Silylated oligomeric poly(ether-azomethine)s from monomers containing biphenyl moieties: synthesis and characterization

Abstract

In this study, four new silicon-containing poly(ether-azomethine)s with linear structures were prepared using original silicon and biphenyl moiety-containing monomers: two diamines and two dialdehydes.

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

“…These results indicate that no significant impact on the polymer solubility was observed when changing the R group bonded to the silicon atom (methyl or phenyl). These results are contradictory to those previously obtained by our research group, where the difference in volume between both groups markedly modified the solubility of silylated materials . Probably, the structural rigidity of the PAzMC chains is a factor that strongly conditions their solubility behavior.…”

“…However, in both cases, a complete assignment of the signals was developed. Likewise, both H NMR spectra evidenced a signal at ca 10 ppm, attributable to carbonyl end‐group characteristic of oligomeric PAzMs . A singlet at −2.37 ppm in the C NMR spectrum of PAzMC1 (Fig.…”

“…4,4′‐(9‐Fluorenylidene)dianiline ( 1 ), p ‐toluenesulfonic acid ( p ‐TsOH), anhydrous DMAc and anhydrous calcium sulfate were purchased from Aldrich Chemical (Milwaukee, WI, USA). Bis(4‐formylbiphenyl‐4‐yl)dimethylsilane ( 2 ) and bis(4‐formylbiphenyl‐4‐yl)diphenylsilane ( 3 ) were synthesized according to previously described procedures …”

“…In this sense, some strategies for improving the in‐solution processabilities of PAzMs have been addressed by several authors, such as incorporating bulky substituents or halogen atoms on the aromatic rings, using aliphatic/aromatic side‐chains or ether linkages as solubilizing groups . The introduction of di‐R‐diphenylsilane units (PhSiR 2 Ph, where R = methyl or phenyl) has recently been successfully used to improve the solution processability of PAzMs . These units give flexibility to their aromatic backbone by introducing polar SiC bonds, which allow greater freedom of rotation of the main chain, compared to CC bonds.…”

Synthetic Methodologies for Chelating Polymer Ligands: Recent Advances and Future Development

“…Four silicon‐containing poly(ether‐azomethine)s with linear structures were obtained using initial monomers containing silicon and biphenyl silicon and biphenyl moiety: two diamines and two dialdehydes. The oligomeric natures of the samples were established, in which chains containing 3 to 5 repetitive units are shown . Poly (azomethine ether)s were also synthesized by elimination reactions of aromatic dihydroxy compounds containing imines that bind to terephthaloyl chloride (Scheme ) …”