Triptycene-containing Poly(vinylene sulfone) derivatives from a metal-free thiol-yne click polymerization followed by a mild oxidation reaction. (10th October 2018)

• Record Type: Journal Article
• Authors: Alameddine, Bassam; Baig, Noorullah; Shetty, Suchetha; Al-Mousawi, Saleh; Al-Sagheer, Fakhreia
• Is Part Of: Polymer. Volume 154(2018)
• Page Start: 233
• Page End: 240
• Publication Date: 2018-10-10
• Subjects: Click-chemistry -- Catalyst-free polymerization -- CS bond formation -- Poly(thioethers) -- Polysulfones; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.polymer.2018.09.020
• Languages: English
• ISSNs: 0032-3861

Abstract

Abstract: Triptycene-derived vinyl sulfide polymers4a-d were synthesized from a versatile catalyst-free thiol-yne click reaction using 1, 4-diethynyl triptycene1 with various aryl dithiol building blocks3a-d . The resulting triptycene-bearing poly(vinylene sulfide)s4a-d display excellent solubility and chemical stability allowing for their structural, thermal, and photophysical characterization by various instrumental analysis techniques. The thioether groups in polymers4a-d were selectively oxidized into their respective sulfone derivatives via mild reaction conditions affording the corresponding triptycene-based poly(vinylene sulfone)s5a-d in quantitative yield. Graphical abstract: Highlights: New triptycene-based poly(vinyl sulfide)s from metal free thiol-yne click chemistry. Polymers were oxidized into their sulfone homologues via mild reaction conditions. Selective oxidation of the thioether where vinyl groups weren't affected. Only triptycene-based poly(vinyl sulfone)s formed with no presence of sulfoxides. Prototypical monomers found to have an E, E configuration of their vinyl groups.