Bilayer Porphyrin-Graphene Templates for Self-Assembly of Metal-Organic Frameworks on the Surface

E. V. Ermakova,^a Yu. Yu. Enakieva,^a I. N. Meshkov,^a A. E. Baranchikov,^b A. I. Zvyagina,^a Yu. G. Gorbunova,^a,b A. Yu. Tsivadze,^a M. A. Kalinina,^a and V. V. Arslanov^a^@

^aFrumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 119071 Moscow, Russia

^bKurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia

^@Corresponding author E-mail: vladimir.arslanov@gmail.com

DOI: 10.6060/mhc171259a

Macroheterocycles 2017 10(4-5) 496-504

Herein, we describe a new strategy for the formation of bilayer porphyrin-graphene templates to initiate the assembly of various organic or hybrid films including surface metal-organic frameworks on solid substrates. This strategy involves a one-step assembly of a bilayer from the ordered monolayer of functionalized porphyrin and the adsorption layer of graphene oxide at the air-water interface. The behavior of the monolayers of tetrapyridylporphyrin and tetracarboxylphenylporphyrin zinc complexes was studied on the surface of deionized water, aqueous solutions of zinc acetate, graphene oxide and graphene oxide in the presence of zinc acetate. By using a combination of the Langmuir surface method, in situ fiber optic UV-Vis absorption spectroscopy and fluorescence spectroscopy, we determined the molecular organization of the porphyrin films on surface of pure water. The effects of zinc cations and/or the adsorption layer of the graphene oxide on this organization were demonstrated. Strong interactions between the components of the bilayer lead to a substantial shift in the compression isotherms as well as to the quenching of the fluorescence of the porphyrins. The nature of the substituents in the porphyrin structure influences both the structure of the bilayer on the surface of liquid and the morphology of the bilayers transferred onto the solid substrate by the Langmuir-Blodgett technique. The most attractive aspect of our method is a screening of the structure of organic layer from the influence of the underlying solid surface by the GO layer, when the bilayer of tightly bound porphyrin and GO is transferred onto the solid substrate. Because of the specific properties of GO, the resulting bilayer is firmly anchored to the surface, which inhibits desorption of the bilayer material in a course of further bottom-up assembly via Langmuir-Blodgett technique or layer-by-layer assembly. One of the most important advantages of the proposed strategy is the opportunity for creating templates on solid substrates with different nature without use of self-assembled monolayers..

References:

Click here to expand or collapse this section

1. Lüth H. Solid surfaces, interfaces and thin films. Vol. 4. Springer, 2001.
https://doi.org/10.1007/978-3-662-04352-3

2. Sanchez C., Boissière C., Grosso D., Laberty C., Nicole L. Chem. Mater. 2008, 20, 682–737.
https://doi.org/10.1021/cm702100t

3. Jaegermann W., Klein A., Mayer T. Adv. Mater. 2009, 21, 4196–4206.
https://doi.org/10.1002/adma.200802457

4. Gur I., Fromer N.A., Geier M.L., Alivisatos A.P. Science 2005, 310, 462–465.
https://doi.org/10.1126/science.1117908

5. Drisko G.L., Sanchez C. Eur. J. Inorg. Chem. 2012, 2012(32), 5097–5105.
https://doi.org/10.1002/ejic.201201216

6. Sanchez C., Shea K.J., Kitagawa S. Chem. Soc. Rev. 2011, 40, 471–472.
https://doi.org/10.1039/c1cs90001c

7. Descalzo A.B., Martínez‐Má-ez R., Sancenon F., Hoffmann K., Rurack K. Angew. Chem. Int. Ed. 2006, 45, 495–509.
https://doi.org/10.1002/anie.200600734

8. Mendes R.F., Paz F.A.A. Inorg. Chem. Front. 2015, 2, 495–509.
https://doi.org/10.1039/C4QI00222A

9. Long J., Yaghi O. Chem. Soc. Rev. 2009, 38, 1203–1508.
https://doi.org/10.1039/b903811f

10. Férey G. Chem. Soc. Rev. 2008, 37, 191–214.
https://doi.org/10.1039/B618320B

11. Falcaro P., Ricco R., Doherty C.M., Liang K., Hill A.J., Styles M.J. Chem. Soc. Rev. 2014, 43, 5513–5560.
https://doi.org/10.1039/C4CS00089G

12. Peng Y., Li Y., Ban Y., Jin H., Jiao W., Liu X., Yang W. Science 2014, 346, 1356–1359.
https://doi.org/10.1126/science.1254227

