title: Saccharide-functionalized alkanethiols for fouling-resistant self-assembled monolayers: synthesis, monolayer properties, and antifouling behavior.
abstract: We describe the synthesis of a series of mono-, di-, and trisaccharide-functionalized alkanethiols as well as the formation of fouling-resistant self-assembled monolayers (SAMs) from these. The SAMs were characterized using ellipsometry, wetting measurements, and infrared reflection-absorption spectroscopy (IRAS). We show that the structure of the carbohydrate moiety affects the packing density and that this also alters the alkane chain organization. Upon increasing the size of the sugar moieties (from mono- to di- and trisaccharides), the structural qualities of the monolayers deteriorated with increasing disorder, and for the trisaccharide, slow reorganization dynamics in response to changes in the environmental polarity were observed. The antifouling properties of these SAMs were investigated through protein adsorption experiments from buffer solutions as well as settlement (attachment) tests using two common marine fouling species, zoospores of the green macroalga Ulva linza and cypris larvae of the barnacle Balanus amphitrite. The SAMs showed overall good resistance to fouling by both the proteins and the tested marine organisms. To improve the packing density of the SAMs with bulky headgroups, we employed mixed SAMs where the saccharide-thiols are diluted with a filler molecule having a small 2-hydroxyethyl headgroup. This method also provides a means by which the steric availability of sugar moieties can be varied, which is of interest for specific interaction studies with surface-bound sugars. The results of the surface dilution study and the low nonspecific adsorption onto the SAMs both indicate the feasibility of this approach.
authors: Division of Chemistry, IFM, Linköping University, SE-581 83 Linköping, Sweden.
authors: Timmy
authors: T
authors: Fyrner
authors: Hung-Hsun
authors: HH
authors: Lee
authors: Alberto
authors: A
authors: Mangone
authors: Tobias
authors: T
authors: Ekblad
authors: Michala E
authors: ME
authors: Pettitt
authors: Maureen E
authors: ME
authors: Callow
authors: James A
authors: JA
authors: Callow
authors: Sheelagh L
authors: SL
authors: Conlan
authors: Robert
authors: R
authors: Mutton
authors: Anthony S
authors: AS
authors: Clare
authors: Peter
authors: P
authors: Konradsson
authors: Bo
authors: B
authors: Liedberg
authors: Thomas
authors: T
authors: Ederth
mesh_terms: D000327:Adsorption; D000473:Alkanes / Q000737:chemistry; D000818:Animals; D001665:Binding Sites; D004202:Disinfectants / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D009005:Monosaccharides / Q000737:chemistry*; D009844:Oligosaccharides / Q000737:chemistry*; D011485:Protein Binding / Q000187:drug effects; D011506:Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D012031:Refractometry; D013055:Spectrophotometry, Infrared; D013057:Spectrum Analysis; D013170:Spores / Q000187:drug effects* / Q000254:growth & development; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D001468:Thoracica / Q000187:drug effects* / Q000502:physiology; D044445:Ulva / Q000187:drug effects / Q000254:growth & development; D017155:Wettability
chemical_list: D000473:Alkanes; D004202:Disinfectants; D009005:Monosaccharides; D009844:Oligosaccharides; D011506:Proteins; D013438:Sulfhydryl Compounds