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 (C10 H20 -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
References
<A NAME="RM02905SS-1">1 </A>
Boullanger P.
Chevalier Y.
Croizier M.-C.
Lafont D.
Sancho M.-R.
Carbohydr. Res.
1995,
278:
91
<A NAME="RM02905SS-2">2 </A>
Molina L.
Papadopoulos D.
Selve C.
New J. Chem.
1995,
19:
813
<A NAME="RM02905SS-3">3 </A>
Matsumura Y.
Kito M.
Surfactant Science Series
2001,
101:
123
<A NAME="RM02905SS-4">4 </A>
Piispanen PS.
Norin T.
J. Org. Chem.
2003,
68:
628
<A NAME="RM02905SS-5">5 </A>
Fitremann J.
Bouchu A.
Queneau Y.
Langmuir
2003,
19:
9981
<A NAME="RM02905SS-6">6 </A>
Balcom BJ.
Petersen NO.
Langmuir
1991,
7:
2425
<A NAME="RM02905SS-7">7 </A>
Laakel N.
Rubini P.
Rodehuser L.
New J. Chem.
1991,
15:
345
<A NAME="RM02905SS-8">8 </A>
Costes F.
Ghoul ME.
Bon M.
Rico-Lattes I.
Lattes A.
Langmuir
1995,
11:
3644
<A NAME="RM02905SS-9">9 </A>
Prata C.
More N.
Lacombe J.-M.
Maurizis J.-C.
Pucci B.
Carbohydr. Res.
1999,
321:
4
<A NAME="RM02905SS-10">10 </A>
Satge C.
Granet R.
Verneuil B.
Champavier Y.
Krausz P.
Carbohydr. Res.
2004,
339:
1243
<A NAME="RM02905SS-11">11 </A>
Sawada H.
Itoh N.
Kawase T.
Mitani M.
Nakajima H.
Nishida M.
Moriya Y.
Langmuir
1994,
10:
994
<A NAME="RM02905SS-12">12 </A>
Sawada H.
Ohashi A.
Baba M.
Kawase T.
Hayakawa Y.
J. Fluorine Chem.
1996,
79:
149
<A NAME="RM02905SS-13">13 </A>
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
<A NAME="RM02905SS-14">14 </A>
Sawada H.
Kawase T.
Ikematsu Y.
Ishii Y.
Oue M.
Hayakawa Y.
Chem. Commun.
1996,
886
<A NAME="RM02905SS-15">15 </A>
Miyamoto M.
Aoi K.
Saegusa T.
Macromolecules
1989,
22:
3540
<A NAME="RM02905SS-16">16 </A>
Cai Y.
Burguiere C.
Armes SP.
Chem. Commun.
2004,
802
<A NAME="RM02905SS-17">17 </A>
Pokhrel MR.
Bossmann SH.
J. Phys. Chem. B
2000,
104:
2215
<A NAME="RM02905SS-18">18 </A>
Rasheed K.
Industrial syntheses of surfactants
Lange KR.
Carl Hanser Verlag;
Munich, Germany:
1999.
p.69-130
<A NAME="RM02905SS-19">19 </A>
Texter J.
Reactions and Synthesis in Surfactant Systems
Marcel Dekker;
New York:
2001.
p.1-909
<A NAME="RM02905SS-20">20 </A>
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
<A NAME="RM02905SS-21">21 </A>
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
<A NAME="RM02905SS-22">22 </A>
Heinz C.
Engelhardt H.
Niederweis M.
J. Biol. Chem.
2003,
278:
8678
<A NAME="RM02905SS-23">23 </A>
Gabriel JL.
Chong PLG.
Chem. Phys. Lipids
2000,
105:
193
<A NAME="RM02905SS-24">24 </A>
Chong PL.-G.
Zein M.
Khan TK.
Winter R.
J. Phys. Chem. B
2003,
107:
8694
<A NAME="RM02905SS-25">25 </A>
Schuster B.
Weigert S.
