Skip to main content
Log in

Layer-by-Layer Assembly of SAM-supported Porphyrin-based Metal Organic Frameworks for Molecular Recognition

  • Published:
Colloid Journal Aims and scope Submit manuscript

Abstract

The development of the sensing systems based on the ultrathin films of functional metal organic networks as efficient synthetic alternative to molecular biosensors is in the focus of intense research. Herein we report how to fabricate uniformly structured surface-attached metal organic frameworks (SURMOFs) from zinc complex of meso-carboxyphenyl-substituted porphyrin and zinc acetate as films on the surface of self-assembled monolayers of silanes and thiols. The layer-by-layer self-assembly with shortened time of the layer deposition at room temperature was applied to obtain 5-layer SURMOFs with high crystallinity, which was confirmed by X-ray diffraction. These SAM-supported SURMOF films were used as sensing layers for qualitative response to organic molecules in aqueous solutions. By using surface plasmon resonance spectroscopy, we showed that the SURMOFs do not bind 4-nitrophenol and uracil whereas they are capable of absorption of purine compounds such as adenine and adenosine 5-monophosphate. This binding is a size sensitive process in favor to adenine suggesting the effect of the SURMOF structure on the molecular recognition. The UV-vis spectroscopy study of the process indicated that the recognition of purines by the porphyrin-based SURMOF proceeds through the interactions of the amine groups with zinc ions in metal clusters rather than with the central metal ions in porphyrin cores. Our findings provide an insight into the sensing properties of the porphyrin-based SURMOFs that is useful for further advancements in fabrication of responsive thin films for biologically relevant analytes.

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

Access this article

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

Instant access to the full article PDF.

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

Similar content being viewed by others

REFERENCES

  1. Love, J.C., Estroff, L.A., Kriebel, J.K., Nuzzo, R.G., and Whitesides, G.M., Chem. Rev., 2005, vol. 105, no. 4, p. 1103.

    Article  CAS  PubMed  Google Scholar 

  2. Ulman, A., Chem. Rev., 1996, vol. 96, no. 4, p. 1533.

    Article  CAS  PubMed  Google Scholar 

  3. Ulman, A., in An Introduction to Ultrathin Organic Films, New York: Academic, 1991, p. 101.

    Google Scholar 

  4. Decher, G., in Multilayer Thin Films, Weinheim: Wiley-VCH, 2012, p. 1.

    Book  Google Scholar 

  5. Richardson, J.J., Cui, J., Bjornmalm, M., Braunger, J.A., Ejima, H., and Caruso, F., Chem. Rev., 2016, vol. 116, no. 23, p. 14828.

    Article  CAS  PubMed  Google Scholar 

  6. Shin, M.J., Shin, Y.J., and Shin, J.S., Colloids Surf. A, 2018, vol. 559, p. 365.

    Article  CAS  Google Scholar 

  7. Mandler, D. and Kraus-Ophir, S., J. Solid State Electrochem., 2011, vol. 15, p. 1535.

    Article  CAS  Google Scholar 

  8. Wink, T., Van Zuilen, S.J., Bult, A., and Van Bennekom, W.P., Analyst, 1997, vol. 122, p. 43.

    Article  Google Scholar 

  9. Arslanov, V., Ermakova, E., Michalak, J., Bessmertnykh-Lemeune, A., Meyer, M., Raitman, O., Vys-otskij, V., Guilard, R., and Tsivadze, A., Colloids Surf. A, 2015, vol. 483, p. 193.

    Article  CAS  Google Scholar 

  10. Chu, B.W.-K. and Yam, V.W.-W., Langmuir, 2006, vol. 22, p. 7437.

    Article  CAS  PubMed  Google Scholar 

  11. Ding, L. and Fang, Y., Chem. Soc. Rev., 2010, vol. 39, p. 4258.

    Article  CAS  PubMed  Google Scholar 

  12. Xie, G., Sun, P., Yan, X., Du, X., and Jiang, Y., Sens. Actuators B, 2010, vol. 145, p. 373.

    Article  CAS  Google Scholar 

  13. Ermakova, E., Raitman, O., Shokurov, A., Kalinina, M., Selector, S., Tsivadze, A., Arslanov, V., Meyer, M., Bessmertnykh-Lemeune, A., and Guilard, R., Analyst, 2016, vol. 141, p. 1912.

