Abstract
Poly(1,4-benzoquinonediimine-N,N-diyl-1,4-phenylene) having similar structure to pernigraniline was synthesized by chemical oxidative polymerization of p-phenylenediamine and its salt using potassium peroxydisulfate as an oxidant in molar ratio 1:0.8, in acetic acid, at 278 K. Acetylation of amino end groups of polymers were carried out aiming to prevent self-condensation of amino groups with 1,4-benzoquinone diimine groups by 1,4-addition. Attempting to carry out the reduction of obtained polymer with hydrazine hydrate, it was shown that 1,4-addition of hydrazine to quinonediimine groups occurs instead of expected reduction reaction. When doping obtained polymers with iodine, the electrical conductivity increases up to 10−4 S/cm.
Similar content being viewed by others
References
AIST Database (2018a) Phenylhydrazine. http://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_disp.cgi?sdbsno=561. Accessed 19 Jan 2018
AIST Database (2018b) Hydrazine. http://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_disp.cgi?sdbsno=2784. Accessed 19 Jan 2018
Bellamy LJ (1958) The infra-red spectra of complex molecules. Methuen & Co LTD, London
Cao Y (1990) Spectroscopic studies of acceptor and donor doping of polyaniline in the emeraldine base and pernigraniline forms. Synth Met 35:319–332. https://doi.org/10.1016/0379-6779(90)90216-8
Cataldo F (1996) On the polymerization of p-phenylenediamine. EurPolym J 32:43–50. https://doi.org/10.1016/0014-3057(95)00118-2
Ćirić-Marjanović G, Marjanović B, Bober P, Rozlivková Z, Stejskal J, Trchová M, Prokeš J (2011) The oxidative polymerization of p-phenylenediamine with silver nitrate: towards highly conducting micro/nanostructured silver/conjugated polymer composites. J Polym Sci A Polym Chem 49:3387–3403. https://doi.org/10.1002/pola.24775
de Albuquerque JE, Mattoso LHC, Faria RM, Masters JG, MacDiarmid AG (2004) Study of the interconversion of polyaniline oxidation states by optical absorption spectroscopy. Synth Met 146:1–10. https://doi.org/10.1016/j.synthmet.2004.05.019
Durgaryan AH, Durgaryan NA, ArakelyanRH Matinyan EE (2010) Syntheses and investigation of polymers containing 1-triazene-1,3-diyl and 1,4-phenylene group. Synth Met 160(1–2):180. https://doi.org/10.1016/j.synthmet.2009.10.029
Durgaryan AA, Arakelyan RA, Durgaryan NA (2014) Oxidative polymerization of p-phenylenediamine. Russ J Gen Chem 84:1095–1100. https://doi.org/10.1134/S1070363214060073
Durgaryan AA, Arakelyan RA, DurgaryanNA MartikyanNSh (2017) New method for the synthesis of N, N’-disubstitutedquinonediimine. Russ J Org Chem 53(6):955–958
Ichinohe D, Muranaka T, Sasaki T, Kobayashi M, Kise H (1998) Oxidative polymerization of phenylenediamines catalyzed by horseradish peroxidase, J Polym Sci A 36 pp 2593–2600. 10.1002/(sici)1099-0518(199810)36:14<2593:aid-pola19>3.0.co;2-d
Janošević A, Marjanović B, Rakić A, Ciric-Marjanovic G (2013) Progress in conducting/semiconducting and redox-active oligomers and polymers of arylamines. J Serbian Chem Soc 78:1809–1836. https://doi.org/10.2298/JSC130809097J
Kang ET, Neoh KG, Tan KL (1993) Polyaniline with high intrinsic oxidation state. Surf Interface Anal 20:833–840. https://doi.org/10.1002/sia.740201006
Lakard B, Herlem G, Lakard S, Fahys B (2003) Ab initio study of the polymerization mechanism of poly(p-phenylenediamine). J Mol Struct THEOCHEM 638:177–187. https://doi.org/10.1016/S0166-1280(03)00567-0
Li X-G, Huang M-R, Duan W, Yang Y-L (2002) Novel multifunctional polymers from aromatic diamines by oxidative polymerizations. Chem Rev 102:2925–3030. https://doi.org/10.1021/cr010423z
MacDiarmid AG, Manohar SK, Masters JG, Sun Y, Weiss H, Epstein AJ (1991) Polyaniline: synthesis and properties of pernigraniline base. Synth Met 41:621–626. https://doi.org/10.1016/0379-6779(91)91145-Z
Puzari A, Baruah JB (2001) Oxidative oligomerisation of 1,4-diaminobenzene by copper and cobalt catalysts. React Funct Polym 47:147–152. https://doi.org/10.1016/S1381-5148(01)00024-4
Rawat B, Kansara S, Rama H (1991) Synthesis and study of thermal and electrical behaviour of some polyaromatic amines. Polym Int 26:233–238. https://doi.org/10.1002/pi.4990260406
Sestrem RH, Ferreira DC, Landers R, Temperini MLA, do Nascimento GM (2009) Structure of chemically prepared poly-(para-phenylenediamine) investigated by spectroscopic techniques. Polymer 50:6043–6048. https://doi.org/10.1016/j.polymer.2009.10.028
Stejskal J (2015) Polymers of phenylenediamines. Prog Polym Sci 41:1–31
Trchova M, Stejskal J (2011) Polyaniline: the infrared spectroscopy of conducting polymer nanotubes (IUPAC Technical Report). Pure Appl Chem 83:1803–1817. https://doi.org/10.1351/PAC-REP-10-02-01
Tsuchida E, Kaneko M, Kurimura Y (1970) Oxidative polymerization of aromatic amines in aqueous solution of iron chelate. Makromol Chem 132:209–213. https://doi.org/10.1002/macp.1970.021320119
Vuillard S, Louarn G, Lefrant S, MacDiarmid AG (1994) Vibrational analysis of polyaniline: a comparative study of leucoemeraldine, emeraldine, and pernigraniline bases. Phys Rev B 50(17):12496–12508
Yamamoto T, Nurulla I (1999) Preparation of electrically conducting polyanilines by a new method and electrical conducting properties of the polymers. Jpn J Appl Phys 38(2):L892–L894
Yamamoto T, Nurulla I, Ushiro A (2001) Organometallic C–N coupling between N, N′-dichloro-p-benzoquinone diimine and Grignard reagents and its application to synthesis of polyanilines. Tetrahedron Lett 42:8653–8656
Zeng X-R, Ko T-M (1998) Structures and properties of chemically reduced polyanilines. Polymer (Guildf) 39:1187–1195. https://doi.org/10.1016/S0032-3861(97)00381-9
Acknowledgements
This work was supported by the State Committee of Science MES RA, in frame of the research project No SCS 13-10298.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Miraqyan, N.A., Arakelyan, R.H., Durgaryan, N.A. et al. Synthesis and investigation of poly(p-phenylenediamine)–poly(1,4-benzoquinonediimine-N,N-diyl-1,4-phenylene). Chem. Pap. 72, 1517–1524 (2018). https://doi.org/10.1007/s11696-017-0378-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-017-0378-2