Synthesis of secondary arylamine copolymers with Iron(II) clathrochelate units and their functionalization into tertiary Polyarylamines via Buchwald-Hartwig cross-coupling reaction. (12th September 2019)

• Record Type: Journal Article
• Authors: Shetty, Suchetha; Baig, Noorullah; Al-Mousawi, Saleh; Al-Sagheer, Fakhreia; Alameddine, Bassam
• Is Part Of: Polymer. Volume 178(2019)
• Publication Date: 2019-09-12
• Subjects: Inorganic polymers -- Functionalization of polymers -- Polyaniline -- C-N cross-coupling -- ESCA/XPS; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.polymer.2019.121606
• Languages: English
• ISSNs: 0032-3861

Abstract

Abstract: We report the synthesis of three secondary arylamine copolymers bearing iron(II) clathrochelate units (CLP1-3 ). Three of the latter copolymers were post-modified into their tertiary arylamine moieties (PCLP1-3 ) using a mild palladium-catalyzed Buchwald-Hartwig cross-coupling reaction. Interestingly, the functionalization of the secondary arylamine groups has resulted in the formation of highly soluble target compoundsPCLP1-3, which allowed for their simple isolation and full analysis via various techniques. It is noteworthy that a prototypical secondary arylamine iron(II) clathrochelate monomerCLM1 was synthesized and post-modified into its tertiary arylamine target compoundCLM2 . The current study discloses the first examples on making secondary arylamine copolymers with clathrochelate constituents, and proves the possible post-modification of the latter compounds into tertiary arylamine, which proves the modularity of iron(II) clathrochelate unit to make functional polymers. Formation of the monomers and copolymers was confirmed by 1 H- and 13 C- nuclear magnetic resonance (NMR), gel permeation chromatography (GPC), X-ray photoelectron spectroscopy (XPS), Thermogravimetric Analysis (TGA), scanning electron microscopy (SEM), and UV–Vis absorption spectroscopy. Graphical abstract: Image 1 Highlights: Synthesis of secondary arylamine copolymers with iron(II) clathrochelates units is reported. The resulting copolymers were functionalized to their corresponding tertiary arylamines. The highly soluble target copolymers were isolated in high yields. First report on making secondary and tertiary arylamine copolymers bearing clathrochelate units. Clathrochelate complexes prove they can withstand Buchald-Hartwig reaction conditions.