Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 5, Pages 1052-1059Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201603398
Keywords
click chemistry; gold nanoparticles; photochemistry; stained alkynes; surface modification
Categories
Funding
- Natural Sciences and Engineering Research Council (NSERC) of Canada Discovery Grants
- Ontario Graduate Scholarship
- Vanier Graduate Scholarship (P.G.) programs
- University of Western Ontario
- National Science Foundation (NSF) [CHE-1565646]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1565646] Funding Source: National Science Foundation
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In this study, we report the design, synthesis, and characterization of small 3 nm water soluble gold nanoparticles (AuNPs) that feature cyclopropenone-masked strained alkyne moieties capable of undergoing interfacial strain-promoted cycloaddition (i-SPAAC) with azides after exposure to UV-A light. A strained alkyne precursor was incorporated onto AuNPs by direct ligand exchange of a thiol-modified cyclopropenone-masked dibenzocyclooctyne (photoDIBO) ligand. These photoDIBO-AuNPs were characterized by H-1 NMR, IR, and UV/Vis spectroscopy, as well as transmission electron microscopy (TEM) and thermogravimetric analysis (TGA), and the extent of modification was quantified. Upon irradiation with UV-A light, photoDIBO-AuNPs underwent efficient and quantitative regeneration of the parent strained alkyne by photochemical decarbonylation to afford DIBO-derivatized AuNPs. DIBO-AuNPs were found to react cleanly and rapidly (k=5.3 x 10(-2)m(-1) s(-1)) by an interfacial strain-promoted alkyne-azide cycloadditon (i-SPAAC) with benzyl azide, which served as a simple model system. Furthermore, DIBO-AuNPs were reacted with various azides and a nitrone (interfacial strain-promoted alkyne-nitrone cycloaddition, iSPANC) to showcase the generality of this approach for the facile modification of AuNP surfaces and their properties. The cyclopropenone-based photo-triggered click chemistry at the interface of water-soluble AuNPs offers exciting opportunities for the atom-by-atom control and assembly of functional materials for applications in materials and biomaterials science as well as in chemical biology.
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