 13645501     Source Type: Journal    
DOI: 10.1039/b507583c     Document Type: Article
Times cited : (227)

References (76)
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    • The US chemicals supplier Sigma Aldrich, for instance, offers a wide variety of such reactants. See the company's publication: ChemFiles, 2005, 49.
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    • For a recent book dealing with the aspects of the importance of fluorine in organic synthesis, see: (a) R. D. Chambers, Fluorine in Organic Chemistry, Blackwell Publishing, Oxford, UK, 2004. A thematic issue dedicated to fluorous chemistry was recently published in:
    • (2004) Fluorine in Organic Chemistry
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    • (b) Tetrahedron, 2002, 58, 3823-413. For a thorough recent review on synthetic fluorine chemistry, see:
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    • 2F), and in aromatic halogen exchange, the industrial route to make fluorinated aromatic building blocks: H. Sun and S. G. DiMagno, J. Am. Chem. Soc., 2005, 127, 2050.
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    • Sun, H.1    DiMagno, S.G.2
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    • note
    • The hydrophobic nature of fluorinated compounds often causes improved transport across the blood brain barrier. Improved oral bioavailability is seen in some systems where fluorine substitution leads to improved hydrolytic stability. Furthermore, replacement of sensitive or reactive groups such as C-OH, C-H, and C=O with fluorinated substituents has led to mechanism-based inhibitors for a wide variety of diseases and to chemotherapeutic drugs.
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    • For an overview of the numerous applications of PTFE, see at the URL: http://www.teflon.com/.
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    • However, there are important exceptions. For a subset of compounds, the replacement of hydrogen by fluorine results in a significant lowering of their lipophilicity due to the fact that these compounds contain an oxygen functionality in close proximity to the fluorine substitution site leading to better solvation of the fluorinated compound in water: H.-J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander and M. Stahl, ChemBioChem, 2004, 5, 637.
    • (2004) ChemBioChem , vol.5 , pp. 637
    • Böhm, H.-J.1    Banner, D.2    Bendels, S.3    Kansy, M.4    Kuhn, B.5    Müller, K.6    Obst-Sander, U.7    Stahl, M.8
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    • note
    • 3) centers always withdraw electrons to destabilize cations and to stabilize anions.
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    • J. C. Biffinger, H. W. Kim and S. G. DiMagno, ChemBioChem, 2004, 5, 622. The authors explain the biochemistry of fluorinated substances, showing how a cooperative polar hydrophobic effect takes place in which extensive fluorine substitution for polar hydrophilic groups may increase the free energy of binding as the hydrophobic fluorocarbon surface, upon transfer to the receptor, liberates water molecules to the bulk solvent (entropically favoured) while concomitantly, enthalpically favorable dipolar interactions of the C-F bonds with cationic or dipolar residues in the receptor site are retained.
    • (2004) ChemBioChem , vol.5 , pp. 622
    • Biffinger, J.C.1    Kim, H.W.2    Dimagno, S.G.3
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    • Thus, molecular dynamics simulations on mixtures involving water, hydrocarbons, and a variety of fluorinated molecules are currently carried out with the purpose of understanding the nature of the fluorous phase and to establish what kind of intermolecular forces can explain the formation of different phases at the University of Wisconsin at Madison by Professor Sandro Mecozzi's research group. S. Mecozzi, personal communication (March 2005).
    • (2005)
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    • For an account on the impressive variety of applications of doped silica gels only, see: D. Avnir, L. C. Klein, D. Levy, U. Schubert and A. B. Wojcik in The Chemistry of Organosilicon Compounds, ed. Y. Apeloig and Z. Rappoport, Wiley & Sons, Chichester, 1998, vol. 2, pp. 2317-2362.
    • (1998) The Chemistry of Organosilicon Compounds , vol.2 , pp. 2317-2362
    • Avnir, D.1    Klein, L.C.2    Levy, D.3    Schubert, U.4    Wojcik, A.B.5
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    • Hydrolytically stable fluorinates are indeed easily synthesized and commercially available in an ample variety. Along with Fluorochem, Apollo, FTI chemicals manufacturer ABCR commercializes a variety of such fluorinated metal alkoxides. See: http://www.abcr.de/.
  • 45
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    • "Inverse opal" silica films are obtained adding polystyrene spheres several hundred micrometres in diameter to the silica alkoxide and surfactant precursor sol at the onset of the sol-gel polycondensation. The mixture self-assembles into a regular hexagonal array with the smaller silica particles filling in the gaps between the closely packed polystyrene spheres, in: Z.-Z. Gu, H. Uetsuka, K. Takahashi, R. Nakajima, H. Onishi, A. Fujishima and O. Sato, Angew. Chem. Int. Ed., 2003, 42, 894.
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    • Gu, Z.-Z.1    Uetsuka, H.2    Takahashi, K.3    Nakajima, R.4    Onishi, H.5    Fujishima, A.6    Sato, O.7
  • 46
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    • The US based company Fluorous Technologies commercializes a wide variety of fluorinated molecules and materials including those of Sigma Aldrich. See: http://www.fluorous.com.
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    • Analogous ORMOSIL-entrapped lipases used by industry, for instance, are coated on SIRAN glass beads: M. T. Reetz, Adv. Mater., 1997, 9, 943. Indeed, the patented discovery of absorbtive fluorinated ORMOSIL (ref. 3) reports coating the gels over granulated active charcoal and similar cheap porous materials.
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    • Reetz, M.T.1
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    • 29244454784 scopus 로고    scopus 로고
    • Carrying out a continuous conversion in carbon dioxide allows the kinetic control of the reaction and since mid 2002 the British fine chemicals manufacturer Thomas Swan & Co. Ltd. produces a host of fine chemicals with striking selectivity (and purity) in the first multipurpose plant for heterogeneously catalyzed productions in the world. See: http://www.thomas-swan. co.uk.
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    • For instance, a new easy-to-use hand-held optical sol-gel oxygen sensor (named FOXY-LITE, see: http://www.oceanoptics.com) with a response time of less than 1 s has been commercialized at $1,999 since March 2004 by the US company Ocean Optics Ltd. The sensor uses a fluorescent ruthenium complex immobilized in a silica sol-gel matrix at the probe's tip. Fluorination of the sol-gel matrix described in ref. 9, however, enhances both sensitivity and stability of the sensor and is likely to be adopted soon by the company.
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    • note
    • Most big chemical companies produce increasing amounts of fluorinated polymers as high value-added chemicals. For instance, former Italian company Ausimont (now owned by Solvay), in the year 2000 had a revenue of 490 million euros and almost 100 million euros of net tax profit selling fluorinated organics produced in eight plants (three in Italy, one in Germany and four in the US).
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    • For an interesting account on the environmental effects of fluorinated organics, see: (b) R. Renner, Environ. Sci. Technol., 2001, 37, 154A.
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    • Renner, R.1
  • 71
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    • note
    • 2 marketed in the US since 1995 by Micell Technologies in partnership with the Hangers chain of dry cleaners (with stores using the technology in the US, Canada and two EU member States as of March 2005).
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    • Little Brown and Company, New York
    • This refers to a new management approach to the environmental issues started in the mid 1980s with environmental certification programs such as Responsible Care, ISO 14001 and Emas, and evolved into the concept of sustainability as a central issue to be managed at the board level aiming at Zero Emissions performance level. See also: P. Hawken, A. Lovins and L. H. Lovins, Natural Capitalism: Creating the Next Industrial Revolution, Little Brown and Company, New York, 1999.
    • (1999) Natural Capitalism: Creating the next Industrial Revolution
    • Hawken, P.1    Lovins, A.2    Lovins, L.H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.