13. Liu J., Chen L., Cui H., Zhang J., Zhang L., Su C.-Y. Chem. Soc. Rev. 2014, 43, 6011–6061.
https://doi.org/10.1039/C4CS00094C

14. Li Y.-N., Wang S., Zhou Y., Bai X.-J., Song G.-S., Zhao X.-Y., Wang T.-Q., Qi X., Zhang X.-M., Fu Y. Langmuir 2017, 33, 1060–1065.
https://doi.org/10.1021/acs.langmuir.6b04353

15. Laokroekkiat S., Hara M., Nagano S., Nagao Y. Langmuir 2016, 32, 6648–6655.
https://doi.org/10.1021/acs.langmuir.6b01251

16. Dong L., Gao Z.A., Lin N. Prog. Surf. Sci. 2016, 91, 101–135.
https://doi.org/10.1016/j.progsurf.2016.08.001

17. Stavila V., Talin A.A., Allendorf M. Chem. Soc. Rev. 2014, 43, 5994–6010.
https://doi.org/10.1039/C4CS00096J

18. Decher G. Science 1997, 277, 1232–1237.
https://doi.org/10.1126/science.277.5330.1232

19. Ermakova E., Raitman O., Shokurov A., Kalinina M., Selector S., Tsivadze A., Arslanov V., Meyer M., Bessmertnykh-Lemeune A., Guilard R. Analyst 2016, 141, 1912–1917.
https://doi.org/10.1039/C5AN02523K

20. Arslanov V., Ermakova E., Michalak J., Bessmertnykh-Lemeune A., Meyer M., Raitman O., Vysotskij V., Guilard R., Tsivadze A. Colloids Surf., A 2015, 483, 193–203.
https://doi.org/10.1016/j.colsurfa.2015.05.016

21. Srisombat L., Jamison A.C., Lee T.R. Colloids Surf., A 2011, 390, 1–19.
https://doi.org/10.1016/j.colsurfa.2011.09.020

22. Seitz O., Fernandes P.G., Tian R., Karnik N., Wen H.-C., Stiegler H., Chapman R.A., Vogel E.M., Chabal Y.J. J. Mater. Chem. 2011, 21, 4384–4392.
https://doi.org/10.1039/c1jm10132c

23. Käfer D., Witte G., Cyganik P., Terfort A., Wöll C. J. Am. Chem. Soc. 2006, 128, 1723–1732.
https://doi.org/10.1021/ja0571592

24. Hermes S., Schröder F., Chelmowski R., Wöll C., Fischer R.A. J. Am. Chem. Soc. 2005, 127, 13744–13745.
https://doi.org/10.1021/ja053523l

25. Petit C., Bandosz T.J. J. Colloid Interface Sci. 2015, 447, 139–151.
https://doi.org/10.1016/j.jcis.2014.08.026

26. Huang X., Zheng B., Liu Z., Tan C., Liu J., Chen B., Li H., Chen J., Zhang X., Fan Z. ACS Nano 2014, 8, 8695–8701.
https://doi.org/10.1021/nn503834u

27. Drain C.M., Varotto A., Radivojevic I. Chem. Rev. 2009, 109, 1630–1658.
https://doi.org/10.1021/cr8002483

28. Baskaran D., Mays J.W., Zhang X.P., Bratcher M.S. J. Am. Chem. Soc. 2005, 127, 6916–6917.
https://doi.org/10.1021/ja0508222

29. Geng J., Ko Y.K., Youn S.C., Kim Y.-H., Kim S.A., Jung D.-H., Jung H.-T. J. Phys. Chem. C 2008, 112, 12264–12271.
https://doi.org/10.1021/jp8037208

30. Geng J., Kong B.-S., Yang S.B., Jung H.-T. Chem. Commun. 2010, 46, 5091–5093.
https://doi.org/10.1039/c001609h

31. Chen Y., Mei T., Chen Y., Wang J., Li J., Fu Y., Dai G., Wang S., Xiong W., Wang X. J. Solid State Electrochem. 2016, 20, 2055–2062.
https://doi.org/10.1007/s10008-016-3214-7

32. Wang Y., Zhang Y., Chen J., Dong Z., Chang X., Zhang Y. Electrochem. 2015, 83, 950–955.
https://doi.org/10.5796/electrochemistry.83.950

33. Ge R., Li X., Kang S.-Z., Qin L., Li G. Appl. Catal., B 2016, 187, 67–74.
https://doi.org/10.1016/j.apcatb.2016.01.024

34. Zhu M., Li Z., Xiao B., Lu Y., Du Y., Yang P., Wang X. ACS Appl. Mater. Interfaces 2013, 5, 1732–1740.
https://doi.org/10.1021/am302912v

