Compression Speed as a Parameter Changing the Dimensionality of Corrole Nanostructures in Layers at the Air-Water Interface

Thao T. Vu,^a Nadezhda V. Kharitonova,^b Larissa A. Maiorova,^b@ Olga A. Gromova,^c Ivan Yu. Torshin,^d and Oskar I. Koifman^b,e

^aNational University, Hanoi, Vietnam

^bResearch Institute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology, 153000

Ivanovo, Russian Federation

^cIvanovo State Medical Academy, 153000 Ivanovo, Russian Federation

^dInstitute of Modern Information Technologies in Medicine, Federal Research Center “Computer Science and Control” RAS,

119333 Moscow, Russian Federation

^eG.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 153045 Ivanovo, Russian Federation

^@Corresponding author E-mail: Maiorova.Larissa@gmail.com

DOI: 10.6060/mhc171260m
Macroheterocycles 2018 11(3) 286-292

An influence of compression speed of a layer on the structure and properties of stable floating layers of 5,10,15-triphenylcorrol was investigated. Model of face-on monolayers with an increased (by 30 % compared to the quasi-stationary) compression rate has been constructed by method of quantitative analysis of isotherms. It was shown that an increase in the compression speed leads to an increase in the density of both two-dimensional nanoaggregates formed in the layer and the monolayer itself. In addition, there was a significant shift in the boundaries of the existence of floating mono and multilayers in the direction of smaller values of the initial degree of surface coverage.

References:

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1. Islyaikin M.K., Trukhina O.N., Romanenko Y.V., Danilova E.A., Khelevina O.G. Macroheterocycles 2008, 1, 30–39.
https://doi.org/10.6060/mhc2008.1.30

2. Berezin B.D. Coordination Compounds of Porphyrins and Phthalocyanines. Moscow: Nauka, 1978. 280 p. (in Russ.)

3. Satake A., Kobuke Y. Tetrahedron 2005, 61, 13–41.
https://doi.org/10.1016/j.tet.2004.10.073

4. Stuzhin P.A., Ercolani C. Porphyrazines with Annulated Heterocycles. In: The Porphyrin Handbook, Vol. 15 (Kadish K.M., Smith K.M., Guilard R., Eds.) Amsterdam: Academic Press, 2003. p. 263–364.
https://doi.org/10.1016/B978-0-08-092389-5.50011-0

5. Valkova L.A., Borovkov N.Yu., Pisani M., Rustichelli F. Thin Solid Films 2001, 401, 267–272.
https://doi.org/10.1016/s0040-6090(01)01475-4

6. Guldi D.M., Gouloumis A., Vazquez P., Torres T., Georgakilas V., Prato M. J. Am. Chem. Soc. 2005, 127, 5811–5813.
https://doi.org/10.1021/ja043283u

7. Maiorova L.A., Kobayashi N., Zyablov S.V., Bykov V.A., Nesterov S.I., Kozlov A.V., Devillers Ch.H., Zavyalov A.V., Alexandriysky V.V., Orena M., Koifman O.I. Langmuir 2018, 34, 9322–9329.
https://doi.org/10.1021/acs.langmuir.8b00905

8. Konev D.V., Devillers Ch.H., Lizgina K.V., Zyubina T.S., Zyubin A.S., Maiorova-Valkova L.A., Vorotyntsev M.A. Electrochimica Acta 2014, 122, 3 –10.
https://doi.org/10.1016/j.electacta.2013.10.004

9. Snow A.W. Phthalocyanines: Properties and Materials. In: The Porphyrin Handbook, Vol. 17 (Kadish K.M., Smith K.M., Guillard R., Eds.) USA: Elsevier Science, 2003. p. 129–176.
https://doi.org/10.1016/B978-0-08-092391-8.50009-1

10. Paolesse R. Heteroporphyrins, Expanded Porphyrins and Related Macrocycles. In: The Porphyrin Handbook, Vol. 2 (Kadish K.M., Smith K.M., Guilard R., Eds.) New York: Academic Press, 2000. p. 201–232.

11. Paolesse R. Topics in Heterocycl. Chem. 2014, 33, 1–34.
https://doi.org/10.1007/978-3-642-38533-9

12. Expanded, Contracted and Isomeric Porphyrins (Sessler J.L., Weghorn S.J., Eds.), Tetrahedron Org. Chem. Series, Vol. 15 1997, p. 1–520.

13. Erben Ch., Will S., Kadish K.M. Metallocorroles: Molecular Structure, Spectroscopy and Electronic States. In: The Porphyrin Handbook, Vol. 2 (Kadish K.M., Smith K.M., Guilard R., Eds.) New York: Academic Press, 2000. p. 233–300.

