Thiol–ene polymerization of oligospiroketal rods

Literature Information

Publication Date 2017-10-18
DOI 10.1039/C7PY01569K
Impact Factor 5.582
Authors

Pablo Wessig, Tanja Schulze, Alexandra Pfennig, Steffen M. Weidner, Sascha Prentzel, Helmut Schlaad


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Abstract

The nucleophilic thiol–ene (thia-Michael) reaction between molecular rods bearing terminal thiols and bis-maleimides was investigated. The molecular rods have oligospiroketal (OSK) and oligospirothioketal (OSTK) backbones. Contrary to the expectations, cyclic oligomers were always obtained instead of linear rigid-rod polymers. Replacing the OS(T)K rods with a flexible chain yielded polymeric products, suggesting that the OS(T)K structure is responsible for the formation of cyclic products. The reason for the preferred formation of cyclic products is due to the presence of folded conformations, which have already been described for articulated rods.

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