Molecular printboards on silicon oxide: lithographic patterning of cyclodextrin monolayers with multivalent, fluorescent guest molecules.
Three compounds bearing multiple adamantyl guest moieties and a fluorescent dye have been synthesized for the supramolecular patterning of beta-cyclodextrin (CD) host monolayers on silicon oxide using microcontact printing and dip-pen nanolithography. Patterns created on monolayers on glass were viewed by laser scanning confocal microscopy. Semi-quantitative analysis of the patterns showed that with microcontact printing approximately a single monolayer of guest molecules is transferred. Exposure to different rinsing procedures showed the stability of the patterns to be governed by specific supramolecular multivalent interactions. Patterns of the guest molecules created at CD monolayers were stable towards thorough rinsing with water, whereas similar patterns created on poly(ethylene glycol) (PEG) reference monolayers were instantly removed. The patterns on CD monolayers displayed long-term stability when stored under N(2), whereas patterns at PEG monolayers faded within a few weeks due to the diffusion of fluorescent molecules across the surface. Assemblies at CD monolayers could be mostly removed by rinsing with a concentrated CD solution, demonstrating the reversibility of the methodology. Patterns consisting of different guest molecules were produced by microcontact printing of one guest molecule and specific adsorption of a second guest molecule from solution to non-contacted areas, giving well-defined alternating assemblies. Fluorescent features of sub-micrometer dimensions were written using supramolecular dip-pen nanolithography.
Mulder
Alart
A
Laboratory of Supramolecular Chemistry and Technology, MESA+ Institute for Nanotechnology, University of Twente, P. O. Box 217, 7500 AE Enschede, The Netherlands.
Onclin
Steffen
S
Péter
Mária
M
Hoogenboom
Jacob P
JP
Beijleveld
Hans
H
ter Maat
Jurjen
J
García-Parajó
María F
MF
Ravoo
Bart Jan
BJ
Huskens
Jurriaan
J
van Hulst
Niek F
NF
Reinhoudt
David N
DN
D000181:Acrylonitrile / Q000737:chemistry; D003505:Cyclodextrins / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000494:pharmacology; D007281:Ink; D007834:Lasers; D009682:Magnetic Resonance Spectroscopy; D008752:Methylene Chloride / Q000737:chemistry; D018613:Microscopy, Confocal; D008956:Models, Chemical; D049329:Nanostructures / Q000737:chemistry; D036103:Nanotechnology / Q000379:methods*; D011092:Polyethylene Glycols / Q000737:chemistry; D012822:Silicon Dioxide / Q000737:chemistry*; D013053:Spectrophotometry / Q000379:methods; D047392:beta-Cyclodextrins / Q000737:chemistry
D003505:Cyclodextrins; D005456:Fluorescent Dyes; D047392:beta-Cyclodextrins; D011092:Polyethylene Glycols; D008752:Methylene Chloride; D012822:Silicon Dioxide; C031215:betadex; D000181:Acrylonitrile