Hydroaminoalkylation for Amine Functionalization of Vinyl-Terminated Polyethylene Enables Direct Access to Responsive Functional Materials.

Autor: Ataie S; Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, V6T 1Z1, Canada., Malmir A; Department of Chemical and Biological Engineering, University of British Columbia, Vancouver, British Columbia, V6T 1Z3, Canada., Scott SS; Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, V6T 1Z1, Canada., Goettel JT; Centre for Applied Research, NOVA Chemicals, Calgary, Alberta, T2E 7K7, Canada., Clemens SN; Centre for Applied Research, NOVA Chemicals, Calgary, Alberta, T2E 7K7, Canada., Morrison DJ; Centre for Applied Research, NOVA Chemicals, Calgary, Alberta, T2E 7K7, Canada., Mackie C; Department of Chemistry, University of Calgary, Calgary, Alberta, T2N 1N4, Canada., Heyne B; Department of Chemistry, University of Calgary, Calgary, Alberta, T2N 1N4, Canada., Hatzikiriakos SG; Department of Chemical and Biological Engineering, University of British Columbia, Vancouver, British Columbia, V6T 1Z3, Canada., Schafer LL; Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, V6T 1Z1, Canada.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Dec 02; Vol. 63 (49), pp. e202410154. Date of Electronic Publication: 2024 Oct 30.
DOI: 10.1002/anie.202410154
Abstrakt: While functionalized polyethylenes (PEs) exhibit valuable characteristics, the constraints of existing synthetic approaches limit the variety of readily incorporated functionality. New methods to generate functionalized PEs are required to afford new applications of this common material. We report 100 % atom economic tantalum-catalyzed hydroaminoalkylation of vinyl-terminated polyethylene (VTPE) as a method to produce amine-terminated PE. VTPEs with molecular weights between 2200-16800 g/mol are successfully aminated using solvent-free conditions. Our catalytic system is efficient for the installation of both aromatic and aliphatic amines, and can be carried out on multigram scale. The associating amine functional groups afford modified material properties, as measured by water contact angle, differential scanning calorimetry (DSC) and polymer rheology. The basic amine functionality offers the opportunity to convert inert PE into stimuli-responsive materials, such that the protonation of aminated PE affords the generation of functional antibacterial PE films.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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