메뉴 건너뛰기




Volumn 36, Issue 2, 2009, Pages 247-257

A conceptual design of fluorous surfactants based on a heterocyclic core, put into practice through synthesis of fluorous 1,2,3-triazoles

Author keywords

Click chemistry; Fluorous chemistry; Heterocycles; Organic Synthesis; Polyfluoroalkyl 1,2,3 Triazoles; Surfactants

Indexed keywords


EID: 67650704196     PISSN: 01252526     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (15)

References (32)
  • 1
    • 0035465476 scopus 로고    scopus 로고
    • Oxygen carriers(blood substitutes). raison d'etre, chemistry, and some physiology
    • Riess J.G., Oxygen Carriers ("Blood Substitutes"). Raison d'Etre, Chemistry, and Some Physiology, Chem. Rev., 2001; 101: 2797-12790
    • (2001) Chem. Rev. , vol.101 , pp. 2797-12790
    • Riess, J.G.1
  • 2
    • 0032073711 scopus 로고    scopus 로고
    • Highly fluorinated amphiphiles colloidal systems and their applications in the biomedical field. A Contribution
    • Krafft M.P. and Riess J.G., Highly Fluorinated Amphiphiles and Colloidal Systems, and Their Applications in the Biomedical Field. A Contribution, Biochimie, 1998; 80: 489-495
    • (1998) Biochimie , vol.80 , pp. 489-495
    • Krafft, M.P.1    Riess, J.G.2
  • 3
    • 0032143835 scopus 로고    scopus 로고
    • Fluorinated materials for in vivo oxygen transport (Blood Substitutes), diagnosis and drug delivery
    • Riess J.G. and Krafft M.P., Fluorinated Materials for in vivo Oxygen Transport (Blood Substitutes), Diagnosis and Drug Delivery, Biomaterials, 1998; 19: 1529-1593.
    • (1998) Biomaterials , vol.19 , pp. 1529-1593
    • Riess, J.G.1    Krafft, M.P.2
  • 8
    • 54749135449 scopus 로고    scopus 로고
    • Fluoropolymer-based emulsions for the intravenous delivery of sevoflurane
    • Fast J.P., Perkins M.G., Pearce, R.A. and Mecozzi S., Fluoropolymer-Based Emulsions for the Intravenous Delivery of Sevoflurane, Anesthesiology, 2008; 109: 651-656.
    • (2008) Anesthesiology , vol.109 , pp. 651-656
    • Fast, J.P.1    Perkins, M.G.2    Pearce, R.A.3    Mecozzi, S.4
  • 9
    • 34248532167 scopus 로고    scopus 로고
    • Synthesis and pH-dependent self-assembly of semifluorinated calix[4]arenes
    • DOI 10.1016/j.tet.2007.04.030, PII S0040402007006606
    • Martin O.M. and Mecozzi S., Synthesis and pH-Dependent Self-Assembly of Semifluorinated Calix[4]arenes, Tetrahedron, 2007; 63: 5539-5547. (Pubitemid 46755342)
    • (2007) Tetrahedron , vol.63 , Issue.25 , pp. 5539-5547
    • Martin, O.M.1    Mecozzi, S.2
  • 10
    • 34247616771 scopus 로고    scopus 로고
    • Synthesis and self-assembly properties of a novel [poly(ethylene glycol)]-fluorocarbon-phospholipid triblock copolymer
    • DOI 10.1016/j.tetlet.2007.03.148, PII S0040403907006107
    • Slaughter J.N., Schmidt K.M., Byram J.L. and Mecozzi S., Synthesis and Self- Assembly Properties of a Novel [Poly(ethyleneglycol)]-Fluorocarbon Phospholipid Triblock Copolymer, Tetrahedron Lett., 2007; 48: 3879-3882. (Pubitemid 46669651)
    • (2007) Tetrahedron Letters , vol.48 , Issue.22 , pp. 3879-3882
    • Slaughter, J.N.1    Schmidt, K.M.2    Byram, J.L.3    Mecozzi, S.4
  • 11
    • 27444440798 scopus 로고    scopus 로고
    • Solution self-assembly and solid state properties of fluorinated amphiphilic calix[4]arenes
    • DOI 10.1039/b506781b
    • Martin O.M., Yu L. and Mecozzi S., Solution Self-Assembly and Solid State Properties of Fluorinated Amphiphilic Calix[4]arenes, Chem. Commun., 2005; 4964-4966. (Pubitemid 41531754)
    • (2005) Chemical Communications , Issue.39 , pp. 4964-4966
    • Martin, O.M.1    Yu, L.2    Mecozzi, S.3
  • 12
    • 0034631787 scopus 로고    scopus 로고
    • Carbohydrate- and related polyol-derived fluorosurfactants: An update
    • DOI 10.1016/S0008-6215(00)00012-4, PII S0008621500000124
    • Riess J.G. and Greiner J., Carbohydrateand Related Polyol-Derived Fluorosurfactants: An Update, Carbohydr. Res., 2000; 327: 147-168. (Pubitemid 30625002)
    • (2000) Carbohydrate Research , vol.327 , Issue.1-2 , pp. 147-168
