Abstract
6 -Cysteinyl amino methylated β-cyclodextrin was adsorbed on Au(111) as well as on mercury electrode. Scanning probe microscopy and electrochemical techniques confirmed that a chemisorbed self-assembled monolayer (SAM) of the β-cyclodextrin is formed, proving that a single –SH moiety located in the cysteinyl group is sufficient to anchor the entire methylated β-cyclodextrin molecule to the electrode surface. Thus, formed SAM can potentially serve as sensor layer for various organic molecules such as pesticides, antibiotics, and optically active compounds.
Graphical abstract
Similar content being viewed by others
References
Rekharsky MV, Inoue Y (1998) Chem Rev 98:1875
Hapiot F, Tilloy S, Monflier E (2006) Chem Rev 106:767
Hromadová M, Sokolová R (2011) Curr Org Chem 15:2950
Siegel B, Breslow R (1975) J Am Chem Soc 97:6869
Kolivoška V, Gál M, Hromadová M, Valášek M, Pospíšil L (2011) J Organomet Chem 696:1404
Viernstein H, Reiter S, Wolschann P (1994) Monatsh Chem 125:681
Pospíšil L, Trsková R, Colombini MP, Fuoco R (1998) J Incl Phenom 31:57
Shehatta I (2002) Monatsh Chem 133:1239
Ramešová Š, Sokolová R, Degano I, Hromadová M, Gál M, Kolivoška V, Colombini MP (2011) Collect Czech Chem Commun 76:1651
Hromadová M, Kolivoška V, Gál M, Pospíšil L, Sokolová R, Valášek M (2011) J Incl Phenom 70:461
Pospíšil L, Hromadová M, Gál M, Bulíčková J, Sokolová R, Fanelli N (2008) Electrochim Acta 53:7445
Buschmann HJ, Schollmeyer E (2002) J Cosmet Sci 53:185
Loftsson T, Jarho P, Másson M, Järvinen T (2005) Expert Opin Drug Deliv 2:335
Beulen MWJ, Bugler J, de Jong MR, Lammerink B, Huskens J, Schönherr H, Vancso GJ, Boukamp BA, Wieder H, Offenhauser A, Knoll W, van Veggel FCJM, Reinhoudt DN (2000) Chem Eur J 6:1176
Zapotoczny S, Auletta T, de Jong MR, Schönherr H, Huskens J, van Veggel FCJM, Reinhoudt DN, Vancso GJ (2002) Langmuir 18:6988
Schönherr H, Beulen MWJ, Bugler J, Huskens J, van Veggel FCJM, Reinhoudt DN, Vancso GJ (2000) J Am Chem Soc 122:4963
Rojas MT, Kiiniger R, Stoddart JF, Kaifer AE (1995) J Am Chem Soc 117:336
Domi Y, Yoshinaga Y, Shimazu K, Porter MD (2009) Langmuir 25:8094
Kolivoška V, Mohos M, Pobelov IV, Rohrbach S, Yoshida K, Hong WJ, Fu YC, Moreno-Garcia P, Mészáros G, Broekmann P, Hromadová M, Sokolová R, Valášek M, Wandlowski T (2014) Chem Comm 50:11757
Méndez-Ardoy A, Steentjes T, Kudernac T, Huskens J (2014) Langmuir 30:3467
Loukou C, Changenet-Barret P, Rager MN, Plaza P, Martin MM, Mallet JM (2011) Org Biomol Chem 9:2209
Binnig G, Rohrer H (1986) IBM J Res Dev 30:355
Chiang S (2011) J Phys D Appl Phys 44:464001
Colton RJ, Engel A, Frommer JE, Gaub HE, Gewirth AA, Guckenberger R, Rabe J, Heckl WM, Parkinson B (1998) Procedures in scanning probe microscopy. Wiley, London
Schönenberger C, Sondag-Huethorst JAM, Jorritsma J, Fokking LGJ (1994) Langmuir 10:611
Van Patten PG, Noll JD, Myrick ML (1997) J Phys Chem B 101:7874
Korayem MH, Kavousi A, Ebrahimi N (2011) Sci Iran 18:121
Liu GY, Xu S (2009) Nanometer scale fabrication of self-assembled monolayers: nanoshaving and nanografting. In: Winter CH, Hofman DM (eds) Inorganic materials synthesis, vol 727. American Chemical Society, Washington, p 199
Kolivoška V, Gál M, Hromadová M, Lachmanová Š, Tarábková H, Janda P, Pospíšil L, Turoňová AM (2012) Colloids Surf B 94:213
Kolivoška V, Gál M, Lachmanová Š, Janda P, Sokolová R, Hromadová M (2011) Coll Czech Chem Commun 76:1075
Bard AJ, Faulkner LR (2001) Electrochemical methods: fundamentals and applications. Wiley, New York
Gorman CB, Biebuyck HA, Whitesides GM (1995) Langmuir 11:2242
Pensa E, Vericat C, Grumelli D, Salvarezza RC, Park SH, Longo GS, Szleifer I, De Leo LPM (2012) Phys Chem Chem Phys 14:12355
Lee LYS, Lennox RB (2007) Langmuir 23:292
Hromadová M, Kolivoška V, Sokolová R, Gál M, Pospíšil L, Valášek M (2010) Langmuir 26:17232
Acknowledgments
VK thanks for the financial support from Sciex (10.209) as well as Academy of Sciences of the Czech Republic (L200401501). Grant Agency of the Czech Republic is greatly acknowledged (14-05180S) by MH. Financial support from the French National Research Agency (ANR BLAN femtomotile) to CL and JMM is acknowledged.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Rights and permissions
About this article
Cite this article
Kolivoška, V., Sokolová, R., Kocábová, J. et al. Formation and investigation of 6-cysteinyl amino methylated β-cyclodextrin self-assembled monolayers. Monatsh Chem 147, 45–51 (2016). https://doi.org/10.1007/s00706-015-1609-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-015-1609-2