Abstract
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′-ferrocenedicarbonyl chloride was prepared from 1,1′-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′-(4,4′-sulfonyl bis(1,4-phenylene) bis (oxy)) dianiline (SBOD). Finally, the diamine was prepared via nucleophilic reaction of SBOD with 1,1′-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 1H-NMR spectroscopy. Various properties of the polymers including inherent viscosity, molecular weight, solubility, thermal stability and behavior, flame-retardant 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 flame-retardant character of polyimides.
Similar content being viewed by others
References
B.M. Culbertson, C.U. Pittman, New monomers and polymers (Plenum, New York, 1984)
P. Stepnicka, Ferrocenes: ligands, materials and biomolecules (Wiley, Chichester, 2008)
C.E. Carraher, J.E. Sheats, C.U. Pittman, Advances in organometallic and inorganic polymer science (Marcel Dekker, New York, 1982)
P. Nguyen, P. Gomez-Elipe, I. Manners, Organometallic polymers with transition metals in the main chain. Chem. Rev. 99, 1515–1548 (1999)
M. Antonietti, C. Goltner, Superstructures of functional colloids: chemistry on the nanometer scale. Angew. Chem. Int. Ed. Engl. 36, 910–928 (1997)
W.A. Amer, L. Wang, A.M. Amin, L. Ma, H. Yu, Recent progress in the synthesis and applications of some ferrocene derivatives and ferrocene-based polymers. J. Inorg. Organomet. Polym. 20, 605–615 (2010)
C. Simionescu, T. Lixandru, L. Tataru, I. Mazilu, M. Vata, Metallocene monomers and polymers. Ferrocenyl and ferrocenylene derivatives. J. Organomet. Chem. 238, 363–381 (1982)
E. Çevik, M. Şenel, M.F. Abasıyanık, Construction of biosensor for determination of galactose with galactose oxidase immobilized on polymeric mediator contains ferrocene. Curr. Appl. Phys. 10, 1313–1316 (2010)
E.W. Neuse, H. Rosenberg, Metallocene polymers (Marcel Dekker, New York, 1970)
W. Schuhmann, Electron-transfer pathways in amperometric biosensors. Ferrocene-modified enzymes entrapped in conducting-polymer layers. Biosens Bioelectron 10, 181–193 (1995)
Z. Zoric, V. Rapic, S. Lisac, M. Jukic, Ferrocene compounds. XXV. Synthesis and characterization of ferrocene-containing oligoamides, their precursors, and analogues. J. Polym. Sci Part A: Polym. Chem. 37, 25–36 (1999)
P. Kannan, S. Senthil, R. Vijayakumar, R. Marimuthu, Synthesis and characterization of liquid crystalline polymers containing aromatic ester mesogen and a nonmesogenic ferrocene unit in the spacer. J. Appl. Polym. Sci. 86, 3494–3501 (2002)
A.S. Abd-El-Aziz, E.K. Todd, R.M. Okasha, T.E. Wood, Novel approach to oligomers and polymers containing neutral and cationic iron moieties within and pendent to their backbones. Macromol. Rapid Commun. 23, 743–748 (2002)
A. Zirakzadeh, R. Schuecker, W. Weissensteiner, Synthesis of chiral, non-racemic ferrocene derivatives by ortho-metallation and partial reductive removal of ortho-directing amino groups. Tetrahedron Asymmetr. 21, 1494–1502 (2010)
R. Gomez Arrayas, J. Adrio, J.C. Carretero, Recent applications of chiral ferrocene ligands in asymmetric catalysis. Angew. Chem. Int. Ed. 45, 7674–7715 (2006)
P.E. Cassidy, Thermally Stable Polymers (Marcel Dekker, New York, 1980)
M.K. Ghosh, K.L. Mittal, Polyimides: fundamentals and applications (Marcel Dekker, New York, 1996)
