You are here

Organocatalyzed synthesis of fluorinated poly(aryl thioethers).

Title: Organocatalyzed synthesis of fluorinated poly(aryl thioethers).
1 views
0 downloads
Name(s): Park, Nathaniel H, author
Gomes, Gabriel Dos Passos, author
Fevre, Mareva, author
Jones, Gavin O, author
Alabugin, Igor V, author
Hedrick, James L, author
Type of Resource: text
Genre: Journal Article
Text
Date Issued: 2017-08-01
Physical Form: computer
online resource
Extent: 1 online resource
Language(s): English
Abstract/Description: The preparation of high-performance fluorinated poly(aryl thioethers) has received little attention compared to the corresponding poly(aryl ethers), despite the excellent physical properties displayed by many polysulfides. Herein, we report a highly efficient route to fluorinated poly(aryl thioethers) via an organocatalyzed nucleophilic aromatic substitution of silyl-protected dithiols. This approach requires low catalyst loadings, proceeds rapidly at room temperature, and is effective for many different perfluorinated or highly activated aryl monomers. Computational investigations of the reaction mechanism reveal an unexpected, concerted SAr mechanism, with the organocatalyst playing a critical, dual-activation role in facilitating the process. Not only does this remarkable reactivity enable rapid access to fluorinated poly(aryl thioethers), but also opens new avenues for the processing, fabrication, and functionalization of fluorinated materials with easy removal of the volatile catalyst and TMSF byproducts.Fluorinated poly(aryl thioethers), unlike their poly(aryl ethers) counterparts, have received little attention despite excellent physical properties displayed by many polysulfides. Here the authors show a highly efficient route to fluorinated poly(aryl thioethers) via an organocatalyzed nucleophilic aromatic substitution of silyl-protected dithiols.
Identifier: FSU_pmch_28761127 (IID), 10.1038/s41467-017-00186-3 (DOI), PMC5537313 (PMCID), 28761127 (RID), 28761127 (EID), 10.1038/s41467-017-00186-3 (PII)
Publication Note: This NIH-funded author manuscript originally appeared in PubMed Central at https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5537313.
Persistent Link to This Record: http://purl.flvc.org/fsu/fd/FSU_pmch_28761127
Owner Institution: FSU
Is Part Of: Nature communications.
2041-1723
Issue: iss. 1, vol. 8

Choose the citation style.
Park, N. H., Gomes, G. D. P., Fevre, M., Jones, G. O., Alabugin, I. V., & Hedrick, J. L. (2017). Organocatalyzed synthesis of fluorinated poly(aryl thioethers). Nature Communications. Retrieved from http://purl.flvc.org/fsu/fd/FSU_pmch_28761127