A convenient synthesis of long-chain 4-substituted benzyloxycarbonyl alkanethiols for the formation of self assembled monolayers on metal substrates

• Authors: Polina Angelova , Kalina Kostova , Karsten Hinrichs , Dimiter Tsankov
• Languages of publication: EN

Abstracts

EN

New 4-substituted benzyl esters of 16-mercaptohexadecanoic acid were prepared by developing a practicable synthetic procedure and using readily available staring materials. The compounds synthesized have been characterized by NMR, MS, IR spectra and elemental analysis. The mercapto derivatives are precursors for the formation of self-assembled monolayers on metal substrates.

Keywords

EN

Alkanethiols; hexadecanoic acid; esterification; N-acylurea; self-assembled monolayers (SAM)

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2005
• Volume: 3
• Issue: 4
• Pages: 658-667

Dates

published

1 - 12 - 2005

online

1 - 12 - 2005

Contributors

author

Polina Angelova

• Institute of Organic Chemistry, Bulgarian Academy of Sciences, Akad. G. Bonchev Str. Bl. 9, 1113, Sofia, Bulgaria

author

Kalina Kostova

• Institute of Organic Chemistry, Bulgarian Academy of Sciences, Akad. G. Bonchev Str. Bl. 9, 1113, Sofia, Bulgaria

author

Karsten Hinrichs

• Department Berlin, ISAS-Institute for Analytical Sciences, Albert Einstein Str. 9, 12489, Berlin, Germany

author

Dimiter Tsankov

• Institute of Organic Chemistry, Bulgarian Academy of Sciences, Akad. G. Bonchev Str. Bl. 9, 1113, Sofia, Bulgaria

