Skip to main content
SpringerLink
Log in

The Dipole Mediated Surface Chemistry of p-Benzoquinonemonoimine Zwitterions

  • Original Paper
  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

This article reviews the surface adsorption of p-benzoquinonemonoimine zwitterions from the class of N-alkyldiaminoresorcinones (or 4,6-bis-dialkylaminobenzene-1,3-diones, i.e. C6H2(···NHR)2(···O)2), where R = H, R = C2H5, n-C4H9), on a variety of conducting surfaces. These small molecules with a large electrical dipole exhibit molecular orientation and packing on surfaces depending on the deposition methodology (from solution or from the vapor) as well as the substrate. What is very clear from the investigations of this class of molecules is that inter-molecular interaction is not simply driven by dipolar interactions alone, but frontier orbital symmetry as well. This is illustrated by the reversible adsorption of di-iodobenzene on molecular films of (6Z)-4-(butylamino)-6-(butyliminio)-3-oxocyclohexa-1,4-dien-1-olate C6H2(···NHR)2(···O)2 where R = n-C4H9, where it is clear that absorption is isomer specific.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Zhang Z, Alvira J, Barbosa X, Rosa LG, Routaboul L, Braunstein P, Doudin B, Dowben PA (2011) J Phys Chem C 115:2812–2818

    Article  CAS  Google Scholar 

  2. Topping J (1927) Proc R Soc A 114:67

    Article  Google Scholar 

  3. Levshin NL, Yudin SG, Diankina AP (1997) Mosc Univ Phys Bull (Vestnik Moskovskogo Universiteta Fisika) 52:71–74

    Google Scholar 

  4. Martin B, Vizdrik G, Kliem H (2009) J Appl Phys 105:084114

    Article  Google Scholar 

  5. Rosa LG, Jacobson PA, Dowben PA (2006) J Phys Chem B 2006(110):7944–7950

    Article  Google Scholar 

  6. Dowben PA, Rosa LG, Ilie CC (2008) Z Phys Chem 222:755–778

    Article  CAS  Google Scholar 

  7. Zhang Z, González R, Díaz G, Rosa LG, Ketsman I, Zhang X, Sharma P, Gruverman A, Dowben PA (2011) J Phys Chem C 115:13041–13046

    Article  CAS  Google Scholar 

  8. Yun Y, Altman EI (2007) J Am Chem Soc 129:15684

    Article  CAS  Google Scholar 

  9. Yun Y, Kampschulte L, Liao D, Li M, Altman EI (2007) J Phys Chem C 111:13951

    Article  CAS  Google Scholar 

  10. Garrity K, Kolpak AM, Ismail-Beigi S, Altman EI (2010) Adv Mater 22:2969–2973

    Article  CAS  Google Scholar 

  11. Inoue Y, Yoshioka I, Sato K (1984) J Phys Chem 88:1148–1151

    Article  CAS  Google Scholar 

  12. Inoue Y, Watanabe Y (1993) Catal Today 16:487–494

    Article  CAS  Google Scholar 

  13. Garra J, Vohs JM, Bonnell DA (2009) Surf Sci 603:1106–1114

    Article  CAS  Google Scholar 

  14. Zhao MH, Bonnell DA, Vohs JM (2008) Surf Sci 602:2849–2855

    Article  CAS  Google Scholar 

  15. Zhao MH, Bonnell DA, Vohs JM (2009) Surf Sci 603:284–290

    Article  CAS  Google Scholar 

  16. Burbure NV, Salvador PA, Rohrer GS (2006) J Am Ceram Soc 89:2943

    CAS  Google Scholar 

  17. Giocondi JL, Rohrer GS (2001) Chem Mater 13:241

    Article  CAS  Google Scholar 

  18. Giocondi JL, Rohrer GS (2001) J Phys Chem B 105:8275

    Article  CAS  Google Scholar 

  19. Kalinin SV, Bonnell DA, Alvarez T, Lei X, Hu Z, Ferris JH, Zhang Q, Dunn S (2002) Nano Lett 2:589

    Article  CAS  Google Scholar 

  20. Hanson JN, Rodriguez BJ, Nemanich RJ, Gruverman A (2006) Nanotechnology 17:4946

    Article  CAS  Google Scholar 

  21. Dunn S, Jones PM, Gallardo DE (2007) J Am Chem Soc 129:8724

    Article  CAS  Google Scholar 

  22. Liu X, Kitamura K, Terabe K, Hatano H, Ohashi N (2007) Appl Phys Lett 91:044101

    Article  Google Scholar 

  23. Dunn S, Tiwari D (2008) Appl Phys Lett 93:092905

    Article  Google Scholar 

  24. Dunn S, Cullen D, Abad-Garcia E, Bertoni C, Carter R, Howorth D, Whatmore RW (2004) Appl Phys Lett 85:3537

    Article  CAS  Google Scholar 

  25. Ke C, Wang X, Hu XP, Zhu SN, Qi M (2007) J Appl Phys 101:064107

    Article  Google Scholar 

  26. Habicht S, Nemanich RJ, Gruverman A (2008) Nanotechnology 19:495303

    Article  CAS  Google Scholar 

  27. Haussmann A, Milde P, Erler C, Eng LM (2009) Nano Lett 9:763–768

    Article  CAS  Google Scholar 

  28. Müller M, Soergel E, Buse K (2003) Appl Phys Lett 83:1824

    Article  Google Scholar 

  29. Kunkel DA, Simpson S, Nitz J, Rojas GA, Zurek E, Routaboul L, Doudin B, Braunstein P, Dowben PA, Enders A (2012) Chem Commun 48:7143–7145

