Synthesis of oligo‐ortho‐azomethinephenol and its oligomer–metal complexes: Characterization and application as anti‐microbial agents

Abstract

ABSTRACT:The oxidative polycondensation reaction conditions and optimum parameters of o-phenylazomethinephenol (PAP) with oxygen (air) and NaOCl were determined in an aqueous alkaline solution at 60 -98°C. The properties of oligo-o-phenylazomethinephenol (OPAP) were studied by chemical and spectra analyses. PAP was converted to dimers and trimers (25-60%) by oxidation in an aqueous alkaline medium. The number average molecular weight (M n ), mass average molecular weight (M w ), and polydispersity index (PDI) values were 1180 g mol Ϫ1 , 1930 g mol Ϫ1 , and 1.64, respectively. According to these values, 20 -33% of PAP turned into OPAP. During the polycondensation reaction, a part of the azomethine (OCHANO) groups oxidized to carboxylic (OCOOH) group. Thus, a water-soluble fraction of OPAP was incorporated in the carboxylic (OCOOH); (2-20%) group. Also, the structure and properties of oligomermetal complexes of OPAP with Cu(II), Ni(II), Zn(II), and Co(II) were studied. Antimicrobial activites of the oligomer and its oligomer-metal complexes were tested against B. cereus, L. monocytogenes, B. megaterium, B. subtilis, E. coli, Str. thermophilus, M. smegmatis, B. brevis, E. aeroginesa, P. vulgaris, M. luteus, S. aureus, and B. jeoreseens. Also, according to differential thermal analysis and thermogravimetric analysis, OPAP and its oligomer-metal complexes were stable throughout to temperature and thermooxidative decomposition.

A novel polyphenol: synthesis, characterization and investigation of its thermal and electrochemical properties

“…The small peak at 1677 cm À1 was attributed to the carbonyl (C ¼ O) stretching vibration, which may be formed by oxidation of the imine groups within the polymer pendent groups. 8,11 These data showed that the polymer obtained from 4-PHMP was also composed of a mixture of phenylene and oxyphenylene units.…”

“…Thus far, the detailed polymerization behaviors of the oxidative polycondensation of NO-type phenoxy imines have been widely investigated by Kaya et al and others. [9][10][11] However, the polymerization of NNO-type phenoxy-ketimine or phenoxy-imine monomers has not yet been studied. Previously, we focused on the formation of NNO-type poly(phenoxy-ketimine).…”

Poly(phenoxy-imine)s and Poly(phenoxy-ketimine)s: Toward New Semiconductive Polymeric Materials

“…They are promising candidates for a wide variety of applications such as optoelectronics [1,2], semiconductor [3], electrochromic [4], antistatic [5] and antimicrobial [6] materials by adding other functional groups. Efforts were focused to improve the electrooptical properties of polyphenols with longer conjugated segments.…”

Synthesis, Characterization and Biological Studies of New Linear Thermally Stable Schiff Base Polymers with Flexible Spacers

“…[14][15][16] The Schiff base polymers demonstrate antimicrobial activity against bacteria, yeast and fungi. 17,18 Thus these can be used for the purification of industrial contaminants from heavy metals and microbiological organisms and are significant for environmental applications. These polymers are also being studied for the applications of optoelectronics.…”