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Synthesis, Characterization and Reactivity of Iodosylbenzene Nanoparticles as a New Nano–reagent
Author(s) -
Zakavi Saeed,
motlagh Reza Jafari
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601246
Subject(s) - reactivity (psychology) , dynamic light scattering , nanoparticle , oxidizing agent , reagent , chemistry , solubility , scanning electron microscope , catalysis , reducing agent , nuclear chemistry , materials science , organic chemistry , nanotechnology , medicine , alternative medicine , composite material , pathology
Iodosylbenzene (PhIO) and its derivatives are efficient terminal oxidants that have gained considerable attention. However, it suffers from limited solubility in most organic solvents and water. In the present study, the nanoparticles of iodosylbenzene has been synthesized with the aim of enhancing solubility in different solvents and its reactivity in oxidation reactions without any change in its chemical composition. Controlled alkaline hydrolysis of iodobenzene diacetate in the presence of (triethyleneglycol)monomethyl ether as stabilizer produced the nanoparticles. The average radius of the nanostructures determined by dynamic light scattering (DLS) and atomic force microscopy (AFM), was 149 and 71 nm, respectively. Also, the maximum height of nanoparticles measured from AFM images was 16 nm. Furthermore, scanning electron microscopy‐energy dispersive X‐ray analysis (SEM‐EDX) confirmed the formation of non‐spherical iodosylbenzene nanoparticles. The results of 1 H and 13 C NMR studies in DMSO‐d 6 are in accord with the existence of different oligomeric iodosylbenzene particles in solution. This observation was also confirmed by the superimposed FT‐IR spectra of the bulk and nano‐sized products. Non‐catalytic oxidation of 1,5‐naphthalenediol to juglone with the bulk and nano‐sized oxidants, also the oxidation of styrene in the absence and presence of meso ‐tetraphenylporphyrinatomanganese(III) acetate, confirmed the increased oxidizing ability of the nano‐sized oxidant.