    • Riess, J.G.1    Greiner, J.2
  • 13
    • 0037454701 scopus 로고    scopus 로고
    • Perfluoroalkanes
    • Standford G., Perfluoroalkanes, Tetrahedron, 2003; 59: 437-454.
    • (2003) Tetrahedron , vol.59 , pp. 437-454
    • Standford, G.1
  • 14
    • 18644379454 scopus 로고    scopus 로고
    • Highly fluoroalkylated amphiphilic triazoles: Regioselective synthesis and evaluation of physicochemical Properties
    • Mayot E., Ǵrardin-Charbonnier C. and Selve, C., Highly Fluoroalkylated Amphiphilic Triazoles: Regioselective Synthesis and Evaluation of Physicochemical Properties, J. Fluorine Chem., 2005; 126: 715-720.
    • (2005) J. Fluorine Chem. , vol.126 , pp. 715-720
    • Mayot, E.1    Ǵrardin-Charbonnier, C.2    Selve, C.3
  • 15
    • 0000249401 scopus 로고    scopus 로고
    • Elaboration and specific properties of fluorinated liposomes and related supramolecular systems
    • Krafft M.P. and Riess J.G., Elaboration and Specific Properties of Fluorinated Liposomes and Related Supramolecular Systems, Cellul. Molec. Biol. Lett., 1996; 1: 459-468. (Pubitemid 126498201)
    • (1996) Cellular and Molecular Biology Letters , vol.1 , Issue.4 , pp. 459-468
    • Krafft, M.P.1    Riess, J.G.2
  • 16
    • 0028561843 scopus 로고
    • Fluorinated vesicles
    • Riess J.G., Fluorinated Vesicles, J. Drug Target., 1994; 2: 455-468.
    • (1994) J. Drug Target. , vol.2 , pp. 455-468
    • Riess, J.G.1
  • 17
    • 0028076772 scopus 로고
    • Vesicles and other supramolecular systems from biocompatible synthetic glycolipids with hydrocarbon and/or fluorocarbon chains
    • DOI 10.1016/0009-3084(94)90099-X
    • Guedj C., Pucci B., Zarif L., Coulomb C., Riess J.G. and Pavia A.A., Vesicles and Other Supramolecular Systems from Biocompatible Synthetic Glycolipids with Hydrocarbon and/or Fluorocarbon Chains, Chem. Phys. Lipids, 1994; 72: 153-173. (Pubitemid 24280240)
    • (1994) Chemistry and Physics of Lipids , vol.72 , Issue.2 , pp. 153-173
    • Guedj, C.1    Pucci, B.2    Zarif, L.3    Coulomb, C.4    Riess, J.G.5    Pavia, A.A.6
  • 18
    • 0011931317 scopus 로고
    • Synthesis of new perfluoroalkylated zwitterionic carboxybetaines. influence of the presence and position of a hydroxyl group on their solubility and biocompatibility
    • Nivet J.-B., Le Blanc M., Haddach M., Lanier M., Pastor R. and Riess J.G., Synthesis of New Perfluoroalkylated Zwitterionic Carboxybetaines. Influence of the Presence and Position of a Hydroxyl Group on their Solubility and Biocompatibility, New J. Chem., 1994; 18: 861-869.
    • (1994) New J. Chem. , vol.18 , pp. 861-869
    • Nivet, J.-B.1    Le Blanc, M.2    Haddach, M.3    Lanier, M.4    Pastor, R.5    Riess, J.G.6
  • 20
    • 33748238041 scopus 로고
    • Can single-chain perfluoroalkylated amphiphiles alone form vesicles and other organized supramolecular systems?
    • Krafft M.P., Giulieri F. and Riess J.G., Can Single Chain Perfluorinated Amphiphilic Single Vesicles and Others Form Organized Supramolecular Aggregates? Angew. Chem., Int. Ed. Engl., 1993; 32: 741-743. (Pubitemid 23978558)
    • (1993) Angewandte Chemie (International Edition in English) , vol.32 , Issue.5 , pp. 741-743
    • Krafft, M.-P.1    Giulieri, F.2    Riess, J.G.3
  • 21
    • 23344445780 scopus 로고    scopus 로고
    • Fluorous click chemistry as a practical tagging method
    • DOI 10.1039/b504973c
    • Kaleta Z., Egyed O. and So s T., Fluorous Click Chemistry as a Practical Tagging Method, Org. Biomol. Chem., 2005; 3: 2228-2230. (Pubitemid 41100369)
    • (2005) Organic and Biomolecular Chemistry , vol.3 , Issue.12 , pp. 2228-2230
    • Kaleta, Z.1    Egyed, O.2    Soos, T.3
  • 22
    • 4644326987 scopus 로고    scopus 로고
    • Regioselective synthesis of fluoroalkylated [1,2,3]-triazoles by huisgen cycloaddition
    • Wu Y.M., Deng J., Fang X. and Chen Q.Y., Regioselective Synthesis of Fluoroalkylated [1,2,3]-Triazoles by Huisgen Cycloaddition, J. Fluorine Chem., 2004; 125: 1415-1423.
    • (2004) J. Fluorine Chem. , vol.125 , pp. 1415-1423