References

• [1] A. Ulman: An Introduction to Ultrathin Organic Films: From Langmuir-Blodgett to Self-Assembly, Academic Press, San Diego, 1991.
• [2] D. Roy and J. Fendler: “Reflection and absorption techniques for optical characterization of chemically assembled materials”, Adv. Mater., Vol. 16, (2004). pp. 479–508. http://dx.doi.org/10.1002/adma.200306195[Crossref]
• [3] R. Smith, P.A. Lewis and P.S. Weiss: “Patterning self-assembled monolayers”, Progr. Surf. Sci.. Vol. 75, (2004), pp. 1–68. http://dx.doi.org/10.1016/j.progsurf.2003.12.001[Crossref]
• [4] K.E. Nelson, L. Gamble, L.S. Jung, M.S. Boeckl, E. Naeemi, S.L. Golledge, T. Sasaki, D.G. Castner, C.T. Campbell and P. Stayton: “Surface Characterization of Mixed self-Assembled Monolayers Designed for Streptavidin Immobilization”, Langmiur, Vol. 17, (2001), pp. 2807–2816. http://dx.doi.org/10.1021/la010456+[Crossref]
• [5] J. Chen, J. Su, W. Wang and M.A. Reed: “Electronic memory effects in self-assembled monolayer systems”, Physica-E. Vol. 16, (2003), pp. 17–23. http://dx.doi.org/10.1016/S1386-9477(02)00577-5[Crossref]
• [6] M. Watanabe and K. Kajikawa: “An optical fiber biosensor based on anomalous reflection of gold”, Sens. Actuators. Vol. 89, (2003), pp. 126–130. http://dx.doi.org/10.1016/S0925-4005(02)00453-7[Crossref]
• [7] M. Alvarez, A. Calle, J. Tamayo, L.M. Lechuga, A. Abad and A. Montoya: “Development of nanomechanical biosensors for detection of the pesticide DDT”, Biosens. Bioelectron.. Vol. 18, (2003), pp. 649–653. http://dx.doi.org/10.1016/S0956-5663(03)00035-6[Crossref]
• [8] L.A. Bumm, J.J. Arnold, M.T. Cygan, T.D. Dunbar, T.P. Burgin, L. Jones, D.L. Allara, J.M. Tour and P.S. Weiss: “Are single molecular wires conducting?”, Science, Vol. 271, (1996), pp. 1705–1707. [Crossref]
• [9] M. Zharnikov and M. Grunze: “Spectroscopic characterization of thiol-derived selfassembling monolayer”, J. Phys.: Condens. Matter. Vol. 13, (2001), pp. 11333–11365. http://dx.doi.org/10.1088/0953-8984/13/49/314[Crossref]
• [10] For recent review see J.C. Love, L.A. Estroff, J.K. Kriebel, R.G. Nuzzo and G.M. Whitesides: “Self-Assambled Monolayers of Thiolates on Metals as a Form of Nanotechnology”, Chem. Rev.. Vol. 105, (2005), pp. 1103–1169. http://dx.doi.org/10.1021/cr0300789[Crossref]
• [11] F. Buckel, P. Persson and F. Effenberger: “Synthesis of Functionalized Long-Chain Thiols and Thiophenols for the Formation of Self-Assembled Monolayers on Gold”, Synthesis, (1999), pp. 953–958 and references cited therein.
• [12] J. Lahann, S. Mitragotri, T.-N. Tran, H. Kaido, J. Sundaram, I.S. Choi, S. Hoffer, G.A. Somorjai and R. Langer: “A Reversibly Switching Surface”, Science. Vol. 299, (2003), pp. 371–374. http://dx.doi.org/10.1126/science.1078933[Crossref]
• [13] S.J. Stranick, A.N. Parikh, Y.-T. Tao, D.L. Allara and P.S. Weiss: “Phase Separation of Mixed-Composition Self-Assembled Monolayers into Nanometer Scale Molecular Domains”, J. Phys. Chem.. Vol. 98, (1994), pp. 7636–7646. http://dx.doi.org/10.1021/j100082a040[Crossref]
• [14] J.-B.D. Green, M.T. McDermott and M.D. Porter: “Phase Separation of Mixed-Composition Self-Assembled Monolayers into Nanometer Scale Molecular Force Microscopy”, J. Phys. Chem.. Vol. 99, (1995), pp. 10960–10965. http://dx.doi.org/10.1021/j100027a041[Crossref]
• [15] S. Svedhem, C.-A. Hollander, J. Shi, P. Konradsson, B. Liedberg and S.C.T. Svensson: “Synthesis of Series of Oligo (ethylene glycol)-Terminated Alkanethiol Amides Designed to Address Structure and Stability of Biosensing Interfaces”, J. Org. Chem., Vol. 66, (2001), pp. 4494–4503. http://dx.doi.org/10.1021/jo0012290[Crossref]
• [16] R. Valiokas, S. Svedhem, M. Östblom, S.C.T. Svensson and B. Liedberg: “Influence of Specific Intermolecular Interactions on the Self-Assambly and Phase Behavior of Oligo (Ethylene Glycol)-Terminated Alkanethiolates on Gold”, J. Phys. Chem. B. Vol. 105, (2001), pp. 5459–5469. http://dx.doi.org/10.1021/jp004441g[Crossref]
• [17] R. Valiokas, M. Östblom, S. Svedhem, S.C.T. Svensson and B. Liedberg: “Therminal Stability of Self-Assembled Monolayers: Influence of Lateral Hydrogen Bonding”, J. Phys. Chem. B.. Vol. 106, (2002), pp. 10401–10409. http://dx.doi.org/10.1021/jp0200526[Crossref]
• [18] D. Fitzmaurice, S.N. Rao, J.A. Preece, J.F. Stoddart, S. Wenger and N. Zaccheroni: “Heterosupramolecular Chemistry: Programmed Pseudorotaxane Assembly at the Surface of a Nanocrystal”, Angew. Chem. Int. Ed.. Vol. 38, (1999), pp. 1147–1150. http://dx.doi.org/10.1002/(SICI)1521-3773(19990419)38:8<1147::AID-ANIE1147>3.0.CO;2-A[Crossref]
• [19] E.P. Boden and G.E. Kecks: “Proton-Transfer Steps in Steglich Esterification: A Very Practical New Method for Macrolactonization”, J. Org. Chem.. Vol. 50, (1985), pp. 2349–2395. http://dx.doi.org/10.1021/jo00213a044[Crossref]
• [20] A. Hassner and V. Alexanian: “Direct Room Temperature Esterification of Carboxylic Acids”, Tetrahedron Lett.. Vol. 46 (1978), pp. 4475–4478. http://dx.doi.org/10.1016/S0040-4039(01)95256-6[Crossref]
• [21] F.E. Ziegler and G.D. Berger: “A Mild Method for the Esterification of Fatty Acids”, Synthetic Commun.. Vol. 9, (1979), pp. 539–543. [Crossref]
• [22] K. Kishikawa, W. Sankhavasi and M. Yamamoto: “A Two-Step Synthesis of (±)-Blastmycinolactol using Acylurea”, Synthetic Commun., Vol. 20, (1990), pp. 2339–2347, [Crossref]
• [23] M. Kaŝemëkaitë, A. Bulovas, V. Smirnovas, G. Niaure, E. Butkus and V. Razumas: “Synthesis of new SAM-forming ferrocene derivatives and their interfacial properties on gold”, Tetrahedron Lett.. Vol. 42, (2001), pp. 7691–7694. http://dx.doi.org/10.1016/S0040-4039(01)01625-2[Crossref]

Identifiers

DOI

10.2478/BF02475194