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Synthesis and Polymerization of Cationic bis(cyclopentadienyliron)arene Complexes Containing Arylazo Dyes

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The synthesis of the title complexes was achieved via the reaction of \(\eta^{6}\)-p-dichlorobenzene- \(\eta^{5}\)-cyclopentadienyliron cations with 4,4′-bis(4-hydroxyphenyl)valeric acid to produce the diiron complexes which were then reacted with a number of arylazo dyes to give cationic bis(cyclopentadienyliron)arene complexes containing the arylazo dyes. These iron-containing monomers were subsequently polymerized via nucleophilic aromatic substitution using 1,8-octanedithiol, 4,4′-thiobisbenzenethiol, or bisphenol A to produce the desired coloured cationic organoiron polymers. The weight – average molecular weights were estimated to range from 11,800 to 31,600. UV–vis studies conducted in dimethylformamide (DMF) showed that the metallated polymers exhibited \(\lambda_{\max}\) of 412–491 nm. Addition of HCl to the polymer solution caused a bathochromic shift into the range of 515–530 nm. Thermogravimetric analysis (TGA) revealed that the iron moieties were cleaved between 205 and 248 °C while the polyether/thioether backbone degraded between 380 and 613 °C. Differential scanning calorimetry (DSC) showed that the polymers exhibited glass transition temperatures (Tg) ranging from 106 to 184°C.

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Acknowledgments

Financial support provided by the Natural Sciences Engineering and Research Council of Canada (NSERC) and the University of Winnipeg are gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, The University of Winnipeg, Winnipeg, Manitoba, Canada, R3B 2E9

    Alaa S. Abd-El-Aziz, Nelson M. Pereira, Waleed Boraie, Erin K. Todd, Tarek H. Afifi, Wes R. Budakowski & Ken J. Friesen

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  1. Alaa S. Abd-El-Aziz
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  2. Nelson M. Pereira
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  3. Waleed Boraie
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  4. Erin K. Todd
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  7. Ken J. Friesen
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Correspondence to Alaa S. Abd-El-Aziz.

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This paper is dedicated to Professor Richard J. Puddephatt in recognition of his outstanding contribution to the field of metal-containing polymers.

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Abd-El-Aziz, A.S., Pereira, N.M., Boraie, W. et al. Synthesis and Polymerization of Cationic bis(cyclopentadienyliron)arene Complexes Containing Arylazo Dyes. J Inorg Organomet Polym 15, 497–509 (2005). https://doi.org/10.1007/s10904-006-9004-4

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