RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2005(18): 3051-3058
DOI: 10.1055/s-2005-916026
DOI: 10.1055/s-2005-916026
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Organic Thiosulfates Tailored for the Electrochemical Deposition of ‘Self-Assembled Monolayers’ at Gold Surfaces
Weitere Informationen
Received
28 April 2005
Publikationsdatum:
16. September 2005 (online)
Publikationsverlauf
Publikationsdatum:
16. September 2005 (online)
Abstract
The synthesis of organic thiosulfates, up to 10 nm in length, which were tailored for generating artificial monomembranes on gold surfaces by electrochemically initiated deposition, was accomplished. (E)-3-(4-Hydroxyphenyl)acrylic acid (4-hydroxy cinnamic acid) was employed as aromatic head group and (C10H20-O-)n (n = 1, 3, 5, 7) building blocks were attached. The synthetic procedure comprises a series of nucleophilic substitutions under carefully defined conditions. Extended purification is crucial for eliminating non-reacted starting materials.
Key words
self-assembled monolayer (SAM) - organic thiosulfates (Bunte salts) - oligoether - long-chain surfactants - nucleophilic substitution
- 1
Boullanger P.Chevalier Y.Croizier M.-C.Lafont D.Sancho M.-R. Carbohydr. Res. 1995, 278: 91 - 2
Molina L.Papadopoulos D.Selve C. New J. Chem. 1995, 19: 813 - 3
Matsumura Y.Kito M. Surfactant Science Series 2001, 101: 123 - 4
Piispanen PS.Norin T. J. Org. Chem. 2003, 68: 628 - 5
Fitremann J.Bouchu A.Queneau Y. Langmuir 2003, 19: 9981 - 6
Balcom BJ.Petersen NO. Langmuir 1991, 7: 2425 - 7
Laakel N.Rubini P.Rodehuser L. New J. Chem. 1991, 15: 345 - 8
Costes F.Ghoul ME.Bon M.Rico-Lattes I.Lattes A. Langmuir 1995, 11: 3644 - 9
Prata C.More N.Lacombe J.-M.Maurizis J.-C.Pucci B. Carbohydr. Res. 1999, 321: 4 - 10
Satge C.Granet R.Verneuil B.Champavier Y.Krausz P. Carbohydr. Res. 2004, 339: 1243 - 11
Sawada H.Itoh N.Kawase T.Mitani M.Nakajima H.Nishida M.Moriya Y. Langmuir 1994, 10: 994 - 12
Sawada H.Ohashi A.Baba M.Kawase T.Hayakawa Y. J. Fluorine Chem. 1996, 79: 149 - 13
Sawada H.Tanba K.-i.Itoh N.Hosoi C.Oue M.Baba M.Kawase T.Mitani M.Nakajima H. J. Fluorine Chem. 1996, 77: 51 - 14
Sawada H.Kawase T.Ikematsu Y.Ishii Y.Oue M.Hayakawa Y. Chem. Commun. 1996, 886 - 15
Miyamoto M.Aoi K.Saegusa T. Macromolecules 1989, 22: 3540 - 16
Cai Y.Burguiere C.Armes SP. Chem. Commun. 2004, 802 - 17
Pokhrel MR.Bossmann SH. J. Phys. Chem. B 2000, 104: 2215 - 18
Rasheed K. Industrial syntheses of surfactantsLange KR. Carl Hanser Verlag; Munich, Germany: 1999. p.69-130 - 19
Texter J. Reactions and Synthesis in Surfactant Systems Marcel Dekker; New York: 2001. p.1-909 - 20
Katz E.Willner I. In Advanced Macromolecular and Supramolecular Materials and Processes Geckeler, K. E., Ed.; Kluwer Academic/Publishers Plenum; New York: 2003. p.175-196 - 21
Ropers M.-H.Brezesinski G.Mohwald H. Studies in Interface Science Vol. 16 (Organized Monolayers and Assemblies: Structure Processes and Function): Möbius, D.; Miller, R., Eds.; Elsevier; Amsterdam: 2002. p.207-246 - 22
Heinz C.Engelhardt H.Niederweis M. J. Biol. Chem. 2003, 278: 8678 - 23
Gabriel JL.Chong PLG. Chem. Phys. Lipids 2000, 105: 193 - 24
Chong PL.-G.Zein M.Khan TK.Winter R. J. Phys. Chem. B 2003, 107: 8694 - 25
Schuster B.Weigert S.Pum D.Sára M.Sleytr UB. Langmuir 2003, 19: 2392 - 26
Niederweis M.Bossmann SH. Encyclopedia of Nanoscience and Nanotechnology Vol. 7: Nalwa, H. S., Ed.; American Scientific Publishers; Stevenson Ranch, CA, USA: 2004. p.851-867 - 27
Bossmann SH.Janik K.Pokhrel MR.Heinz C.Niederweis M. Surf. Interface Anal. 2004, 36: 127 - 28
Faller M.Niederweis M.Schulz GE. Science 2004, 303: 1189 - 29
Scharf J.Strehblow H.-H.Zeysing B.Terfort A. J. Solid State Electrochem. 2001, 5: 396 - 30
Schönenberger C.Sondag-Huethorst JAM.Jorritsma J.Fokkink LGJ. Langmuir 1994, 10: 611 - 31
Boubour E.Lennox RB. Langmuir 2000, 16: 4222 - 32
Lukkari J.Meretoja M.Kartio I.Laajalehto K.Rajamaeki M.Lindstroem M.Kankare J. Langmuir 1999, 15: 3529 - 33
Distler H. Angew. Chem., Int. Ed. Engl. 1967, 6: 544 - 34
Mumma RO.Fujitani K.Hoiberg CP. J. Chem. Eng. Data 1970, 15: 358 - 35
Naud C.Calas P.Blancou H.Commeyras A. J. Fluorine Chem. 2000, 104: 173 - 36
Shorter J. Nucleophilic Aliphatic Substitution, In Organic Reaction Mechanisms, 2000Knipe AC.Watts WE. John Wiley & Sons; New York: 2004. p.277-306 - 37
Repasky MP.Chandrasekhar J.Jorgensen WL. J. Comput. Chem. 2002, 23: 1601 - 38
Brown WH.Foote CS.Iverson BL. Organic Chemistry Thomson Learning (Brooks Cole); Belmont CA: 2005. p.432-437 - 39
Ackermann J.Videlot C.Nguyen TN.Wang L.Sarro PM.Fages F. Adv. Mater. (Weinheim, Ger.) 2004, 16: 1709 - 40
Teixeira S.Giudici R.Bossmann SH.Lang J.Braun AM. Chem. Eng. Process. 2004, 43: 1317 - 41
Kang SK.Kim WS.Moon BH. Synthesis 1985, 1161 - 42
Duerr H.Kilburg H.Bossmann S. Synthesis 1990, 773 - 43
Bossmann S.Seiler M.Dürr H. J. Phys. Org. Chem. 1992, 5: 63 - 44
Bossmann SH.Dürr H.Pokhrel MR. Synthesis 2005, 907 - 45
Keana JF.Heo GS.Mann JS.Nice FLV.Lex L.Prabhu VS.Ferguson G. J. Org. Chem. 1988, 53: 2268 - 46
Shorter J. Nucleophilic Aliphatic Substitution, In Organic Reaction Mechanisms, 1985Knipe AC.Watts WE. John Wiley & Sons; New York: 1985. p.299-328