Skip to main content
SpringerLink
Log in

Uncatalyzed synthesis of polypyrrole with viologen side groups and its chemical properties

  • Published:
Journal of Materials Science Aims and scope Submit manuscript

Abstract

A substituted polypyrrole (PPr) with viologen side groups (polymer-1) was obtained from the reaction of N-aminopyrrole with 1-hexyl-1′-(2,4-dinitrophenyl)-4,4′-bipyridinium dihalide (salt-1). A model compound (model-1) was synthesized by the reaction of N-aminopyrrole with N-(2,4-dinitrophenyl)-4-(4-pyridyl)pyridinium chloride (salt-2). UV–vis spectra revealed that polymer-1 had an expanded π-conjugation system along the polymer chain: the polymer showed an onset position of absorption at a wavelength approximately 200 nm longer than the corresponding wavelength of model-1. Polymer-1 received an electrochemical oxidation of the pyrrole ring and reduction of the viologen group within the polymer.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 3

Similar content being viewed by others

References

  1. Maksymiuk K (2006) Electroanal 18:1537

    Article  CAS  Google Scholar 

  2. Geetha S, Rao CRK, Vijayan M, Trivedi DC (2006) Anal Chim Acta 568:119

    Article  CAS  Google Scholar 

  3. Kim BC, Ko JM, Wallace GG (2008) J Power Sources 177:665

    Article  CAS  Google Scholar 

  4. Yamamoto H, Kanemoto K, Oshima M, Isa I (1999) Electrochem 67:855

    Article  CAS  Google Scholar 

  5. Kudoh Y, Kojima T, Fukuyama M, Tsuchiya S, Yoshimura S (1996) J Power Sources 60:157

    Article  CAS  Google Scholar 

  6. Zang J, Li CM, Bao SJ, Cui X, Bao Q, Sun CQ (2008) Macromolecules 41:7053

    Article  CAS  Google Scholar 

  7. Saravanan C, Shekhar RC, Palaniappan S (2006) Macromol Chem Phys 207:342

    Article  CAS  Google Scholar 

  8. Wu AM, Kolla H, Manohar SK (2005) Macromolecules 38:7873

    Article  CAS  Google Scholar 

  9. Sahin Y, Aydin A, Udum YA, Pekmez K, Yildiz A (2004) J Appl Polym Sci 93:526

    Article  CAS  Google Scholar 

  10. Pringle JM, Efthimiadis J, Howlett PC, Efthimiadis J, MacFarlane DR, Chaplin AB, Hall SB, Officer DL, Wallace GG, Forsyth M (2004) Polymer 45:1447

    Article  CAS  Google Scholar 

  11. Ge DT, Wang JX, Wang Z, Wang SC (2002) Synth Met 132:93

    Article  CAS  Google Scholar 

  12. Bazzaoui M, Bazzaoui EA, Martins L, Martins JI (2002) Synth Met 128:103

    Article  CAS  Google Scholar 

  13. Duchet J, Legras R, Demoustier-Champagne S (1998) Synth Met 98:113

    Article  CAS  Google Scholar 

  14. Ishizu K, Tanaka H, Saito R, Maruyama T, Yamamoto T (1996) Polymer 37:863

    Article  CAS  Google Scholar 

  15. An H, Haga Y, Yuguchi T, Yosomiya R (1994) Angew Macromol Chem 218:137

    Article  CAS  Google Scholar 

  16. Nakata M, Shiraishi Y, Taga M, Kise H (1992) Macromol Chem Phys 193:765

    Article  CAS  Google Scholar 

  17. Rapi S, Bocchi V, Gardini GP (1998) Synth Met 24:217

    Article  Google Scholar 

  18. Machida S, Miyata S, Techagumpuch A (1989) Synth Met 31:311

    Article  CAS  Google Scholar 

  19. Hür E, Bereket G, Sahin Y (2006) Mater Chem Phys 100:19

    Article  Google Scholar 

  20. Havinga EE, Hoeve W, Meijer EW, Wynberg H (1989) Chem Mater 1:650

    Article  CAS  Google Scholar 

  21. Bae WJ, Kim KH, Jo WH, Park YH (2005) Macromolecules 38:1044

    Article  CAS  Google Scholar 

  22. Nabid MR, Entezami AA (2004) J Appl Polym Sci 94:254

    Article  CAS  Google Scholar 

  23. Jang KS, Lee H, Moon B (2004) Synth Met 143:289

    Article  CAS  Google Scholar 

  24. Stankovic S, Stankovic R, Ristic M, Pavlovic O, Vojnovic M (1997) React Funct Polym 35:145

    Article  CAS  Google Scholar 

  25. Geckeler KE, Arsalani N, Rivas BL (1997) Macromol Rapid Commun 18:503

    Article  CAS  Google Scholar 

  26. Yamaguchi I, Mizoguchi N, Sato M (2009) Macromolecules 42:4416

    Article  CAS  Google Scholar 

  27. Yamaguchi I, Higashi J, Sato M (2009) J Mater Sci 44:6408. doi:https://doi.org/10.1007/s10853-009-3884-y

    Article  CAS  Google Scholar 

  28. Yamaguchi I, Higashi H, Shigesue S, Shingai S (2007) Tetrahedron Lett 48:7778

    Article  CAS  Google Scholar 

  29. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03, Revision A.1. Gaussian, Inc, Pittsburgh

    Google Scholar 

  30. Yamamoto T (1996) Chem Lett 25:703

    Article  Google Scholar 

  31. Ranger M, Leclerc M (1998) Can J Chem 76:1571

    CAS  Google Scholar 

  32. West K, Bay L, Nielsen MM, Velmurugu Y, Skaarup S (2004) J Phys Chem B 108:15001

    Article  CAS  Google Scholar 

  33. Lacroix JC, Maurel F, Lacaze PC (2001) J Am Chem Soc 123:1989

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Material Science, Faculty of Science and Engineering, Shimane University, 1060 Nishikawatsu, Matsue, 690-8504, Japan

    Isao Yamaguchi & Tomonori Asano

Authors
  1. Isao Yamaguchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tomonori Asano
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Isao Yamaguchi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yamaguchi, I., Asano, T. Uncatalyzed synthesis of polypyrrole with viologen side groups and its chemical properties. J Mater Sci 46, 4582–4587 (2011). https://doi.org/10.1007/s10853-011-5357-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10853-011-5357-3

Keywords

Search

Navigation