    Article  CAS  Google Scholar 

  30. Rojas G, Simpson S, Chen X, Kunkel DA, Nitz J, Xiao J, Dowben PA, Zurek E, Enders A (2012) Phys Chem Chem Phys 14:4971–4976

    Article  CAS  Google Scholar 

  31. Onsager L (1936) J Am Chem Soc 58:1486

    Article  CAS  Google Scholar 

  32. Siri O, Braunstein P (2002) Chem Commun 208–209

  33. Braunstein P, Siri O, Taquet JP, Rohmer MM, Bénard M, Welter R (2003) J Am Chem Soc 125:12246–12256

    Article  CAS  Google Scholar 

  34. Yang QZ, Siri O, Braunstein P (2005) Chem Commun 2660–2662

  35. Xiao J, Zhang Z, Wu D, Routaboul L, Braunstein P, Doudin B, Losovyj YB, Kizilkaya O, Rosa LG, Borca CN, Gruverman A, Dowben PA (2010) Phys Chem Chem Phys 12:10329–10340

    Article  CAS  Google Scholar 

  36. Kong L, Perez Medina GJ, Colón Santana JA, Wong F, Bonilla M, Colón Amill DA, Rosa LG, Routaboul L, Braunstein P, Doudin B, Lee CM, Choi J, Xiao J, Dowben PA (2012) Carbon 50:1981–1986

    Article  CAS  Google Scholar 

  37. Routaboul L, Braunstein P, Xiao J, Zhang Z, Dowben PA, Dalmas G, DaCosta V, Félix O, Decher G, Rosa LG, Doudin B (2012) J Am Chem Soc 134:8494–8506

    Article  CAS  Google Scholar 

  38. Fang Y, Nguyen P, Ivasenko O, Aviles MP, Kebede E, Askari MS, Ottenwaelder X, Ziener U, Siri O, Cuccia LA (2011) Chem Commun 47:11255–11257

    Article  CAS  Google Scholar 

  39. Cahen D, Naaman R, Vager Z (2005) Adv Func Materials 15:1571–1578

    Article  CAS  Google Scholar 

  40. Natan A, Kronik L, Haick H, Tung RT (2007) Adv Mater 19:4103–4117

    Article  CAS  Google Scholar 

  41. Taguchi D, Kajimoto N, Manaka T, Iwamoto M (2007) J Chem Phys 127:044703

    Article  Google Scholar 

  42. Natan A, Zidon Y, Shapira Y, Kronik L (2006) Phys Rev B 73:193310

    Article  Google Scholar 

  43. Yokoyama T, Takahashi T, Shinozaki K, Okamoto M (2007) Phys Rev Lett 98:206102

    Article  Google Scholar 

  44. Barth JV, Brune H, Ertl G, Behm RJ (1990) Phys Rev B 42:9307–9318

    Article  CAS  Google Scholar 

  45. Fukutani K, Wu N, Dowben PA (2009) Surf Sci 603:2964–2971

    Article  CAS  Google Scholar 

  46. Kim BI (2006) Langmuir 22:9272–9280

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research was supported by the National Science Foundation through grants number CHE-0909580, DMR-0747704, DMR-0851703, and the Nebraska EPSCoR grant EPS-1004094, as well as the Centre National de la Recherche Scientifique and the Ministère de la Recherche et des Nouvelles Technologies, the ANR (07-BLAN-0274-04), and the Nebraska Center for Materials and Nanoscience at University of Nebraska-Lincoln. The authors acknowledge the assistance of Zhengzheng Zhang, Jie Xiao, Justin Nitz, Gerson Díaz, Rosette González, Xin Zhang, Lingmei Kong, G. Perez Medina, Juan Colón Santana, Freddy Wong, Manuel Bonilla, Daniel Colón Amill, Guillaume Dalmas and Victor DaCosta. Technical support from the STnano cleanroom facility is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Department of Physics and Astronomy, Nebraska Center for Materials and Nanoscience, University of Nebraska-Lincoln, Theodore Jorgensen Hall, 855 North 16th Street, Lincoln, NE, 68588-0299, USA

    Peter A. Dowben, Donna A. Kunkel, Axel Enders & Luis G. Rosa

  2. Department of Physics and Electronics, University of Puerto Rico-Humacao, Av. Jose E. Aguiar Aramburu Road 908 CUH Station, Humacao, PR, 00791, USA

    Luis G. Rosa

  3. Institute for Functional Nanomaterials, University of Puerto Rico, Facundo Bueso Building, Rio Piedras, PR, 00931, USA

    Luis G. Rosa

  4. Laboratoire de Chimie de Coordination, Institut de Chimie (UMR 7177 CNRS), 4 Rue Blaise Pascal, Université de Strasbourg, 67081, Strasbourg, France

    Lucie Routaboul & Pierre Braunstein

  5. Institut de Physique et Chimie des Matériaux de Strasbourg, IPCMS (UMR 7504), Université Strasbourg, 23 Rue du Lœss, B.P. 20, 67034, Strasbourg, France

    Bernard Doudin

Authors
  1. Peter A. Dowben
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Donna A. Kunkel
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Axel Enders
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Luis G. Rosa
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Lucie Routaboul
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Bernard Doudin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Pierre Braunstein
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Peter A. Dowben.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dowben, P.A., Kunkel, D.A., Enders, A. et al. The Dipole Mediated Surface Chemistry of p-Benzoquinonemonoimine Zwitterions. Top Catal 56, 1096–1103 (2013). https://doi.org/10.1007/s11244-013-0075-5

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11244-013-0075-5

Keywords

Search

Navigation