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New class of biodegradable polymers formed from reactions of an inorganic functional group
Journal article   Open access   Peer reviewed

New class of biodegradable polymers formed from reactions of an inorganic functional group

Jun Yoo, Denison J Kuruvilla, Sheetal R D'Mello, Aliasger K Salem and Ned B Bowden
Macromolecules, Vol.45(5), pp.2292-2300
2012
DOI: 10.1021/ma300190b
PMCID: PMC3311917
PMID: 22454554
url
https://www.ncbi.nlm.nih.gov/pmc/articles/3311917View
Open Access

Abstract

Although numerous small molecules have been synthesized with sulfenamide bonds (R(2)N-SR), this is the first report of the synthesis of polysulfenamides. These polymers are readily synthesized at room temperature using secondary diamines and dithiosuccinimides. The dithiosuccinimides were readily synthesized in one step by the reaction of dithiols such as HS(CH(2))(6)SH with N-chlorosuccinimide. The resulting dithiosuccinimides were either recrystallized or readily purified by chromatography on silica gel and required no special handling. The conversions of polymerization ranged from 95 to 98%, and the molecular weights of the polymer reached as high as 6,300 g mol(-1). The sulfenamide bond was very stable in organic solvents, and no degradation was observed under atmospheric conditions in C(6)D(6) for 30 days. In contrast, the sulfenamide bond readily decomposed in less than 12 h in D(2)O. Polysulfenamides were fabricated into micron-sized particles loaded with dye and endocytosed into JAWSII immature dendritic and HEK293 cells. Polysulfenamides represent a new class of polymers that are readily synthesized, stable in aprotic solvents, and readily degrade in water.

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