    • Wu, Y.M.1    Deng, J.2    Fang, X.3    Chen, Q.Y.4
  • 23
    • 0037019962 scopus 로고    scopus 로고
    • Syntheses and reactivities of disubstituted and trisubstituted fluorous pyridines with high fluorous phase affinities: solid state, liquid crystal, and ionic liquid-phase properties
    • Rocaboy C, Hampel F. and Gladysz J.A., Syntheses and Reactivities of Disubstituted and Trisubstituted Fluorous Pyridines with High Fluorous Phase Affinities: Solid State, Liquid Crystal, and Ionic Liquid-Phase Properties, J. Org. Chem., 2004; 67: 6863-6870.
    • (2004) J. Org. Chem. , vol.67 , pp. 6863-6870
    • Rocaboy C1    Hampel, F.2    Gladysz, J.A.3
  • 25
    • 35948956682 scopus 로고    scopus 로고
    • Molecular aggregates of partially fluorinated quaternary ammonium salt gemini surfactants
    • DOI 10.1021/la701525c
    • Matsuoka K., Yoshimura T., Shikimoto T., Hamada J., Yamawaki M., Honda C. and Endo K., Molecular Aggregates of Partially Fluorinated Quaternary Ammonium Salt Gemini Surfactants, Langmuir, 2007; 23: 10990-10994. (Pubitemid 350069316)
    • (2007) Langmuir , vol.23 , Issue.22 , pp. 10990-10994
    • Matsuoka, K.1    Yoshimura, T.2    Shikimoto, T.3    Hamada, J.4    Yamawaki, M.5    Honda, C.6    Endo, K.7
  • 27
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry diverse chemical function from a few good reactions
    • Kolb H.C., Finn M.G. and Sharpless K.B., Click Chemistry: Diverse Chemical Function from a Few Good Reactions, Angew. Chem., Int. Ed., 2001; 40: 2004-2021.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 28
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • DOI 10.1021/jo011148j
    • Torn e C.W., Christensen C. and Meldal M., Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper (I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides, J. Org. Chem., 2002; 67: 3057-3064. (Pubitemid 34457265)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.9 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 29
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes
    • DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
    • Rostovtsev V.V., Green L.G., Fokin V.V. and Sharpless K.B., A Stepwise Huisgen Cycloaddition Process: Copper(I)- Catalyzed Regioselective Ligation of Azides and Terminal Alkynes, Angew. Chem., Int. Ed., 2002; 41: 2596-2599. (Pubitemid 34803480)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.14 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 30
    • 17644414186 scopus 로고    scopus 로고
    • I-catalyzed azide-alkyne cycloaddition reaction
    • DOI 10.1002/anie.200461496
    • Rodionov V.O., Fokin V.V. and Finn M.G., Mechanism of the Ligand-Free CuI-Catalyzed Azide-Alkyne Cycloaddition Reaction, Angew. Chem., Int. Ed., 2005; 44: 2210-2215. (Pubitemid 40560884)
    • (2005) Angewandte Chemie - International Edition , vol.44 , Issue.15 , pp. 2210-2215
    • Rodionov, V.O.1    Fokin, V.V.2    Finn, M.G.3
  • 31
    • 8744304751 scopus 로고    scopus 로고
    • One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides
    • DOI 10.1021/ol048859z
    • Feldman A.K., Colasson B. and Fokin V.V., One-Pot Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from in situ Generated Azides, Org. Lett., 2004; 22: 3897-3899. (Pubitemid 39523247)
    • (2004) Organic Letters , vol.6 , Issue.22 , pp. 3897-3899
    • Feldman, A.K.1    Colasson, B.2    Fokin, V.V.3
  • 32
    • 0027053259 scopus 로고
    • Synthesis and bioacceptability of fluorinated surfactants derived from F-alkylated tertiary amines
    • DOI 10.1016/0223-5234(92)90020-2
    • Nivet J.B., Bernelin R., Le Blanc M. and Riess J.G., Synthesis and Bioacceptability of Fluorinated Surfactants Derived from F-Alkylated Tertiary Amines, Eur. J. Med. Chem., 1992; 27: 891-898. (Pubitemid 23054398)
    • (1992) European Journal of Medicinal Chemistry , vol.27 , Issue.9 , pp. 891-898
    • Nivet, J.B.1    Bernelin, R.2    Le Blanc, M.3    Riess, J.G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.