Synthesis and physicochemical studies of ferrocene-containing materials (original) (raw)
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Some New Organometallic Polyamides based on Ferrocene
Journal of Inorganic and Organometallic Polymers and Materials, 2007
Ferrocenedicarbonyl chloride was reacted with three different types of aromatic diamines via solution polycondensation to get three new polyamides. Two of which were soluble in some organic solvents. The resulting polymers were characterized by their solubilities, viscosity measurements, elemental analysis, FTIR spectroscopy, differential scanning calorimetric and thermogravimetric studies. Fe C O C O NH NH Ar n
Research Square (Research Square), 2022
Efforts have been devoted to synthesize and characterize processable polymers with desired properties. Herein, four different series of aromatic and aliphatic terpolyamides were prepared via solution phase polycondensation of 4,4'-oxydianiline and hexamethylenediamine (HMDA) with various diacids chlorides (isophthalyol dichloride, terepthalyol dichloride, 1, 1'-ferrocene dicarboxylic acid chloride and transazobenzene-4, 4'-dicarbonyl chloride). The structural, morphological and physico-chemical nature of as prepared polymers was explored by Fourier-transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), thermal analysis (TGA and DSC), and wide-angle x-ray diffraction (WAXRD). Moreover, an aliphatic diamine was incorporated in varying concentration as a exible methylene spacer and the effect of its concentration on the properties of polyamides was also studied. Changes in various physicochemical properties such as solubility, inherent viscosity, surface morphology and ame retarding behaviour were investigated. Marked difference in morphology and solubility was observed with the change in the ratio of segments in the chain. Inherent viscosities of polymers ranged from 1.8052-1.6274 dl/g indicating reasonably moderate molecular weights. Interestingly, ferrocene based aromatic polymers were more thermally stable (T g 260 o C, T i 310 o C, T h 525 o C, T f 720 o C, for PF 0), and also found to exhibit best ame retarding behavior (limiting oxygen index (LOI) value for PF 0 is LOI 33.15 %).
Synthesis and characterization of some novel organometallic aromatic polyamides
Applied Organometallic Chemistry, 2006
Some novel ferrocene containing aromatic polyamides were prepared by low-temperature solution phase polycondensation of 1,1 -ferrocenedicarboxylic acid chloride with some newly synthesized aromatic diamines in tetrahydrofuran, in the presence of triethylamine. The amorphous polymers were derived in good yields, and did not melt at >350 • C. The monomers and the resulting polymers were characterized by their physical properties, elemental analysis, 1 H-NMR, FTIR spectroscopy, differential scanning calorimetry and thermogravimetric analyses. The polymeric products were insoluble in common solvents tested. However, all were miscible in concentrated H 2 SO 4 , forming reddish brown solutions at ambient conditions. The glass transition temperatures (T g ) of these polymers were quite high, which is characteristic of aramids. They are stable up to 500 • C, with 10% mass loss observed in the range 400-650 • C. The activation energies of pyrolysis for each of the products were calculated by Horowitz and Metzger's method. Solution viscosities of the polymers were reduced in concentrated sulfuric acid, which is due to their non-Newtonian behavior.
Journal of Inorganic and Organometallic Polymers and Materials, 2013
Three kinds of polyfunctional polyols with hydroxyl values of 180-320 mg/g were prepared by the reaction of hydrogenated terpinene-maleic ester type epoxy resin with secondary amines (diethylamine, N-methylethanolamine, and diethanolamine), and the chemical structures were characterized by Fourier transform infrared spectroscopy and NMR spectroscopy. These polyols were used in place of commonly used polyols to prepare twocomponent polyurethanes when reacted with polyisocyanates. The crosslinking reactions of the polyols with polyisocyanate could be catalyzed by the tertiary amine groups included in the polyols, and the reaction rate was affected by hydrochloric acid and the polarity of the solvents. The mechanical, water-resistance, and chemical-resistance properties of the crosslinked products of the polyols were evaluated by standard tests, and the thermal properties were examined by differential scanning calorimetry and thermogravimetric analysis. The results show that these epoxyurethane polymers, with glass-transition temperatures (T g 's) in the range À5 to 37 C, had good thermally resistant properties, and the temperatures at 5% weight loss were in the range 235-280 C. All of the polymers formed transparent, strong, flexible films, with good chemical-resistance properties and excellent impact strengths of greater than 50 cm, a flexibility of 0.5 mm, adhesions of 1-2, and pencil hardnesses of HB-2H. The larger OH functionality and OH value of the polyol resulted in higher T g and pencil hardness values and better alcohol resistance and thermal stability in the crosslinked product of the polyol. V
European Polymer Journal, 2007
A new diamine containing ferrocene group with preformed ether and amide units was prepared via reaction of 1,1 0ferrocenedicarbonyl chloride with two moles of 2,6-bis(5-amino-1-naphthoxy)pyridine. Polycondensation reactions of the prepared diamine with different aromatic and aliphatic diacid chlorides in the presence of trimethylchlorosilane (TMSCl) resulted in preparation of novel ferrocene modified poly(amide ether amide)s. The monomer and polyamides were characterized and the effect of trimethylchlorosilane (TMSCl) as activating agent on the polymerization reaction was studied. The physical and thermal properties of the polyamides including inherent viscosity, solubility, thermal stability and behavior, flame-retardancy and crystallinity of the polymers were studied. The polymers showed good thermal stability and flame-retardancy, and also improved solubility in polar aprotic solvents.
