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Synthesis of some azacrown derivatives and fabrication of their nanofilms on the glassy carbon surface

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Abstract

The modification of N-phenyl-aza-15-crown-5 (PA15C5) and N-(4-aminophenyl)-aza-15-crown-5 (4APA15C5) on glassy carbon (GC) electrode was performed by the electrochemical oxidation of the corresponding azacrown derivatives in anhydrous acetonitrile media. The electrochemical behavior of the resulting modified GC electrode was investigated in the presence of electroactive redox probes and these results, together with the X-ray photoelectron spectroscopy (XPS) and reflection-absorption infrared spectroscopy were used to confirm the attachment of these molecules onto the GC surface. The ellipsometric thicknesses of PA15C5 and 4APA15C5 films at the GC surface was obtained around 9.28 ± 0.40 and 10.50 ± 1.10 nm, respectively. Azacrown modified nanoscale surfaces serve as alkali metal sensor specific for their cavity in the crown ring.

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References

  1. Costero AM, Sanchis J, Peransi S, Gil S, Sanz V, Domenech A (2004) Tetrahedron 60:4683–4691

    Article  CAS  Google Scholar 

  2. Mashraqui SH, Sundaram S, Khana T, Bhasikuttan AC (2007) Tetrahedron 63:11093–11100

    Article  CAS  Google Scholar 

  3. Rounaghi GH, Razavipanah E (2008) J Incl Phenom Macrocycl Chem 61:313–318

    Article  CAS  Google Scholar 

  4. Gromov SP, Dmitrieva SN, Churakova MV, Vedernikov AI, Kurchavov NA, Kuzmina LG, Kataeva NA, Hovard JAK (2004) Russ J Org Chem 40:1200–1209

    Article  CAS  Google Scholar 

  5. Mashraqui SH, Sundaram S, Khan T, Ghadigaonkar S, Poonia K (2008) J Incl Phenom Macrocycl Chem 62:81–90

    Article  CAS  Google Scholar 

  6. Mortimer RJ, Weightman JS (1996) J Electroanal Chem 418:1–7

    Article  CAS  Google Scholar 

  7. Beer PD, Kocian O, Mortimer RJ, Ridgway C, Stradiotto NR (1996) J Electroanal Chem 408:61–66

    Article  Google Scholar 

  8. Beer PD, Blackburn TC, McAleer JF, Sikanyikat H (1990) Inorg Chem 29:378–381

    Article  CAS  Google Scholar 

  9. Wang J (2008) Chem Rev 108:814–825

    Article  CAS  Google Scholar 

  10. Zen JM, Kumar AS, Tsai DM (2003) Electroanal 15:1073–1087

    Article  CAS  Google Scholar 

  11. Downard AJ, Tan ESQ, Yu SSC (2006) New J Chem 30:1283–1288

    Article  CAS  Google Scholar 

  12. Jin GP, Lin XQ, Gong JM (2004) J Electroanal Chem 569:135–142

    Article  CAS  Google Scholar 

  13. Mills N (2004) J Am Chem Soc 128:13649–13650

    Article  Google Scholar 

  14. Cui Y, Qian G, Chen L, Wang Z, Gao J, Wang M (2006) J Phys Chem B 110:4105–4110

    Article  CAS  Google Scholar 

  15. Vladimirova MP, Simova SD, Stanoeva ER, Mitewa MI (2001) Dye Pigment 50:157–162

    Article  CAS  Google Scholar 

  16. Lu XX, Qin SY, Zhou ZY, Yam VWW (2003) Inorg Chim Acta 346:49–56

    Article  CAS  Google Scholar 

  17. Dix JP, Vögtle F (1980) Chem Ber 113:457–470

    Article  CAS  Google Scholar 

  18. Taner B, Özcan E, Üstündağ Z, Keskin S, Solak AO, Ekşi H (2010) Thin Solid Films 519:289–295

    Article  CAS  Google Scholar 

  19. Deveci P, Taner B, Üstündağ Z, Özcan E, Solak AO, Kılıç Z (2010) J Mol Struct 982:162–168

    Article  CAS  Google Scholar 

  20. İsbir-Turan AA, Üstündağ Z, Solak AO, Kılıç E, Avseven A (2008) Electroanal 20:1665–1670

