Benzoxazine monomers containing triphenylimidazole: Polymerization of monomers and properties of polybenzoxazines. (December 2019)

• Record Type: Journal Article
• Authors: Li, Xufeng; Liu, Yijiang; Chen, Hongbiao; Li, Huaming
• Is Part Of: European polymer journal. Volume 121(2019)
• Publication Date: 2019-12
• Subjects: Triphenylimidazole -- Thermal polymerization -- Polybenzoxazine -- Spectral property; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; Polymerization; Polymers; Periodicals; Electronic journals; 547.705
• DOI: 10.1016/j.eurpolymj.2019.109347
• Languages: English
• ISSNs: 0014-3057

Abstract

Graphical abstract: Highlights: Novel benzoxazine monomers containing triphenylimidazole moieties are synthesized. A structural rearrangement is observed during the thermal ring-opening polymerization. Poly-TBZ and poly-MTBZ are soluble in common organic solvents. The poly-TBZ shows the acid-dependent spectral properties. The poly-MTBZ can be used as a selective chemodosimeter for the detection of Ag + . Abstract: In this study, two novel benzoxazine monomers containing triphenylimidazole (TBZ) and triphenylimidazolium (MTBZ) moieties are synthesized and fully characterized. The thermal ring-opening polymerization process of the two monomers is monitored by the 1 H NMR and GPC analyses, which demonstrates that such a polymerization proceeds through a rearrangement of ketal-type linkage in the main chain into Mannich-type polymer along with the fast increasing in molecular weight. The structures of the triphenylimidazole-containing polybenzoxazines, poly-TBZ and poly-MTBZ, are verified by 1 H NMR and FT-IR spectroscopies, and the thermal and mechanical properties of such polybenzoxazines are investigated by TGA and DMA analyses. Owing to the good solubility of poly-TBZ and poly-MTBZ in common organic solvents, poly-TBZ can be easily converted into poly-MTBZ through a facile post-modification approach. More importantly, the poly-TBZ shows the acid-dependent spectral properties due to formation of amine salts, whereas poly-MTBZ can be used as a chemodosimeter for the detection of Ag +, which exhibits high selectivity, good linearity and naked-eye distinguishable color change. This strategy can be utilized to prepare triphenylimidazole-containing polybenzoxazines with good solubility and tunable spectral properties, thereby extending their functionalities and applications.