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- Title
Synthesis of small water-soluble diazirine-functionalized gold nanoparticles and their photochemical modification.
- Authors
Ghiassian, Sara; Biesinger, Mark C.; Workentin, Mark S.
- Abstract
Dual water and organic solvent soluble 3-aryl-3-(trifluormethyl) diazirine-functionalized gold nanoparticles (AuNPs) were prepared through a place exchange reaction from triethylene glycol monomethyl ether (EG3-Me) capped AuNPs. These nanoparticles were fully characterized using 1H and 19F nuclear magnetic resonance (NMR) spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), and X-ray photoelectron spectroscopy (XPS). TGA along with 1H NMR data allowed the determination of 15% incorporation of diazirine (Diaz) ligands onto mixed monolayer AuNPs, while TEM images showed an average diameter of 2.3 ± 0.5 nm. This information led to the estimated molecular formula of Au400 (S-EG4-Diaz)40 (S-EG3-Me)230 for these AuNPs. It is noteworthy that high-resolution XPS was a powerful tool for quantitative analysis. Irradiation of the diazirine capped AuNPs resulted in nitrogen extrusion and the formation of a highly reactive carbene with evidence of a portion of the reaction proceeding via the diazo intermediate and thus requiring a second photon for activation. The carbene species generated was utilized to tether the attached AuNPs via insertion into C=C or O-H functionality inherent on various substrates. Here, we demonstrated that photolysis of the diazirine modified AuNPs in the presence of a variety of model carbene scavengers led to clean and efficient insertion products while maintaining their solubility in polar solvents.
- Subjects
DIAZIRINES; GOLD nanoparticle synthesis; HYDROPHILIC compounds; PHOTOCHEMISTRY; ORGANIC solvents; ETHYLENE glycol; NUCLEAR magnetic resonance
- Publication
Canadian Journal of Chemistry, 2015, Vol 93, Issue 1, p98
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/cjc-2014-0287