Journal of Inorganic and Organometallic Polymers and Materials, 2011
A new ferrocene-based diamine (ESAFDA) with built-in ether, sulfone, and amide groups was prepared via reaction of two synthetic precursors. Firstly, 1,1 0 -ferrocenedicarbonyl chloride was prepared from 1,1 0 -ferrocenedicarboxylic acid using oxalyl chloride. In another reaction, nucleophilic substitution reaction of 3-aminophenol with bis(4-chlorophenyl sulfone) was used for synthesis of 3,3 0 -(4,4 0 -sulfonyl bis(1,4-phenylene) bis (oxy)) dianiline (SBOD). Finally, the diamine was prepared via nucleophilic reaction of SBOD with 1,1 0 -ferrocenedicarbonyl chloride. The precursors and the diamine were characterized by conventional methods and the diamine was used for preparation of different ferrocene-based poly(ether sulfone amide imide)s through polycondensation with three different dianhydrides. The polymers were characterized by elemental analysis, FTIR and 1 H-NMR spectroscopy. Various properties of the polymers including inherent viscosity, molecular weight, solubility, thermal stability and behavior, flameretardant nature, mechanical properties, and crystallinity were studied. Presence of ferrocene structure in companion to ether, sulfone, and amide units in the backbone of polyimides led to improved solubility of the polymers in polar aprotic solvents and enhanced thermal stability and flameretardant character of polyimides.
Journal of Chemistry, 2013
A new interesting category of higher thermally stable polyazomethines containing ferrocene in the polymers main chain6a–e was synthesized by solution-polycondensation reaction of 1-(m-formylphenyl)-1′-(5-formyl-2-methoxyphenyl)-ferrocene monomer4with different aliphatic and aromatic diamines. A model compound5was synthesized from dialdehyde monomer4with aniline and was characterized by elemental and spectral analyses. The desirable resulting polymers were characterized by elemental and spectral analyses, in addition to solubility measurement using different solvents. The thermal properties of these polymers were evaluated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) measurements. The redox behaviours were studied for the ferrocene polymers in comparison with both the parent ferrocene monomer and the model compound by using cyclic voltammetry (CV).
Journal of Inorganic and Organometallic Polymers and Materials, 2010
In the past decades, a lot of ferrocene (Fc) derivatives have been synthesized and used in many different applications. In addition, Fc-containing polymers have emerged, as an important class of the metal-containing polymers, with unique electrical, magnetic and optical properties and thus much considerable attention has been paid for the application of these polymer systems. These Fc-containing polymers have many different applications such as amperometric biosensors, immunosensors for proteins, DNA and hepatitis B surface antigen (HBsAg) and carbon monoxide sensors and also they can be used for the fabrication of optical logic gates. This paper reviews the recent progress in the synthetic methodologies, functionalization and the applications of Fc-based polymers as well as some Fc derivatives.
2012
A new ferrocene-based poly(azomethine)ester (P) was synthesized via solution polycondensation of 1,1 0di(chlorocarboxyl) ferrocene with a novel preformed 4-((4-(4-(4-hydroxybenzylideneamino)phenoxy) phenylimino)methyl)phenol (SB). The condensation copolymers with good solubility were obtained using commercially available aliphatic (1,3-propan-diol, 1,6-hexan-diol and poly(dimethylsiloxane), hydroxyl-terminated (n ¼ 550)) and aromatic ((1,1,1,3,3,3-hexaflouro)bisphenol propane and bisphenol A) along with the synthesized monomer (SB) and 1,1 0-di(chlorocarboxyl) ferrocene. The obtained compounds were characterized by elemental analysis, FTIR and 1 H NMR spectrophotometric techniques. The structureeproperty relation was studied in term of solubility measurements, WAXRD and UV evisible spectroscopic techniques. Average molecular weights, M w obtained by laser light scattering method were found to be of the order 10 5 g/mol. Thermogravimetric curves along with polarized optical micrographs were also recorded. SEMeEDX and AFM techniques were employed to study the surface morphology of the synthesized material. Whereas the redox properties were explored using cyclic voltammetric investigations. The biological activity of the synthesized material was studied by utilizing various biological assays (antibacterical, brine shrimp cytotoxicity, antitumor potato disc, DPPH free radical scavenging and free radical induced oxidative DNA damage analysis). In case of brine shrimp (Artemia salina) lethality assay PSi and PF showed LD 50 < 1 ppm indicating highly toxic behavior. PF resulted IC 50 ¼ 37.78 in tumor inhibition assay. The Schiff base (SB) was highly antioxidant with IC 50 ¼ 2.05 ppm and fully protected the plasmid DNA from damage. All the compounds studied were found potent antioxidants, highly cytotoxic and more importantly DNA protecting. The influence of aromatic and aliphatic segments on the properties of organometallic poly(azomethine)ester is discussed.
Journal of Polymer Research, 2016
The thermal, spectroscopic and electrochemical behavior of some novel ferrocene-containing polyesteramides and their siloxane-based block copolymers are described in the present study. The thermal properties of the organometallic materials were investigated by thermogravimetric analysis (TGA) and compared with their terephthaloyl-and isophthaloyl-based organic analogues. The energies of activation of pyrolysis for the polymeric materials were calculated using Horowitz and Metzger method. The spectroscopic and electrochemical properties of the organometallic polymeric materials were examined by means of UV-visible (UV) and cyclic voltammetric (CV) studies. The interactions of these materials with ds.DNA (extracted from chicken blood) were also investigated.