Skip to main content
SpringerLink
Log in

Selective oxidation of benzyl alcohol on poly(4-(3-(pyrrol-1-yl)propionamido)-2,2,6,6-tetramethylpiperidin-1-yloxy) electrode

  • Original Paper
  • Published:
Journal of Solid State Electrochemistry Aims and scope Submit manuscript

Abstract

The derivative monomer of pyrrole with the side chain nitroxyl radical, 4-(3-(pyrrol-1-yl)propionamido)-2,2,6,6-tetramethylpiperidin-1-yloxy (PyATEMPO) was synthesized. Its corresponding polymer PPyATEMPO was successfully prepared by cyclic voltammetry on Pt electrode in NaClO4/CH3CN solution. The PPyATEMPO electrode showed high electrocatalytic activity for oxidation of benzyl alcohol in the presence of the Lewis base 2,6-lutidine. To further investigation, in situ Fourier transform infrared (FTIR) spectroscopy technique was applied to study the possible electrochemical oxidation mechanism of benzyl alcohol on PPyATEMPO electrode. It showed that the benzyl alcohol was selectively oxidized to benzaldehyde in the action of PPyATEMPO film.

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

Similar content being viewed by others

References

  1. Demizu Y, Shiigi H, Oda T, Matsumura Y, Onomura O (2008) Tetrahedron Lett 49(1):48–52

    Article  CAS  Google Scholar 

  2. Zhan BZ, Thompson A (2004) Tetrahedron 60(13):2917–2935

    Article  CAS  Google Scholar 

  3. Yang GY, Guo YC, Wu GH, Zheng LW, Song MP (2007) Prog Chem 19:1727–1735

    Google Scholar 

  4. Onomura O, Mitsuda M, Nguyen MTT, Demizu Y (2007) Tetrahedron Lett 48(52):9080–9084

    Article  CAS  Google Scholar 

  5. Weickgenannt A, Mewald M, Muesmann TWT, Oestreich M (2010) Angew Chem Int Ed 49(12):2223–2226

    Article  CAS  Google Scholar 

  6. Wills M (2008) Angew Chem Int Ed 47(23):4264–4267

    Article  CAS  Google Scholar 

  7. Semmelhack MF, Chou CS, Cortes DA (1983) J Am Chem Soc 105:4492

    Article  CAS  Google Scholar 

  8. Osa T, Kashiwagi Y, Mukai K, Ohsawa A, Bobbitt JM (1990) Chem Lett 1:75–78

    Article  Google Scholar 

  9. Bobbitt JM, Flores MCL (1988) Heterocycles 27:509–533

    Article  CAS  Google Scholar 

  10. Kishioka SY, Ohki S, Ohsaka T, Tokuda K (1998) J Electroanal Chem 452:179–186

    Article  CAS  Google Scholar 

  11. Su PG, Peng YT (2014) Sensors Actuators B Chem 193:637–643

    Article  CAS  Google Scholar 

  12. Ariyanayagamkumarappa DK, Zhitomirsky I (2012) Synth Met 162:868–872

    Article  CAS  Google Scholar 

  13. Tan Y, Ghandi K (2013) Synth Met 175:183–191

    Article  CAS  Google Scholar 

  14. Lei W, He P, Zhang SS, Dong FQ, Ma YJ (2014) J Power Sources 266:347–352

    Article  CAS  Google Scholar 

  15. Siu T, Yekta S, Yudin AK (2000) J Am Chem Soc 122:11787–11790

    Article  CAS  Google Scholar 

  16. Murtagh JE, McCooey SH, Connon SJ (2005) Chem Commun 2:227–229

    Article  Google Scholar 

  17. Zhou ZY, Wang Q, Lin JL, Tian N, Sun SG (2010) Electrochim Acta 55:7995–7999

    Article  CAS  Google Scholar 

  18. Sun SG, Lin Y (1998) Electrochim Acta 44:1153–1162

    Article  CAS  Google Scholar 

  19. Belgsira EM, Schafer HJ (2001) Electrochem Commun 3(1):32–35

    Article  Google Scholar 

  20. Arrigan DWM, Gray DS (1999) Anal Chim Acta 402(1–2):157–167