C.E. Sroog, A.L. Endrey, S.V. Abramo, C.E. Berr, W.M. Edwards, K.L. Olivier, Aromatic polypyromellitimides from aromatic polyamic acids. J. Polym. Sci. Part A: Polym. Chem. 3, 1373–1390 (1965)
R.B. Seymour, Engineering polymer sourcebook (McGraw-Hill, New York, 1990)
A.H. Frazer, High temperature resistant polymers, vol. 17 (Wiley Interscience, New York, 1968)
T. Seckin, I. Özdemir, S. Köytepe, N. Gürbüz, Preparation and catalytic properties of a Ru(II) coordinated polyimide supported by a ligand containing terpyridine units. J. Inorg. Organomet. Polym. 19, 143–151 (2009)
A.B. Morgan, S. Putthanarat, Use of inorganic materials to enhance thermal stability and flammability behavior of a polyimide. Polym. Degrad. Stab. 96, 23–32 (2011)
D.J. Liaw, P.N. Hsu, B.Y. Liaw, Synthesis and characterization of novel polyamide-imides containing noncoplanar 2,2′-dimethyl-4,4′-biphenylene unit. J. Polym. Sci. Part A: Polym. Chem. 39, 63–70 (2001)
J.M. García, J.C. Álvarez, J.G. De La Campa, J. De Abajo, Thermal behavior of aliphatic–aromatic poly(ether-amide)s. J. Appl. Polym. Sci. 67, 975–981 (1998)
S. Mehdipour-Ataei, S. Saidi, Structure–property relationships of low dielectric constant, nanoporous, thermally stable polyimides via grafting of poly(propylene glycol) oligomers. Polym. Adv. Technol. 19, 889–894 (2008)
S. Mehdipour-Ataei, N. Bahri-Laleh, A. Amirshaghaghi, Comparison of one-step and two-step method of polyimidization and substitution effect in the synthesis of new poly(ester-imide)s with bulky pendent group. Polym. Degrad. Stab. 91, 2622–2631 (2006)
S. Mehdipour-Ataei, N. Bahri-Laleh, Synthesis and properties of polyimides and copolyimides containing pyridine units: a review. Iran. Polym. J. 17, 95–124 (2008)
S. Babanzadeh, A.R. Mahjoub, S. Mehdipour-Ataei, Novel soluble thermally stable silane-containing aromatic polyimides with reduced dielectric constant. Polym. Degrad. Stab. 95, 2492–2498 (2010)
A. Rabiee, S. Mehdipour-Ataei, Physical and mechanical properties of sulfonated aromatic copolyimide membranes. e-Polymers 110, 1–10 (2009)
S. Mehdipour-Ataei, F. Taremi, Preparation and properties of novel thermally stable pyridine-based poly(amide imide amide)s. J. Appl. Polym. Sci. 121, 299–308 (2011)
M.M. Abd-Alla, M.F. El-Zohry, K.I. Aly, M.M. Abd-El-Wahab, Arylidene polymers. XVIII. Synthesis and thermal behavior of organometallic arylidene polyesters containing ferrocene derivatives in the main chain. J. Appl. Polym. Sci. 47, 323–329 (1993)
S. Mehdipour-Ataei, S. Babanzadeh, New types of heat-resistant, flame-retardant ferrocene-based polyamides with improved solubility. React. Func. Polym. 67, 883–892 (2007)
D.W. Van Krevelen, Some basic aspects of flame resistance of polymeric materials. Polymer 16, 615–620 (1975)
Annual Book of ASTM Standards, D 2863-00 (2000)
S. Mehdipour-Ataei, A. Tadjarodi, S. Babanzadeh, Novel ferrocene modified poly(amide ether amide)s and investigation of physical and thermal properties. Eur. Polym. J. 43, 498–506 (2007)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ebadi-Dehaghani, H., Mehdipour-Ataei, S. Novel Ferrocene-Based Organometallic Poly(ether sulfone amide imide)s: Preparation, Characterization, and Properties. J Inorg Organomet Polym 22, 223–234 (2012). https://doi.org/10.1007/s10904-011-9555-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10904-011-9555-x