Functionalization of polysulfones by using “Click” chemistry is described for the example of a small fluorescent analyte propargylpyrene. First, PSUs were converted to azido‐functionalized polymers by successive chloromethylation and azidation. Propargylpyrene was prepared independently as a fluorescent click component. Finally, the azido‐functionalized PSUs were coupled with propargylpyrene with high efficiency by copper‐catalyzed azide/alkyne click reactions. The final polymers and intermediates at various stages were characterized by 1H NMR, FT‐IR, GPC, UV‐Vis, and fluorescence spectroscopy techniques. magnified image
Preparation of new types of poly(amideimide)s with high thermal stability and improved solubility was investigated. Two new diimide-dicarboxylic acid containing pendent benzimidazole group, viz., 2-[3,5-bis(N-trimellitimidoyl)-phenyl] benzimidazole (DIDA-i) and 2-[3,5-bis(N-trimellitimidoyl)-phenyl] 5-methyl benzimidazole (DIDA-ii) from the condensation of 5-(2-benzimidazole)-1,3-phenylenediamine (DABI A ) and 5-(5-methyl-2-benzimidazole)-1,3-phenylenediamine (DABI B ) with trimellitic anhydride in glacial acetic acid were synthesized, respectively. 1,3-bis(N-trimellitimidoyl)benzene (DIDA-iii, as a reference) was also synthesized in a similar manner to study the properties of the its structure. Three series of aromatic poly(amide-imide)s were prepared by triphenyl phosphite-activated polycondensation from diimide-dicarboxylic acid DIDA-i, DIDA-ii, and the reference monomer DIDA-iii with various aromatic diamines. The polymers were obtained in quantitative yields with inherent viscosities between 0.46 and 0.81 dL g
À1. The effects of the benzimidazole pendent groups on the polymer properties, such as solubility and thermal stability were investigated by comparison of the polymers. The polymers bearing benzimidazole pendent groups exhibited thermal stability and good solubility in common polar solvents higher than the reference polymers.
Two new benzoxazole or benzothiazole-containing diimide-dicarboxylic acid monomers, such as 2-[3,5-bis(Ntrimellitimidoyl)phenyl]benzoxazole (2 o ) or 2-[3,5-bis(N-trimellitimidoyl)phenyl]benzothiazole (2 s ) were synthesized from the condensation reaction between 3,5-diaminobenzoic acid and 2-aminophenol or 2-aminothiophenol in polyphosphoric acid (PPA) with subsequent reaction of trimellitic anhydride in the presence of glacial acetic acid, respectively, and two new series of modified aromatic poly(amide-imide)s were prepared. This preparation was done with pendent benzoxazole or benzothiazole units from the newly synthesized diimide-dicarboxylic acid and various aromatic diamines by triphenyl phosphite-activated polycondensation. In addition, the corresponding unsubstituted poly(amide-imide)s were prepared under identical experimental conditions for comparative purposes. Characterization of polymers was accomplished by inherent viscosity measurements, FT-IR, UV-visible, 1 H-NMR spectroscopy and thermogravimetry. The polymers were obtained in quantitative yields with inherent viscosities between 0.39 and 0.81 dl g S1 . The solubilities of modified poly(amide-imide)s in common organic solvents as well as their thermal stability were enhanced compared to those of the corresponding unmodified poly(amide-imide)s. The glass transition temperature, 10% weight loss temperature, and char yields at 800-C were, respectively, 7-26-C, 17-46-C and 2-5% higher than those of the unmodified polymers.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.