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Self-Sorting Click Reactions That Generate Spatially Controlled Chemical Functionality on Surfaces

Author:
Arnold, Rachelle M., Locklin, Jason
Source:
Langmuir 2013 v.29 no.19 pp. 5920-5926
ISSN:
1520-5827
Subject:
alkynes, aminolysis, azides, biochemical compounds, chemical bonding, copper, dyes, equipment, fluorescence microscopy, polymerization, polymers, silicon, ultraviolet radiation
Abstract:
This Article describes the generation of a patterned surface that can be postpolymerization modified to incorporate fragile macromolecules or delicate biomolecules without the need for special equipment. Two monomers that undergo different click reactions, pentafluorophenyl acrylate (PFPA) and 4-(trimethylsilyl) ethynylstyrene (TMSES), were sequentially polymerized from a silicon surface in the presence of a shadowmask with UV light, generating 12.5 and 62 μm pitch patterns. Two different dyes, 1-aminomethylpyrene (AMP) and 5-azidofluorescein (AF), were covalently attached to the polymer brushes through aminolysis and dual desilylation/copper(I)-catalyzed alkyne/azide cycloaddition (CuAAC) in one pot. Unlike most CuAAC reactions, the terminal alkyne of TMSES was not deprotected prior to functionalization. Although a 2 nm thickness increase was observed for poly(PFPA) brushes after polymerization of TMSES, cross-contamination was not visible through fluorescence microscopy after functionalization.
Agid:
5767627