    Article  Google Scholar 

  21. Cruickshank AC, Tan ESQ, Brooksby PA, Downard AJ (2007) Electrochem Commun 9:1456–1462

    Article  CAS  Google Scholar 

  22. He JB, Jin GP, Chen QZ, Wang Y (2007) Anal Chim Acta 585:337–343

    Article  CAS  Google Scholar 

  23. Sawyer DT, Sobkowlak A, Julian L, Roberts J (1995) Electrochemistry for chemists, 2nd edn. Wiley-Interscience Pub, New York

    Google Scholar 

  24. Downard AJ (2000) Electroanal 12:1085–1096

    Article  CAS  Google Scholar 

  25. İsbir-Turan AA, Üstündağ Z, Solak AO, Kılıç E, Avseven A (2009) Thin Solid Films 517:2871–2877

    Article  Google Scholar 

  26. Üstündağ Z, İsbir Turan AA, Solak AO, Kılıç E, Avseven A (2009) Instrum Sci Technol 37:284–302

    Article  Google Scholar 

  27. Bekyarova E, Itkis ME, Ramesh P, Berger C, Sprinkle M, Heer WA, Haddon RC (2009) J Am Chem Soc 131:1336–1337

    Article  CAS  Google Scholar 

  28. Üstündağ Z, Solak AO (2009) Electrochim Acta 54:6426–6432

    Article  Google Scholar 

  29. Montagne F, Polesel-Maris J, Pugin R, Heinzelmann H (2009) Langmuir 25:983–991

    Article  CAS  Google Scholar 

  30. Schlapak R, Pammer P, Armitage D, Zhu R, Hinterdorfer P, Vaupel M, Frhwirth T, Howorka S (2006) Langmuir 22:277–285

    Article  CAS  Google Scholar 

  31. Yang G, Liu B, Dong S (2005) J Electroanal Chem 585:301–305

    Article  CAS  Google Scholar 

  32. Uchiyama S, Watanabe H, Yamazaki H, Kanazawa A, Hamana H, Okabe Y (2007) J Electrochem Soc 154:F31–F35

    Article  CAS  Google Scholar 

  33. Liu J, Cheng L, Liu B, Dong S (2000) Langmuir 16:7471–7476

    Article  CAS  Google Scholar 

  34. Saby C, Ortiz B, Champagne GY, Bélanger D (1997) Langmuir 13:6805–6813

    Article  CAS  Google Scholar 

  35. Adenier A, Bernard MC, Chehimi MM, Deliry EC, Desbat B, Fagebaume O, Pinson J, Podvorica F (2001) J Am Chem Soc 123:4541–4549

    Article  CAS  Google Scholar 

  36. Ray KG III, McCreery RL (1999) J Electroanal Chem 469:150–158

    Article  CAS  Google Scholar 

  37. Lyskawa J, Bélanger D (2006) Chem Mater 18:4755–4763

    Article  CAS  Google Scholar 

  38. Silverstein RM, Webster FX (1998) Spectroscopic identification of organic compounds. Wiley, New York

    Google Scholar 

  39. Attard G, Barnes C (1998) Surfaces, Oxford chemistry primers. Oxford Science Publications, Oxford

    Google Scholar 

  40. Poksinski M, Arwin H (2004) Thin Solid Films 455:716–721

    Article  Google Scholar 

  41. Demirel G, Ağlayan C, Garipcan M, Duman BO, Pişkin M (2007) Nanoscale Res Lett 2:350–354

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by TUBITAK (Scientific and Technological Research Council of Turkey) with project the numbers of 108T655 and 106T622 and the Research Fund of Selcuk University (project number: 08101030) under thesis. It was also supported by the Ankara University Scientific Research Fund with the project grant number of 09B4240012. The authors thank Dr. Selda Keskin from Middle East Technical University (Ankara) for acquiring the XPS spectra.

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Correspondence to Emine Özcan.

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Deveci, P., Taner, B., Üstündağ, Z. et al. Synthesis of some azacrown derivatives and fabrication of their nanofilms on the glassy carbon surface. J Solid State Electrochem 16, 985–992 (2012). https://doi.org/10.1007/s10008-011-1474-9

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  • DOI: https://doi.org/10.1007/s10008-011-1474-9

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