    Article  CAS  PubMed  Google Scholar 

  14. Martins, G.F., Pereira, A.A., Stracçalano, B.A., Antunes, P.A., Pasquini, D., Curvelo, A.A.S., Ferreira, M., Riul, A., and Constatino, C.J.L., Sens. Actuators B, 2008, vol. 129, p. 525.

    Article  CAS  Google Scholar 

  15. Zhang, S., Cardona, C.M., and Echegoyen, L., Chem. Commun., 2006, p. 4461.

  16. Zhi, F., Lu, X., Yang, J., Wang, X., Shang, H., Zhang, S., and Xue, Z., J. Phys. Chem. C, 2009, vol. 113, p. 13166.

    Article  CAS  Google Scholar 

  17. Çapan, R., Özbek, Z., Göktaş, H., Şen, S., İnce, F.G., Özel, M.E., Stanciu, G.A., and Davis, F., Sens. Actuators B, 2010, vol. 148, p. 358.

  18. Caseli, L., Moraes, M.L., Zucolotto, V., Ferreira, M., Nobre, T.M., Zaniquelli, M.E.D., Rodrigues Filho, U.P., and Oliveira, O.N., Langmuir, 2006, vol. 22, p. 8501.

    Article  CAS  PubMed  Google Scholar 

  19. Mohammed, M.-I. and Desmulliez, M.P.Y., Lab Chip, 2011, vol. 11, p. 569.

    Article  CAS  PubMed  Google Scholar 

  20. Choi, S., Goryll, M., Sin, L.Y.M., Wong, P.K., and Chae, J., Microfluid. Nanofluidics, 2011, vol. 10, p. 231.

    Article  CAS  PubMed  Google Scholar 

  21. Heinke, L., Gliemann, H., Tremouilhac, P., and Wöll, C., in The Chemistry of Metal-Organic Frameworks: Synthesis, Characterization, and Applications, Kaskel, S., Ed., Weinheim: Wiley-VCH, 2016, p. 523.

  22. Liu, J. and Wöll, C., Chem. Soc. Rev., 2017, vol. 46, p. 5730.

    Article  CAS  PubMed  Google Scholar 

  23. Heinke, L., Tu, M., Wannapaiboon, S., Fischer, R.A., and Wöll, C., Micropor. Mesopor. Mater., 2015, vol. 216, p. 200.

    Article  CAS  Google Scholar 

  24. Liu, J., Zhou, W., Liu, J., Fujimori, Y., Higashino, T., Imahori, H., Jiang, X., Zhao, J., Sakurai, T., Hattori, Y., Matsuda, W., Seki, S., and Wöll, C., J. Mater. Chem. A, 2016, vol. 4, p. 12739.

    Article  CAS  Google Scholar 

  25. Fang, X., Zong, B., and Mao, S., Nano-Micro Lett., 2018, vol. 10, no. 4, p. 64.

    Article  CAS  Google Scholar 

  26. Kreno, L.E., Leong, K., Farha, O.K., Allendorf, M., Van Duyne, R.P., and Hupp, J.T., Chem. Rev., 2012, vol. 112, p. 1105.

    Article  CAS  PubMed  Google Scholar 

  27. Ling, P., Lei, J., Zhang, L., and Ju, H., Anal. Chem., 2015, vol. 87, p. 3957.

    Article  CAS  PubMed  Google Scholar 

  28. Huh, S., Kim, S.-J., and Kim, Y., Cryst. Eng. Commun., 2016, vol. 18, p. 345.

    Article  CAS  Google Scholar 

  29. Chen, Y.-Z. and Jiang, H.-L., Chem. Mater., 2016, vol. 28, p. 6698.

    Article  CAS  Google Scholar 

  30. Li, D.-J., Gu, Z.-G., Vohra, I., Kang, Y., Zhu, Y.-S., and Zhang, J., Small, 2017, vol. 13, p. 1604035.

    Article  CAS  Google Scholar 

  31. Kung, C.-W., Chang, T.-H., Chou, L.-Y., Hupp, J.T., Farha, O.K., and Ho, K.-C., Electrochem. Commun., 2015, vol. 58, p. 51.

