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Paper Information

Journal:   JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS)   FEBRUARY 2014 , Volume 11 , Number 1; Page(s) 75 To 83.
 
Paper: 

SYNTHESIS OF NEW NANOCOPOLYMER CONTAINING β-LACTAMS

 
 
Author(s):  JARRAHPOUR ALIASGHAR*, HEIRAN ROGHAYEH
 
* DEPARTMENT OF CHEMISTRY, COLLEGE OF SCIENCES, SHIRAZ UNIVERSITY, 71454, SHIRAZ, IRAN
 
Abstract: 

Several new monocyclic b-lactam monomers bearing the NO2 group 2a-g were synthesized via a [2+2] ketene-imine cycloaddition reaction (Staudinger reaction). Calculation of coupling constant of H-3 and H-4, and the X-ray crystallography of b-lactam 2e confirmed the cis stereochemistry of these b-lactams. Then aminophenyl b-lactams were synthesized by the reduction of NO2 to NH2 group in the presence of Raney Ni and hydrazines hydrate. Treatment of these aminophenyl b-lactams with acryloyl chloride and sodium bicarbonate (NaHCO3), afforded the monomers bearing the NHCOCH=CH2 group. These acrylated b-lactam monomers were dissolved in a warm mixture of butyl acrylate and styrene and then were converted to the corresponding polyacrylate nano b-lactams by emulsion polymerization in water. A unique feature of this methodology is the ability to incorporate water-insoluble compounds directly into the nanoparticle framework. Structures of the synthesized compounds were confirmed by physical and spectral analyses. Dynamic light scattering analysis and transmission electron microscopy of the final emulsions show that the nanoparticles were about 50–70 nm in diameter.

 
Keyword(s): 2-AZETIDINONE, [2+2] CYCLOADDITION, STAUDINGER REACTION, POLYACRYLATE NANOPARTICLES
 
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