35. Karousis N., Sandanayaka A.S., Hasobe T., Economopoulos S.P., Sarantopoulou E., Tagmatarchis N. J. Mater. Chem. 2011, 21, 109–117.
https://doi.org/10.1039/C0JM00991A

36. Cárdenas-Jirón G., Borges-Martínez M., Sikorski E., Baruah T. J. Phys. Chem. C 2017, 121, 4859–4872.
https://doi.org/10.1021/acs.jpcc.6b12452

37. Koenig S.P., Boddeti N.G., Dunn M.L., Bunch J.S. Nat. Nanotech. 2011, 6, 543–546.
https://doi.org/10.1038/nnano.2011.123

38. Zong Z., Chen C.-L., Dokmeci M.R., Wan K.-t. AIP 2010.

39. Bunch J.S., Dunn M.L. Solid State Commun. 2012, 152, 1359–1364.
https://doi.org/10.1016/j.ssc.2012.04.029

40. Chen F., Liu S., Shen J., Wei L., Liu A., Chan-Park M.B., Chen Y. Langmuir 2011, 27, 9174–9181.
https://doi.org/10.1021/la201230k

41. Gan S., Zhong L., Wu T., Han D., Zhang J., Ulstrup J., Chi Q., Niu L. Adv. Mater. 2012, 24, 3958–3964.
https://doi.org/10.1002/adma.201201098

42. Wei L., Chen F., Wang H., Zeng T.H., Wang Q., Chen Y. Chem. Asian J. 2013, 8, 437–443.
https://doi.org/10.1002/asia.201200921

43. Kim J., Cote L.J., Kim F., Yuan W., Shull K.R., Huang J. J. Am. Chem. Soc. 2010, 132, 8180–8186.
https://doi.org/10.1021/ja102777p

44. Jia B., Zou L. Chem. Phys. Lett. 2013, 568, 101–105.
https://doi.org/10.1016/j.cplett.2013.02.073

45. Tsujii K. Surface Activity: Principles, Phenomena, and Applications. Academic Press, 1998.

46. Durbut P., Phase A.S.M.I.A. Surfactant Science Series 1999, 47–98.

47. Adler A.D., Longo F.R., Kampas F., Kim J. J. Inorg. Nucl. Chem. 1970, 32, 2443–2445.
https://doi.org/10.1016/0022-1902(70)80535-8

48. Pavinatto F.J., Gameiro A., Hidalgo A., Dinelli L., Romualdo L., Batista A., Neto N.B., Ferreira M., Oliveira O. Appl. Surf. Sci. 2008, 254, 5946–5952.
https://doi.org/10.1016/j.apsusc.2008.03.162

49. Ermakova E.V., Meshkov I.N., Enakieva Y.Y., Zvyagina A.I., Ezhov A.A., Mikhaylov A.A., Gorbunova Y.G., Chernyshev V.V., Kalinina M.A., Arslanov V.V. Surf. Sci. 2017, 660, 39–46.
https://doi.org/10.1016/j.susc.2017.02.007

50. Ermakova E., Enakieva Y.Y., Zvyagina A., Gorbunova Y.G., Kalinina M., Arslanov V. Macroheterocycles 2016, 9, 378–386.
https://doi.org/10.6060/mhc161177a

51. Sakuma T., Sakai H., Araki Y., Wada T., Hasobe T. Phys. Chem. Chem. Phys. 2016, 18, 5453–5463.
https://doi.org/10.1039/C5CP07110K

52. Qiu Y., Chen P., Liu M. J. Am. Chem. Soc. 2010, 132, 9644–9652.
https://doi.org/10.1021/ja1001967

53. Guo P., Chen P., Liu M. ACS Appl. Mater. Interfaces 2013, 5, 5336–5345.
https://doi.org/10.1021/am401260n

54. Van Esch J., Feiters M., Peters A., Nolte R. J. Phys. Chem. 1994, 98, 5541–5551.
https://doi.org/10.1021/j100072a022

55. Xu Y., Liu Z., Zhang X., Wang Y., Tian J., Huang Y., Ma Y., Zhang X., Chen Y. Adv. Mater. 2009, 21, 1275–1279.
https://doi.org/10.1002/adma.200801617

56. Krishna M.B.M., Venkatramaiah N., Venkatesan R., Rao D.N. J. Mater. Chem. 2012, 22, 3059–3068.
https://doi.org/10.1039/c1jm14822b

Attachment	Size
mhc171259a.pdf	3.55 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Bilayer Porphyrin-Graphene Templates for Self-Assembly of Metal-Organic Frameworks on the Surface

References: