Online citations, reference lists, and bibliographies.
← Back to Search

Fluorinated Saccharides On The Si(001) Surface

A. Szwajca, M. Rapp, M. Bilska, M. Krzywiecki, H. Koroniak
Published 2013 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
The attachment of saccharide molecules directly to silicon surface has been for the first time. Oxygen free silicon surface was functionalized with monosacharides thanks to UV irradiation in acetonitryl solution (254 nm). Selected derivatives of pentofuranose were protected at the C-1 and C-2 position. The remaining hydroxyl group at C-3 or C-5 was suitable for direct attachment to H-terminated Si(0 0 1) surface via SiOC bonds. The binding energy of the saccharide to the Si surface was investigated by quantum mechanical calculations method. The Parametric Method 5 (PM5) calculations confirmed that the formation of SiOC bonds was chemically possible. Synthesis of new fluorinated carbohydrates has been described. The resulting monolayers were characterized by Atomic Force Microscopy (AFM), X-ray photoelectron spectroscopy (XPS) and Attenuated Total Reflection (ATR) infrared spectroscopy. The effect of incorporating fluorine atom or CF3 group into self-assembled monosaccharide monolayers was studied using a water contact angle measurements. The resulting surface wettability of different fluorinated components on one kind of planar substrate enables an answer which of derivative is required for the preparation of the hydrophobic monolayer.
This paper references
10.1039/c0cc02105a
Grafted cellulose strands on the surface of silica: effect of environment on reactivity.
O. Gazit (2011)
10.1002/SIA.995
Bioengineered material surfaces for medical applications
H. Mathieu (2001)
10.1021/LA0203685
Preparation of Multilayer Thin Films Containing Avidin through Sugar−Lectin Interactions and Their Binding Properties
T. Hoshi (2002)
10.1016/j.jsb.2011.05.018
Molecular recognition force spectroscopy of a specific lectin-carbohydrate interaction at single-molecule level.
Y. Li (2011)
10.1021/la800066g
Synthesis of carbohydrate-conjugated nanoparticles and quantum dots.
Christopher M. Earhart (2008)
10.1039/b610213c
Fluorine in medicinal chemistry.
Sophie Purser (2008)
10.1063/1.3076115
Toward metal-organic insulator-semiconductor solar cells, based on molecular monolayer self-assembly on n-Si
Rotem Har-lavan (2009)
10.1006/JCIS.1997.4923
Adsorption ofn-Dodecyl-β-d-maltoside on Solids
L. Zhang (1997)
10.1016/S0927-7757(96)03778-8
Synthesis of new sugar-based surfactants having biological applications: key role of their self-association
I. Rico-Lattes (1997)
10.1016/S0008-6215(00)83838-0
A simple preparation of 2-(acylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-d-glucose dimethyl and dibenzyl acetal
A. Hasegawa (1980)
10.1007/b100331
Electrochemistry of silicon and its oxide
X. Zhang (2001)
10.1039/CS9871600381
Modern methods for the introduction of fluorine into organic molecules: an approach to compounds with altered chemical and biological activities
J. Mann (1987)
10.1021/JO00065A025
Chemoselective hydrolysis of terminal isopropylidene acetals and subsequent glycol cleavage by periodic acid in one pot
W. Wu (1993)
10.1016/J.BIOS.2004.10.006
Study of real-time lectin-carbohydrate interactions on the surface of a quartz crystal microbalance.
Zhichao Pei (2005)
10.1021/BM015648Y
Heterogeneity in bacterial surface polysaccharides, probed on a single-molecule basis.
T. Camesano (2002)
10.1039/P298700000S1
Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds
F. Allen (1987)
10.1021/JA00116A019
Alkyl Monolayers on Silicon Prepared from 1-Alkenes and Hydrogen-Terminated Silicon
M. R. Linford (1995)
10.1016/J.JFLUCHEM.2011.07.001
Fluorination of tertiary alcohols derived from di-O-isopropylidenehexofuranose and O-isopropylidenepentofuranose
M. Rapp (2011)
10.1002/JMR.826
A survey of the 2001 to 2005 quartz crystal microbalance biosensor literature: applications of acoustic physics to the analysis of biomolecular interactions
M. Cooper (2007)
10.1016/S0040-4020(01)90286-8
Tetrahedron report number 221
J. Welch (1987)
10.1080/10610270802527010
FT-IR, semi-empirical and electrochemical studies of lasalocid ester with 2, 2′-dithiodiethanol adsorbed on silver surface
R. Pankiewicz (2009)
10.1021/LA0349020
Patterned adsorption of protein onto a carbohydrate monolayer immobilized on Si
Naoto Shirahata (2003)
10.1002/SIA.740060302
AES: Energy calibration of electron spectrometers. I—an absolute, traceable energy calibration and the provision of atomic reference line energies
M. P. Seah (1984)
10.1016/J.TSF.2007.04.061
The self-assembled monolayer of saccharide via click chemistry: Formation and protein recognition
Y. Miura (2008)
10.1002/9780470281895
Bioorganic and Medicinal Chemistry of Fluorine
Jean-Pierre Bégué (2008)
10.1021/ja901831u
Mesoporous silica nanoparticle-based double drug delivery system for glucose-responsive controlled release of insulin and cyclic AMP.
Yannan Zhao (2009)
10.1021/JA037445I
Covalently attached saccharides on silicon surfaces.
L. C. P. M. de Smet (2003)
10.1016/S0022-1139(98)00300-5
Synthesis and characterization of perfuoropolyethers from perfluoromethylvinylether
G. Marchionni (1999)
10.1021/bc900110x
Photoinitiated coupling of unmodified monosaccharides to iron oxide nanoparticles for sensing proteins and bacteria.
L. Liu (2009)
10.1016/J.JCIS.2007.07.058
Dewetting and surface properties of ultrathin films of cellulose esters.
P. Kosaka (2007)
10.1021/JA00055A034
Origin of the stability of carbon tetrafluoride: negative hyperconjugation reexamined
K. Wiberg (1993)
10.1021/JO9705428
Effect of Fluorination on the Conformational Properties of Methyl Vinyl Ether
C. Leibold (1997)
10.1016/J.CARRES.2004.09.004
Syntheses of alkenylated carbohydrate derivatives toward the preparation of monolayers on silicon surfaces.
L. C. P. M. de Smet (2004)
10.1002/jps.22481
Silica-maltose composites: obtaining drug carrier systems through tailored ultrastructural nanoparticles.
G. D. Leirose (2011)
10.1016/J.JFLUCHEM.2006.07.006
1,1,3,3,3-Pentafluoropropene secondary amine adducts new selective fluorinating agents
H. Koroniak (2006)
10.1007/978-3-642-18865-7
Semiconductors: Data Handbook
O. Madelung (2003)
10.1002/chem.201103422
Rapid preparation of multifunctional surfaces for orthogonal ligation by microcontact chemistry.
Christian Wendeln (2012)
10.1021/la201324h
Polymer-based photocoupling agent for the efficient immobilization of nanomaterials and small molecules.
T. Kubo (2011)
10.1021/JA054811K
Fluorous-based carbohydrate microarrays.
K. Ko (2005)
10.1021/LA9904962
An Improved Method for the Preparation of Organic Monolayers of 1-Alkenes on Hydrogen-Terminated Silicon Surfaces
A. Sieval (1999)
10.1016/S0008-6215(00)00030-6
Preparation of fluorine-18 labelled sugars and derivatives and their application as tracer for positron-emission-tomography.
B. Beuthien-Baumann (2000)
10.1021/bm8005402
Functionalization of magnetic nanowires by charged biopolymers.
D. Magnin (2008)
10.1080/07328319708006168
Gemcitabine: Actions and Interactions
W. Plunkett (1997)
10.1016/S0003-2697(02)00318-4
Self-assembled monolayers of globotriaosylceramide (Gb3) mimics: surface-specific affinity with shiga toxins.
Y. Miura (2002)
10.1021/la903569v
Carbohydrate microarrays by microcontact printing.
Christian Wendeln (2010)
10.1016/S0008-6215(00)00012-4
Carbohydrate- and related polyol-derived fluorosurfactants: an update.
J. Riess (2000)
10.1021/JO960355U
EFFICIENT DEHOMOLOGATION OF DI-O-ISOPROPYLIDENEHEXOFURANOSE DERIVATIVES TO GIVE O-ISOPROPYLIDENEPENTOFURANOSES BY SEQUENTIAL TREATMENT WITH PERIODIC ACID IN ETHYL ACETATE AND SODIUM BOROHYDRIDE
M. Xie (1996)
10.1039/b909363j
Silica-based clicked hybrid glyco materials.