    Article  CAS  Google Scholar 

  32. Zhuang, J.-L., Kind, M., Grytz, C.M., Farr, F., Diefenbach, M., Tussupbayev, S., Holthausen, M.C., and Terfort, A., J. Am. Chem. Soc., 2015, vol. 137, p. 8237.

    Article  CAS  PubMed  Google Scholar 

  33. Meshkov, I.N., Zvyagina, A.I., Shiryaev, A.A., Nickolsky, M.S., Baranchikov, A.E., Ezhov, A.A., Nugmanova, A.G., Enakieva, Y.Y., Gorbunova, Y.G., Arslanov, V.V., and Kalinina, M.A., Langmuir, 2018, vol. 34, p. 5184.

    Article  CAS  PubMed  Google Scholar 

  34. Zvyagina, A.I., Shiryaev, A.A., Baranchikov, A.E., Chernyshev, V.V., Enakieva, Y.Y., Raitman, O.A., Ezhov, A.A., Meshkov, I.N., Grishanov, D.A., Ivanova, O.S., Gorbunova, Y.G., Arslanov, V.V., and Kalinina, M.A., New J. Chem., 2017, vol. 41, p. 948.

    Article  CAS  Google Scholar 

  35. Gao, W.-Y., Chrzanowski, M., and Ma, S., Chem. Soc. Rev., 2014, vol. 43, p. 5841.

    Article  CAS  PubMed  Google Scholar 

  36. Ermakova, E.V., Ezhov, A.A., Baranchikov, A.E., Gorbunova, Y.G., Kalinina, M.A., and Arslanov, V.V., J. Colloid Interface Sci., 2018, vol. 530, p. 521.

    Article  CAS  PubMed  Google Scholar 

  37. Makiura, R. and Konovalov, O., Dalton Trans., 2013, vol. 42, p. 15931.

    Article  CAS  PubMed  Google Scholar 

  38. Makiura, R., Motoyama, S., Umemura, Y., Yamanaka, H., Sakata, O., and Kitagawa, H., Nat. Mater., 2010, vol. 9, p. 565.

    Article  CAS  PubMed  Google Scholar 

  39. So, M.C., Jin, S., Son, H.-J., Wiederrecht, G.P., Farha, O.K., and Hupp, J.T., J. Am. Chem. Soc., 2013, vol. 135, p. 15698.

    Article  CAS  PubMed  Google Scholar 

  40. Laokroekkiat, S., Hara, M., Nagano, S., and Nagao, Y., Langmuir, 2016, vol. 32, p. 6648.

    Article  CAS  PubMed  Google Scholar 

  41. Adler, A.D., Longo, F.R., Kampas, F., and Kim, J., J. Inorg. Nucl. Chem., 1970, vol. 32, p. 2443.

    Article  CAS  Google Scholar 

  42. Sun, Y., Yanagisawa, M., Kunimoto, M., Nakamura, M., and Homma, T., Spectrochim. Acta, Part A: Mol. Biomol. Spectrosc., 2017, vol. 184, p. 1.

    Article  CAS  Google Scholar 

  43. Ouerghi, O., Diouani, M.F., Belkacem, A., Elsanousi, A., and Jaffrezic-Renault, N., J. Biomater. Nanobiotechnol., 2016, vol. 7, p. 1.

    Article  CAS  Google Scholar 

  44. Gray, C.H., Trends Biochem. Sci., 1976, vol. 1, p. 142.

    Google Scholar 

  45. So, M.C., Beyzavi, M.H., Sawhney, R., Shekhah, O., Eddaoudi, M., Al-Juaid, S.S., Hupp, J.T., and Farha, O.K., Chem. Commun., 2015, vol. 51, p. 85.

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are grateful to A.E. Baranchikov (IGIC RAS) for a kind assistance with the SEM studies.

X-ray diffraction was performed using the equipment of CKP FMI of IPCE RAS.

Funding

The financial support came from Russian Foundation for Basic Research (grant 16-29-05272_ofi_m) and Ministry of Science and High Education RF.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. A. Kalinina.

Ethics declarations

The authors declare that they have no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kutenina, A.P., Zvyagina, A.I., Raitman, O.A. et al. Layer-by-Layer Assembly of SAM-supported Porphyrin-based Metal Organic Frameworks for Molecular Recognition. Colloid J 81, 401–410 (2019). https://doi.org/10.1134/S1061933X19040070

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1061933X19040070

Navigation