    Article  CAS  Google Scholar 

  21. Hsueh CC, Brajtertoth A (1994) Anal Chem 66:2458–2464

    Article  CAS  Google Scholar 

  22. Zhou M, Heinze J (1999) J Phys Chem B 103:8451–8457

    Article  CAS  Google Scholar 

  23. Kishioka SY, Ohsaka T, Tokuda K (2003) Electrochim Acta 48:1589–1594

    Article  CAS  Google Scholar 

  24. Pieta IS, Ishaq M, Wells RPK, Anderson JA (2010) Appl Catal A Gen 390(1–2):127–134

    Article  CAS  Google Scholar 

  25. Timmiati SN, Jalil AA, Triwahyono S, Setiabudi HD, Annuar NHR (2013) Appl Catal A Gen 459:8–16

    Article  CAS  Google Scholar 

  26. Sousa-Aguiar EF, Camorim VLD, Zotin FMZ, Santos RLC (1998) Microporous Mesoporous Mater 25(1–3):25–34

  27. Keresszegi C, Ferri D, Mallat T, Baiker AJ (2005) Phys Chem B 109(2):958–967

    Article  CAS  Google Scholar 

  28. Cinta S, Morari C, Vogel E, Maniu D, Aluas M, Iliescu T, Cozar O, Kiefer W (1999) Vib Spectrosc 19(2):329–334

    Article  CAS  Google Scholar 

  29. Matthäus C, Wheeler RA (2001) Spectrochim Acta A 57(3):521–534

    Article  Google Scholar 

  30. Meier DM, Urakawa A, Baiker A (2009) J Phys Chem C 113(52):21849–21855

    Article  CAS  Google Scholar 

  31. Olgun U, Gülfen M (2013) Dyes Pigments 99(3):1004–1009

    Article  CAS  Google Scholar 

  32. Kurosaki T, Lee KW, Okawara MJ (1972) J Polym Sci A Polym Chem 10:3295

    Article  CAS  Google Scholar 

  33. Lu JJ, Ma JQ, Yi JM, Shen ZL, Zhong YJ, Ma CA, Li MC (2014) Electrochim Acta 130:412–417

    Article  CAS  Google Scholar 

  34. Mathys GI, Truong VT (1997) Synth Met 89:103–109

    Article  CAS  Google Scholar 

  35. Ono T, Tsunoda M, Takahashi S, Obata T, Sone T, Kashiwagi Y (2010) Heterocycles 81:2771–2780

    Article  CAS  Google Scholar 

  36. Guan XH, Chen GH, Shang CJ (2007) Environ Sci 19(4):438–443

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is supported by the National Natural Science Foundations of China (21206147, 21376224) and the Natural Science Foundation of Zhejiang Province (LY12B05001). The financial supports are gratefully acknowledged.

Author information

Authors and Affiliations

  1. Research Center of Analysis and Measurement, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310032, People’s Republic of China

    Jingmiao Yi, Danyang Tang, Dandan Song, Zhenlu Shen & Meichao Li

  2. College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua, 321004, People’s Republic of China

    Xiaohua Wu

Authors
  1. Jingmiao Yi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Danyang Tang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dandan Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiaohua Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zhenlu Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Meichao Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Zhenlu Shen or Meichao Li.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yi, J., Tang, D., Song, D. et al. Selective oxidation of benzyl alcohol on poly(4-(3-(pyrrol-1-yl)propionamido)-2,2,6,6-tetramethylpiperidin-1-yloxy) electrode. J Solid State Electrochem 19, 2291–2297 (2015). https://doi.org/10.1007/s10008-015-2843-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10008-015-2843-6

Keywords

Search

Navigation