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. 2014 Sep 1;53(36):9466-9470.
doi: 10.1002/anie.201403758. Epub 2014 Aug 5.

SuFEx-based synthesis of polysulfates

Jiajia Dong #  1 , K Barry Sharpless  1 , Luke Kwisnek #  2 , James S Oakdale #  2 , Valery V Fokin  2
Affiliations

SuFEx-based synthesis of polysulfates

Jiajia Dong et al. Angew Chem Int Ed Engl. .

Abstract

High-molecular-weight polysulfates are readily formed from aromatic bis(silyl ethers) and bis(fluorosulfates) in the presence of a base catalyst. The reaction is fast and proceeds well under neat conditions or in solvents, such as dimethyl formamide or N-methylpyrrolidone, to provide the desired polymers in nearly quantitative yield. These polymers are more resistant to chemical degradation than their polycarbonate analogues and exhibit excellent mechanical, optical, and oxygen-barrier properties.

Keywords: SuFEx reaction; click chemistry; polymerization.

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Figures

Figure 1
Figure 1
GPC (UV detector) traces to accompany Table 1.
Figure 2
Figure 2
Hydrolytic stability of polysulfate comparing to polycarbonate (as judged by GPC analysis).
Figure 3
Figure 3
Relationship between Tg and Mn for representative BPA polysulfates. Inset provides DSC second heating thermograms. Line provided to guide the eye.
Figure 4
Figure 4
Precipitated, unprocessed BPA polysulfate on the left. Compression molded BPA polysulfate film on the right.
Scheme 1
Scheme 1
(a) Preparation of fluorosulfate and silyl ether monomers from Bisphenol-A; (b) Synthesis of polysulfates. Mn is in reference to polystyrene standards (GPC). TMS, trimethylsilyl; TBS, tert-butyl-dimethylsilyl; TBDPS, tert-butyldiphenylsilyl; TIPS, triisopropylsilyl.
See this image and copyright information in PMC

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