Synthesis and characterization of new thermally stable, antimicrobial and red-light-emitting poly(azomethine-ester)s
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Synthesis and characterization of new thermally stable, antimicrobial and red‑light‑emitting poly(azomethine‑ester)s Farah Qureshi1 · Muhammad Yar Khuhawar1 · Taj Muhammad Jahangir1 · Abdul Hamid Channar1 Received: 24 April 2020 / Revised: 24 August 2020 / Accepted: 27 August 2020 © Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Two new diphenol Schiff base monomers were prepared through condensation reaction between 4-hydroxybenzaldehyde and 4,4′-diaminodiphenyl sulfone (dapsone) or 1,2-cyclohexanediamine. The resulting Schiff bases were reacted with terephthaloyl dichloride through polycondensation and formed two novel poly(azomethine-ester) s. The molecular masses of diphenol Schiff bases were determined through E.I mass spectroscopy. The elemental composition of poly(azomethine-ester)s was evaluated through CHN analysis. The structures of diphenol Schiff bases and poly(azomethineester)s were confirmed though FT-IR, 1HNMR, UV–Vis spectroscopy, fluorescence, SEM and thermal analysis (TG/DTA). All the synthesized compounds were fluorescent and indicated 2–4 emission bands with maximum emission intensities within 342–682 nm at different excitation wavelengths. The diphenol Schiff bases showed violet-light emission, while their derived polyesters showed red-light emission. The poly(azomethine-ester)s indicated good thermal stability (347 °C and 561 °C) which was estimated through Tmax (temperature at which rate of weight loss is maximum) value obtained from DTG (derivative thermogravimetry) graph. The synthesized compounds were also tested for their antimicrobial activities against different species of bacteria and fungi. The Schiff base having dapsone moiety showed 55% inhibition, while its derived poly(azomethine-ester) showed 40% inhibition against bacterial species Shigella flexneri. Keywords Poly(azomethine-ester)s · Schiff bases · Thermal stability · Antimicrobial activities · Fluorescence emission Electronic supplementary material The online version of this article (https://doi.org/10.1007/s0028 9-020-03357-3) contains supplementary material, which is available to authorized users. * Farah Qureshi [email protected] 1
Institute of Advanced Research Studies in Chemical Sciences, University of Sindh, Jamshoro, Sindh, Pakistan
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Polymer Bulletin
Introduction Polyesters are renowned class of polymers due to their extensive range of applications which include coatings, fibers, films and packaging materials. These applications are based on the unique properties of polyesters which in turn depend on their structures; therefore, many researchers are attracted to study the effect of structural variation on the properties of polyesters [1]. The polymers containing azomethine (CH=N) units have many attracting properties such as thermal stability [2, 3], fluorescence [4–6], antimicrobial activities [7, 8] and their use as adsorbent for the removal of heavy metal ions from water systems [8, 9]. Therefore, a number of polyesters containing azomethine units al
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