F. Santoyo-González (2009)
10.1016/S0008-6215(00)85502-0
Synthesis of 1,2-O-isopropylidence-α-d-ribofuranose from d-ribose
H. Tsutsumi (1979)
10.1016/j.bpj.2009.05.053
Micellar and biochemical properties of (hemi)fluorinated surfactants are controlled by the size of the polar head.
C. Breyton (2009)
10.1016/J.JFLUCHEM.2006.01.001
Noncovalent fluorous interactions for the synthesis of carbohydrate microarrays
S. Mamidyala (2006)
10.1107/S0567740880008382
Straight Si–O–Si bridging bonds do exist in silicates and silicon dioxide polymorphs
W. Baur (1980)
10.1002/POLA.23075
Polymer Brushes Containing Sulfonated Sugar Repeat Units: Synthesis, Characterization and In Vitro Testing of Blood Coagulation Activation.
N. Ayres (2008)
10.1039/b711844a
Understanding organofluorine chemistry. An introduction to the C-F bond.
D. O'Hagan (2008)
10.1021/bc9003519
Photo-click immobilization of carbohydrates on polymeric surfaces--a quick method to functionalize surfaces for biomolecular recognition studies.
Oscar Norberg (2009)
10.1016/j.colsurfb.2012.01.002
Facile construction of functional biosurface via SI-ATRP and "click glycosylation".
W. Song (2012)
10.1021/bc100251f
A universal protocol for photochemical covalent immobilization of intact carbohydrates for the preparation of carbohydrate microarrays.
H. Wang (2011)
10.1021/BI0484623
A piezoelectric quartz crystal biosensor: the use of two single cysteine mutants of the periplasmic Escherichia coli glucose/galactose receptor as target proteins for the detection of glucose.
K. Carmon (2004)
10.1016/S0008-6215(00)83749-0
Oxidation of primary and secondary alcohols in partially protected sugars with the chromium trioxide-pyridine complex in the presence of acetic anhydride
P. Garegg (1978)



This paper is referenced by
10.1016/J.JFLUCHEM.2015.10.009
Self-assembled monolayers of partially fluorinated alcohols on Si(001): XPS and UV-photoemission study
A. Szwajca (2015)
10.1016/J.PORGCOAT.2019.04.078
A novel hydrophobic coating film of water-borne fluoro-silicon polyacrylate polyurethane with properties governed by surface self-segregation
Zhou Yi (2019)
10.1021/MA501828W
Iodine Transfer Copolymerization of Fluorinated α-Methylstyrenes with Styrene Using 1-Iodoperfluorohexane as the Chain Transfer Agent
Justyna Walkowiak-Kulikowska (2014)
10.1016/J.JFLUCHEM.2014.06.013
A convenient synthesis of fluorinated vinyl ethers derived from di-O-isopropylidenehexofuranose and O-isopropylidenepentofuranose
B. Marciniak (2014)
10.1016/j.jfluchem.2019.109364
Design, properties and applications of fluorinated and fluoroalkylated N-containing monosaccharides and their analogues
Monika Bilska-Markowska (2019)
10.1016/J.JFLUCHEM.2017.09.005
Preparation of chiral sugar-derived fluorides using new nucleophilic fluorinating reagents
Monika Bilska-Markowska (2017)
10.1016/J.APSUSC.2013.07.156
Synthesis and properties of a novel UV-cured fluorinated siloxane graft copolymer for improved surface, dielectric and tribological properties of epoxy acrylate coating
Zhenlong Yan (2013)
10.1016/J.JFLUCHEM.2014.07.016
Encapsulation of fluoroaromatics by β-cyclodextrin and their derivatives theoretical studies
A. Szwajca (2014)
10.1080/10426507.2015.1100190
Fluorinated SAMs on Si(001) surface: Surface electronic properties and structural aspects
A. Szwajca (2016)
10.1002/SLCT.201800149
3D‐Ordered Mesoporous Chromium‐Doped Titania Thin Films: The Effect of Metal Dopant on the Microstructure, Mesoporous Symmetry, Hydrophobicity, and Surface Properties
A. Imani (2018)
Semantic Scholar Logo Some data provided by SemanticScholar