A Multisegmented Polystyrene with pH-Cleavable Linkages 


Vol. 35,  No. 9, pp. 2694-2698, Sep.  2014
10.5012/bkcs.2014.35.9.2694


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  Abstract

A multisegmented polystyrene (PS) with pH-cleavable ester and carbamate linkages was successfully synthesized by a combination of atom transfer radical polymerization (ATRP) and Cu(I)-catalyzed 1,3-dipolar cycloaddition of azide and alkynes (click chemistry). ATRP was employed to synthesize polystyrene from hydroxyl-terminated initiator using CuBr/N,N,N',N'',N''-pentamethyldiethylenetriamine (PMDETA) as the catalyst. The reaction of the resulting PS with sodium azide yielded the azido-terminated polymer. The hydroxyl group in the other end of the polymer was reacted with 4-nitrophenyl chloroformate (NPC), followed by reaction with propargylamine to produce an alkyne end group with a carbamate linkage. The PS with an alkyne group in one end and an azide group in the other end was then self-coupled in the presence of CuBr/2,2'- bipyridyl (bpy) in DMF to yield a desired multisegmented PS. Molecular weight and molecular weight distribution of the self-coupled polymer increased with time, as in the typical step-growth-type polymerization processes. Finally, we demonstrated that the ester and carbamate linkages of the multisegmented PS were hydrolyzed in the presence of HCl to yield individual PS chains.

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  Cite this article

[IEEE Style]

T. Kang and H. Lee, "A Multisegmented Polystyrene with pH-Cleavable Linkages," Bulletin of the Korean Chemical Society, vol. 35, no. 9, pp. 2694-2698, 2014. DOI: 10.5012/bkcs.2014.35.9.2694.

[ACM Style]

Tae-Hyeon Kang and Hyung-il Lee. 2014. A Multisegmented Polystyrene with pH-Cleavable Linkages. Bulletin of the Korean Chemical Society, 35, 9, (2014), 2694-2698. DOI: 10.5012/bkcs.2014.35.9.2694.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949