AVS 47th International Symposium
    Biomaterial Interfaces Wednesday Sessions
       Session BI-WeA

Paper BI-WeA5
Synthesis and Characterization of Functionalized Polymerizable Diacetylene Containing Thiol Monolayers

Wednesday, October 4, 2000, 3:20 pm, Room 202

Session: Non-fouling Surfaces
Presenter: N.R. Holcomb, Agilent Technologies
Authors: N.R. Holcomb, Agilent Technologies
D.G. Castner, University of Washington
D.W. Grainger, Colorado State University
Correspondent: Click to Email
Self-assembled structures have been used to tailor the surface character of materials: enhance adhesion, lubrication, catalysis, and molecular/cell immobilization and recognition in biotechnology.@footnote 1,2@ Utilization of polymeric materials in the self-assembling monolayer can increase the thermal and mechanical strength of the films formed from monomeric materials.@footnote 3@ The use of polymeric blocks within self-assembled films has shown that there is added stability toward solvent attack.@footnote 4,5@ We report the synthesis and characterization of new surface functional diacetylene thiols of the formula: R-(CH2)n-C?C-C?C-(CH2)m-SH where n=m=9, and R=fluoro alkyl, or oligoethylene glycol. These materials were synthesized via multistep schemes featuring an asymmetric Cadiot-Chodkiewicz coupling to create the functional diacetylenes from pairs of alkynes. Self-assembled monolayers of these organic molecules are characterized with polarized FTIR, ellipsometry, contact angle, XPS and TOF-SIMS. Films were formed from diacetylene thiols containing contrasting surface functional groups to provide a triethylene glycol non-biofouling surface@footnote 6@ and a low surface energy fluorinated surface.@footnote 3@ @FootnoteText@ @footnote 1@ K. M. McClary, D. W. Grainger, Biomaterials, 20, 1999, 2435-2446 @footnote 2@ K. M. McClary, D. W. Grainger J. Biomed. Mater. Res., in press (2000). @footnote 3@ Ebert, R.; Laschewsky, A.; Ringsdorf, H.; J. Am. Chem. Soc. 1985, 107, 4134 @footnote 4@ Sun, F.; Grainger, D.W.; J. Polym Sci. Polym. Chem. Ed. 1993, 31, 172 @footnote 5@ Sun, F.; Castner, D.G.;Grainger, D.W.; Langmuir. 1993, 9, 3200 @footnote 6@ Pertsin, A. J.; Grunze, M.; Garbuzova, I. A. J. Phys. Chem. B 1998, 102, 4918-4926.