14. Aviv I., Gross Z. Chem. Commun. 2007, 20, 1987–1999.
https://doi.org/10.1039/b618482k

15. Paolesse R. Synlett 2008, 15, 2215–2230.
https://doi.org/10.1055/s-2008-1078687

16. Aviv-Harel I., Gross Z. Chem. Eur. J. 2009, 15(34), 8382–8394.
https://doi.org/10.1002/chem.200900920

17. Aviv-Harel I., Gross Z. Coord. Chem. Rev. 2011, 255(7), 717–736.
https://doi.org/10.1016/j.ccr.2010.09.013

18. Karimov D.R. Synthesis, Spectral Characteristics and Reactivity of Corals with Different Types of Functional Substitution. PhD Diss., Ivanovo, 2011. 159 p. (in Russ.).

19. Palmer J.H. Struct. Bond. 2012, 142, 49–90.

20. Liu H.-Y., Mahmood M.HR., Qiu Sh.-X., Chang Ch.K. Coord. Chem. Rev. 2013, 257(7–8), 1306–1333.
https://doi.org/10.1016/j.ccr.2012.12.017

21. Barata J.F.B., Santos C.I.M., Grac M., Nevesa P.M.S., Faustino M.A.F., Cavaleiro J.A.S. Topics in Heterocycl. Chem. 2013, 33, 79–141.
https://doi.org/10.1007/7081_2013_107

22. Thomas K.E., Alemayehu A.B., Conradie J., Beavers CH.M., Ghosh A. Acc. Chem. Res. 2012, 45(8), 1203–1214.
https://doi.org/10.1021/ar200292d

23. Meier-Callahan A.E., Gray H.B., Gross Z. Inorg. Chem. 2000, 39, 3605–3607.
https://doi.org/10.1021/ic000180d

24. Gross Z., Golubkov G., Simkhovich L. Angew. Chem. Int. Ed. 2000, 39, 4045–4047.
https://doi.org/10.1002/1521-3773(20001117)39:22<4045::AID-ANIE4045>3.0.CO;2-P

25. Paolesse R., Natale C.D., Macognano A., Sagone F., Scarselli M.A., Chiaradia P., Troitsky V.I., Berzina T.S., D'Amico A. Langmuir 1999, 15, 1268–1273.
https://doi.org/10.1021/la9712909

26. Gross Z., Simkhovich L., Galili N. Chem. Commun. 1999, 599–600.
https://doi.org/10.1039/a900571d

27. Aviezer D., Cotton S., David M., Segev A., Khaselev N., Galili N., Gross Z., Yayon A. Cancer Res. 2000, 60, 2973–2980.

28. Paolesse R., Pandey R.K., Forsyth T.P., Jaquinod L., Gerzevske K.R., Nurco D.J., Senge M.O., Licoccia S., Boshi T., Smith K.M. J. Am. Chem. Soc. 1996, 118, 3869–3882.
https://doi.org/10.1021/ja9541138

29. Guilard R., Barbe J.M., Stern C., Kadish K.M. Multporphyrins, Multiphthalocyanines and Arrays. In: The Porphyrin Handbook, Vol. 18 (Kadish K.M., Smith K.M., Guilard R., Eds.) Amsterdam: Academic Press, 2003. p. 303–349.
https://doi.org/10.1016/B978-0-08-092392-5.50011-0

30. Mack J., Kobayashi N., Shen Z. The Properties of Porphyrinoids. In: The Porphyrin Handbook, Vol. 2 (Kadish K.M., Smith K.M., Guilard R., Eds.) Singapore: World Scientific, 2013. p. 281–371.

31. Valkova L., Zyablov S., Erokhin V., Koifman O. J. Porphyrins Phthalocyanines 2010, 14, 513–522.
https://doi.org/10.1142/S1088424610002380

32. Valkova L.А., Valli L., Casilli S., Giancane G., Borovkov N.Yu., Sibrina G.V., Glibin A.S., Koifman O.I., Pisani M., Rustichelli F. Langmuir 2008, 24(9), 4857–4864.
https://doi.org/10.1021/la703585p

33. Mishuck E., Eirich F. In: Monomolecular Layers (Sobotka H., Ed.) Washington, DC: American Association for the Advancement of Science, 1954. p. 25.

