Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 19, Pages 5777-5783Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201500485
Keywords
modular ligation; nitrogen heterocycles; polymerization; stable nitrile oxides; surface analysis
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Funding
- Karlsruhe Institute of Technology (KIT)
- Alexander von Humboldt Foundation
- Grant Agency of the Czech Republic (GACR) [P20512G118]
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The efficient trapping of photogenerated thioaldehydes with functional shelf-stable nitrile oxides in a 1,3-dipolar cycloaddition is a novel and versatile photochemical strategy for polymer end-group functionalization and surface modification under mild and equimolar conditions. The modular ligation in solution was followed in detail by electrospray ionization mass spectrometry (ESI-MS). X-ray photoelectron spectroscopy (XPS) was employed to analyze the functionalized surfaces, whereas time-of-flight secondary-ion mass spectrometry (ToF-SIMS) confirmed the spatial control of the surface functionalization using a micropatterned shadow mask. Polymer brushes were grown from the surface in a spatially confined regime by surface-initiated atom transfer radical polymerization (SI-ATRP) as confirmed by TOFSIMS, XPS as well as ellipsometry.
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