Polythioaminals from the Stabilization of Reactive Intermediates for Tailorable Surfaces
IBM Almaden Research Center
1,3,5-hexahydro-1,3,5-triazines (HTs) and their thermosetting polymer analogues, PHTs, have attracted recent attention in the materials space as they exhibit a number of attractive properties such as healability, facile preparation of anti-microbial surfaces, and even as detectors for heavy metals. HTs also demonstrate unique reactivity towards sulfur containing compounds. Hydrogen sulfide will, for instance, readily react with HTs at room temperature to form dithioazine, where the six-member HT ring undergoes replacement of two nitrogen atoms with sulfur. Organic thiols will also react with HTs to produce thioaminals, a transformation that was recently exploited to generate a new class of linear step-growth polymers, polythioaminals. The synthesis of polythioaminals are tolerant to a variety of substituents, functional groups, and monomers, and the subsequent polymers enable access to interesting post-polymerization chemistries such as the facile introduction of end-groups to produce functional oligomers. Subsequent studies of the formation of HTs have shown the use of electron withdrawing substituents on aromatic diamines extend the stability of reaction intermediates. In the presence of these intermediates dithiols could be readily reacted to form polythioaminals without the use HTs. The resulting reaction leads to linear polymers that possess monothioaminal linkages, moieties found to be latent crosslinks activated at higher temperatures and leading to the formation of chemically stable network polymers. This reactivity enabled access to a broader substrate diversity of polymers and polymer networks. Furthermore, using the chemically responsive behavior established in linear polythioaminals produced from HTs, end-group functionality could be introduced to these networks to produce tailorable surfaces and the introduction of desired functional groups. These networks possess an attractive characteristic of easy-to-process fluorinated polymers with applications that include hydrophobic coatings and adhesives and lithography.
Dr. Wojtecki graduated from Case Western Reserve University with a Ph.D. in Macromolecular Science & Engineering under the auspices of Stuart J. Rowan, now at the Univ. of Chicago. His research focused on the synthesis of mechanically interlocked polymers composed of catenanes, chemical units that were the subject of the 2016 Nobel prize in chemistry on molecular machines (catenanes & rotaxanes). This work was recently accepted into the journal Science in a report titled “Poly[n]catenanes: The Synthesis of Molecular Chains.” Rudy joined IBM Almaden Research Center after completion of his graduate work. He is an author/co-author of 19 peer reviewed scientific publications including a Nature Materials Review article. In 2017 he was recognized as an IBM Master Inventor for work highlighted in 35 issued patents. Rudy’s current research efforts are geared to address ongoing challenges for lithography and patterning materials used in the manufacturing of semiconductors that include selective deposition schemes using atomic layer deposition and extreme ultraviolet lithography.
Wednesday, December 20, 2017
Michael’s at Shoreline
2960 N Shoreline Blvd
Mountain View, CA
6 PM social hour
7 PM dinner
8 PM lecture
|Walk-in (not guaranteed)
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