Versatility of Alkyne-Modified Poly(Glycidyl Methacrylate) Layers for Click Reactions

Journal Article · Sat Jan 01 04:00:00 EST 2011 · Langmuir

DOI:https://doi.org/10.1021/la2000798· OSTI ID:1014237

Soto-Cantu, Dr. Erick ^[1]; Lokitz, Bradley S ^[2]; Hinestrosa Salazar, Juan Pablo ^[3]; Deodhar, Chaitra ^[1]; Messman, Jamie M ^[2]; Ankner, John Francis ^[2]

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1. University of Tennessee, Knoxville (UTK)
2. ORNL
3. Clemson University

Functional soft interfaces are of interest for a variety of technologies. We describe three methods for preparing substrates with alkyne groups, which show versatility for 'click' chemistry reactions. Two of the methods have the same root: formation of thin, covalently attached, reactive interfacial layers of poly(glycidyl methacrylate) (PGMA) via spin coating onto silicon wafers followed by reactive modification with either propargylamine or 5-hexynoic acid. The amine or the carboxylic acid moieties react with the epoxy groups of PGMA, creating interfacial polymer layers decorated with alkyne groups. The third method consists of using copolymers comprising glycidyl methacrylate and propargyl methacrylate (pGP). The pGP copolymers are spin coated and covalently attached on silicon wafers. For each method, we investigate the factors that control film thickness and content of alkyne groups using ellipsometry, and study the nanophase structure of the films using neutron reflectometry. Azide-terminated polymers of methacrylic acid and 2-vinyl-4,4-dimethylazlactone synthesized via reversible addition-fragmentation chain transfer polymerization were attached to the alkyne-modified substrates using 'click' chemistry, and grafting densities in the range of 0.007-0.95 chains nm{sup -2} were attained. The maximum density of alkyne groups attained by functionalization of PGMA with propargylamine or 5-hexynoic acid was approximately 2 alkynes nm{sup -3}. The alkyne content obtained by the three decorating approaches was sufficiently high that it was not the limiting factor for the click reaction of azide-capped polymers.

• Research Organization: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS); Spallation Neutron Source
• Sponsoring Organization: USDOE Office of Science (SC)
• DOE Contract Number: AC05-00OR22725
• OSTI ID: 1014237
• Journal Information: Langmuir, Journal Name: Langmuir Journal Issue: 10 Vol. 27; ISSN 0743-7463
• Country of Publication: United States
• Language: English

Related Subjects

click chemistry
functional interfaces
neutron reflectometry