Skip to main content
SpringerLink
Log in

Oriented crystallization of xanthine derivatives sublimated on self-assembled monolayers

  • Published:
Korean Journal of Chemical Engineering Aims and scope Submit manuscript

Abstract

The oriented crystallization of caffeine and theobromine on self-assembled monolayers (SAMs) is reported. The SAMs were prepared by reacting 1-decanethiol, 11-mercapto-1-undecanol, or 11-mercaptoundecanoic acid on flat Au surfaces to form methyl, hydroxyl, or carboxylic acid functionalities on the substrates. Crystallization was conducted by sublimating the xanthine alkaloids on the SAMs. X-ray diffraction and morphology observation/simulation were combined to identify the preferred orientation of caffeine and theobromine crystals. Also, the identified crystal orientation was examined through molecular models to understand the nature of the interfacial interactions that direct the nucleation process. CH/π interaction as well as strong hydrogen bonding appeared to act as the specific interactions to control the molecular orientation of caffeine and theobromine in stereochemically determined manners that persisted during the crystallization process. More importantly, the stability of the orientational regulation showed a clear correlation to the cohesiveness of the xanthine molecular layer parallel to the nucleating substrate. We believe this indicates that the structural coherence of the precursors or nuclei of the crystallization is essential to effectively utilize the interfacial interactions in a cooperative manner to firmly control the crystal orientation.

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

Similar content being viewed by others

References

  1. H. A. Lowenstam and S. Weiner, On Biomineralization, Oxford University Press, New York (1989).

    Google Scholar 

  2. S. Weiner and L. Addadi, J. Mater. Chem., 7, 689 (1997).

    Article  CAS  Google Scholar 

  3. M. Sarikaya, C. Tamerler, A. K.Y. Jen, K. Schulten and F. Baneyx, Nat. Mater., 2, 577 (2003).

    Article  CAS  Google Scholar 

  4. X. Li, W.-C. Chang, Y. J. Chao, R. Wang and M. Chang, Nano Lett., 4, 613 (2004).

    Article  CAS  Google Scholar 

  5. J. Aizenberg, A. Tkachenko, S. Weiner, L. Addadi and G. Hendler, Nature, 412, 819 (2001).

    Article  CAS  Google Scholar 

  6. S. Mann, Biomineralization: Principles and concepts in bioinorganic materials chemistry, Oxford University Press, New York (2001).

    Google Scholar 

  7. G. S. Fu, R. Qiu, C. A. Orme, D. E. Morse and J. J. De Yoreo, Adv. Mater., 17, 2578 (2005).

    Google Scholar 

  8. I.W. Kim, M. R. Darragh, C. Orme and J. S. Evans, Cryst. Growth Des., 6, 5 (2006).

    Article  CAS  Google Scholar 

  9. I.W. Kim, J. L. Giocondi, C. Orme, S. Collino and J. S. Evans, Cryst. Growth Des., 4, 1154 (2008).

    Article  Google Scholar 

  10. A. M. Belcher, X. H. Wu, R. J. Christensen, P. K. Hansma, G. D. Stucky and D. E. Morse, Nature, 381, 56 (1996).

    Article  CAS  Google Scholar 

  11. F. F. Amos and J. S. Evans, Biochemistry, 48, 1331 (2009).

    Article  Google Scholar 

  12. S. Weiner and W. Traub, FEBS Lett., 111, 301 (1980).

    Article  Google Scholar 

  13. L. Addadi and S. Weiner, Proc. Natl. Acad. Sci. USA, 82, 4110 (1985).

    Article  CAS  Google Scholar 

  14. C. A. Orme, A. Noy, A. Wierzbicki, M. T. McBride, M. Grantham, H. H. Teng, P. M. Dove and J. J. DeYoreo, Nature, 411, 775 (2001).

    Article  CAS  Google Scholar 

  15. J. Aizenberg, A. J. Black and G. M. Whitesides, J. Am. Chem. Soc., 121, 4500 (1999).

    Article  CAS  Google Scholar 

  16. Y.-J. Han, L. M. Wysocki, M. S. Thanawala, T. Siegrist and J. Aizenberg, Angew. Chem. Int. Ed., 44, 2386 (2005).

    Article  CAS  Google Scholar 

  17. P.W. Carter and M. D. Ward, J. Am. Chem. Soc., 115, 11521 (1993).

    Article  CAS  Google Scholar 

  18. E. I. Givargizov, M. O. Kliya, V. R. Melik-Adamyan, A. I. Grebenko, R. C. DeMattei and R. S. Feigelson, J. Cryst. Growth, 12, 758 (1991).

    Article  Google Scholar 

  19. B. Pokroy, V. F. Chernow and J. Aizenberg, Langmuir, 25, 14002 (2009).

    Article  CAS  Google Scholar 

  20. J. F. Kang, J. Zaccaro, A. Ulman and A. Myerson, Langmuir, 16, 3791 (2000).

    Article  CAS  Google Scholar 

  21. G. R. Desiraju and T. Steiner, The weak hydrogen bond in structural chemistry and biology, Oxford University Press, New York (1999).

    Google Scholar 

  22. T. Steiner and G. Koellner, J. Mol. Biol., 295, 535 (2001).

    Article  Google Scholar 

  23. K. F. Bowes, I. P. Clark, J. M. Cole, M. Gourlay, A.M. E. Grifn, M. F. Mahon, L. Ooi, A.W. Parker, P. R. Raithby, H. A. Sparkes and M. Towrieb, Cryst. Eng. Commun., 7, 259 (2005).

    Google Scholar 

  24. C. A. Bessel, R. F. See, D. L. Jameson, M. R. Churchill and K. J. Takeuchi, J. Chem. Soc., Dalton Trans., 3123 (1992).

  25. K. A. Ford, Y. Ebisuzaki and P. D. Boyle, Acta Cryst., C54, 1980 (1998).

    CAS  Google Scholar 

  26. G. D. Enright, V.V. Terskikh, D.H. Brouwer and J. A. Ripmeester, Cryst. Growth Des., 7, 1406 (2007).

    Article  CAS  Google Scholar 

  27. I.W. Kim, R. E. Robertson and R. Zand, Adv. Mater., 15, 709 (2003).

    Article  CAS  Google Scholar 

  28. Y. Qian, G. Yang, J. Yu, T.A. Jung and G.-Y. Liu, Langmuir, 19, 6056 (2003).

    Article  CAS  Google Scholar 

  29. Y.-C. Yang, T.-Y. Chang and Y.-L. Lee, J. Phys. Chem. C, 111, 4014 (2007).

    Article  CAS  Google Scholar 

  30. S. M. Mendoza, I. Arfaoui, S. Zanarini, F. Paolucci and P. Rudolf, Langmuir, 23, 582 (2007).

    Article  CAS  Google Scholar 

  31. S. Kumar, K. Subramanian, R. Srinivasan, K. Rajagopalan and T. Steiner, J. Mol. Struct., 471, 251 (1998).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemical and Environmental Engineering, Soongsil University, Seoul, 156-743, Korea

    Jihae Chung & Il Won Kim

Authors
  1. Jihae Chung
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Il Won Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Il Won Kim.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chung, J., Kim, I.W. Oriented crystallization of xanthine derivatives sublimated on self-assembled monolayers. Korean J. Chem. Eng. 28, 232–238 (2011). https://doi.org/10.1007/s11814-010-0444-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11814-010-0444-8

Key words

Search

Navigation