Diazonium salt-mediated synthesis of new amino, hydroxy, propargyl, and maleinimido-containing superparamagnetic Fe@C nanoparticles as platforms for linking bio-entities or organocatalytic moieties
- 266 Downloads
New magnetic Fe@C nanoparticles in the size range of about 20–50 nm functionalized with amino, hydroxy, propargyl, or maleinimido groups were synthesized by reaction with aryl diazonium salts. Aryl diazonium salts wherein the functional groups are linked via a sulfonamide moiety turned out to be advantageous over those with direct linkage. The obtained Fe@C nanoparticles represent magnetic nanoplatforms for linking bio-entities and organocatalysts using amide formation, CuAAC, or thiol-ene click chemistry as exemplified by selected examples. The Fe@C nanoparticles obtained exhibit supramolecular behavior with high value of saturation magnetization rendering them attractive for practical applications in biomedicine and organocatalysis.
KeywordsMagnetic nanoparticles Click chemistry Diazonium salts Biotin Sulfonamides Carbon shell
The authors wish to acknowledge Dr. Ioan Bratu for FTIR measurements, Dr. Cristian Leostean for conducting XPS and magnetic measurements, Dr. Lucian Barbu for TEM investigations.
- Accelrys Software Inc. (2010) Materials Studio, Release 5.5Google Scholar
- Belmont J, Amici R, Galloway C (1995) Carbon black reacted with diazonium salts and products. W. I. P. Organization WorldGoogle Scholar
- Cheong S, Ferguson P, Feindel KW, Hermans IF, Callaghan PT, Meyer C, Slocombe A, Su CH, Cheng FY, Yeh CS, Ingham B, Toney MF, Tilley RD (2011) Simple synthesis and functionalization of iron nanoparticles for magnetic resonance imaging. Angew Chem Int Ed 50(18):4206–4209. doi: 10.1002/anie.201100562 CrossRefGoogle Scholar
- Dumitrache F, Morjan I, Alexandrescu R, Morjan RE, Voicu I, Sandu I, Soare I, Ploscaru M, Fleaca C, Ciupina V, Prodan G, Rand B, Brydson R, Woodword A (2004) Nearly monodispersed carbon coated iron nanoparticles for the catalytic growth of nanotubes/nanofibres. Diam Relat Mater 13(2):362–370. doi: 10.1016/j.diamond.2003.10.022 CrossRefGoogle Scholar
- Dumitrache F, Morjan I, Fleaca C, Birjega R, Vasile E, Kuncser V, Alexandrescu R (2011) Parametric studies on iron-carbon composite nanoparticles synthesized by laser pyrolysis for increased passivation and high iron content. Appl Surf Sci 257(12):5265–5269. doi: 10.1016/j.apsusc.2010.11.069 CrossRefGoogle Scholar
- Klug HP, Alexander LE (1974) X-Ray diffraction procedures. Wiley, New York, pp 687–703Google Scholar
- Lindberg BJ, Hedman J (1975) Molecular spectroscopy by means of Esca.6. Group shifts for N, P and as compounds. Chem Scr 7(4):155–166Google Scholar
- Morjan I, Alexandrescu R (2014) New advances in the production of iron-based nanostructures manufactures by laser pyrolysis. In: Nirschl H, Keller K (eds) Upscaling of bio-nano-processes. Springer, Heidelberg, pp 15–37Google Scholar
- Zeltner M, Grass RN, Schaetz A, Bubenhofer SB, Luechinger NA, Stark WJ (2012) Stable dispersions of ferromagnetic carbon-coated metal nanoparticles: preparation via surface initiated atom transfer radical polymerization. J Mater Chem 22(24):12064–12071. doi: 10.1039/C2jm31085f CrossRefGoogle Scholar