Pum D.
Sára M.
Sleytr UB.
Langmuir
2003,
19:
2392
<A NAME="RM02905SS-26">26 </A>
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
<A NAME="RM02905SS-27">27 </A>
Bossmann SH.
Janik K.
Pokhrel MR.
Heinz C.
Niederweis M.
Surf. Interface Anal.
2004,
36:
127
<A NAME="RM02905SS-28">28 </A>
Faller M.
Niederweis M.
Schulz GE.
Science
2004,
303:
1189
<A NAME="RM02905SS-29">29 </A>
Scharf J.
Strehblow H.-H.
Zeysing B.
Terfort A.
J. Solid State Electrochem.
2001,
5:
396
<A NAME="RM02905SS-30">30 </A>
Schönenberger C.
Sondag-Huethorst JAM.
Jorritsma J.
Fokkink LGJ.
Langmuir
1994,
10:
611
<A NAME="RM02905SS-31">31 </A>
Boubour E.
Lennox RB.
Langmuir
2000,
16:
4222
<A NAME="RM02905SS-32">32 </A>
Lukkari J.
Meretoja M.
Kartio I.
Laajalehto K.
Rajamaeki M.
Lindstroem M.
Kankare J.
Langmuir
1999,
15:
3529
<A NAME="RM02905SS-33">33 </A>
Distler H.
Angew. Chem., Int. Ed. Engl.
1967,
6:
544
<A NAME="RM02905SS-34">34 </A>
Mumma RO.
Fujitani K.
Hoiberg CP.
J. Chem. Eng. Data
1970,
15:
358
<A NAME="RM02905SS-35">35 </A>
Naud C.
Calas P.
Blancou H.
Commeyras A.
J. Fluorine Chem.
2000,
104:
173
<A NAME="RM02905SS-36">36 </A>
Shorter J.
Nucleophilic Aliphatic Substitution , In Organic Reaction Mechanisms, 2000
Knipe AC.
Watts WE.
John Wiley & Sons;
New York:
2004.
p.277-306
<A NAME="RM02905SS-37">37 </A>
Repasky MP.
Chandrasekhar J.
Jorgensen WL.
J. Comput. Chem.
2002,
23:
1601
<A NAME="RM02905SS-38">38 </A>
Brown WH.
Foote CS.
Iverson BL.
Organic Chemistry
Thomson Learning (Brooks Cole);
Belmont CA:
2005.
p.432-437
<A NAME="RM02905SS-39">39 </A>
Ackermann J.
Videlot C.
Nguyen TN.
Wang L.
Sarro PM.
Fages F.
Adv. Mater. (Weinheim, Ger.)
2004,
16:
1709
<A NAME="RM02905SS-40">40 </A>
Teixeira S.
Giudici R.
Bossmann SH.
Lang J.
Braun AM.
Chem. Eng. Process.
2004,
43:
1317
<A NAME="RM02905SS-41">41 </A>
Kang SK.
Kim WS.
Moon BH.
Synthesis
1985,
1161
<A NAME="RM02905SS-42">42 </A>
Duerr H.
Kilburg H.
Bossmann S.
Synthesis
1990,
773
<A NAME="RM02905SS-43">43 </A>
Bossmann S.
Seiler M.
Dürr H.
J. Phys. Org. Chem.
1992,
5:
63
<A NAME="RM02905SS-44">44 </A>
Bossmann SH.
Dürr H.
Pokhrel MR.
Synthesis
2005,
907
<A NAME="RM02905SS-45">45 </A>
Keana JF.
Heo GS.
Mann JS.
Nice FLV.
Lex L.
Prabhu VS.
Ferguson G.
J. Org. Chem.
1988,
53:
2268
<A NAME="RM02905SS-46">46 </A>
Shorter J.
Nucleophilic Aliphatic Substitution , In Organic Reaction Mechanisms, 1985
Knipe AC.
Watts WE.
John Wiley & Sons;
New York:
1985.
p.299-328