34. Valkova L.A., Shabyshev L.S., Feigin L.A., Akopova O.B. Molecular Materials 1996, 6(2), 291–298.

35. Valkova L.A., Erokhin V.V., Glibin A.S., Koifman O.I. J. Porphyrins Phthalocyanines 2011, 1044–1051.
https://doi.org/10.1142/S1088424611004026

36. Maiorova L.A. Controlled Self-Assembling of Azaporphyrins in 2D-and 3D-Nanostructures in Langmuir Layers and Langmuir-Blodgett Films. D.Sc. Diss., Ivanovo, 2012. 382 p. (in Russ.).

37. Valkova L.A., Shabyshev L.S., Borovkov N.Yu., Feigin L.A., Rustichelli F. J. Inclusion Phenom. Macrocyclic Chem. 1999, 35, 243-249.
https://doi.org/10.1023/a:1008147031935

38. Valkova L.A., Betrencourt C., Hochapfel A., Myagkov I.V., Feigin L.A. Mol. Cryst. Liq. Cryst. 1996, 287, 269–273.
https://doi.org/10.1080/10587259608038763

39. Valkova L.A., Glibin A.S., Koifman O.I. Macroheterocycles 2011, 4(3), 222–226.
https://doi.org/10.6060/mhc2011.3.13

40. Topchieva I.N., Osipova S.V., Banatskaya M.I., Valkova L.A. Doklady Akademii Nauk SSSR 1989, 308(4), 910–913.

41. Myagkov I.V., Studnev Yu.N. Kolloidn. Zh. 1985, 47, 815–821.

42. Akopova O.B., Bronnikova A.A., Kruvchinskii A., Kotovich L.N., Shabyshev L.S., Valkova L.A. J. Struct. Chem. 1998, 39(3), 376–383.
https://doi.org/10.1007/BF02873645

43. Pisani M., Maiorova L.A., Francescangeli O., Fokin Dm.S., Nikitin K.S., Burmistrov V.A., Kuvshinova S.A., Mengucci P., Koifman O.I. Mol. Cryst. Liq. Cryst. 2017, 649(1), 2–10.
https://doi.org/10.1080/15421406.2017.1303917

44. Karlyuk M.V., Krygin Y.Y., Maiorova L.A., Ageeva T.A., Koifman O.I. Russ. Chem. Bull. 2013, 62, 471–479.
https://doi.org/10.1007/s11172-013-0066-5

45. Vu T.T., Maiorova L.A., Berezin D.B., Koifman O.I. Macroheterocycles 2016, 9(1), 73–79.
https://doi.org/10.6060/mhc151205m

46. Maiorova L.A., Vu T.T., Gromova O.A., Nikitin K.S., Koifman O.I. BioNanoScience 2017, 1(4), 1–9.

47. Valkova L.A., Glibin A.S., Valli L. Colloid J. 2008, 70(1), 6–11.
https://doi.org/10.1134/S1061933X0801002X

48. Paolesse R., Natale C.D., Macagnano A., Sagone F., Scarselli M.A., Chiaradia P. Langmuir 1999, 15, 1268–1274.
https://doi.org/10.1021/la9712909

49. Niu T., Zhang J.L., Chen W. RSC Smart Materials: Supramolecular Materials for Opto-Electronics. (Koch N., Ed.), Vol. 12, GBR, Cambridge: Royal Society of Chemistry, 2014. 98 p.

50. Gao Y., Zhang Y., Ren J., Li D., Gao T., Zhao R., Yang Y., Meng S., Wang C., Liu Z. Nano Research 2012, 5, 543–549.
https://doi.org/10.1007/s12274-012-0239-9

51. Lafferentz L., Eberhardt V., Dri C., Africh C., Comelli G., Esch F., Hecht S., Grill L. Nature Chem. 2012, 4, 215–220.
https://doi.org/10.1038/nchem.1242

52. Song C., Ye R., Bo-Zhong Acta Chim. Sinica – Chinese Editio 2009, 67(17), 2038–2042.

53. Zhang X., Wang Y., Chen P., Rong Y. Minghua Liu Phys. Chem. Chem. Phys. 2016, 18, 14023–14029.
https://doi.org/10.1039/C6CP00683C

54. Crane J.M., Hal S. B. Biophys. J. 2001, 80, 1863–1872.
https://doi.org/10.1016/S0006-3495(01)76156-5

55. Paolesse R., Nardis S., Sagone F., Khoury R.G. J. Org. Chem. 2001, 66(2), 550–556.
https://doi.org/10.1021/jo005661t

56. Koszarna B., Gryko D.T J. Org. Chem. 2006, 71(10), 3707–3717.
https://doi.org/10.1021/jo060007k

57. Maiorova L.A., Koifman O.I., Burmistrov V.A., Kuvshinova S.A., Mamontov A.O. Prot. Met. Phys. Chem. Surf. 2015, 51(1), 85–92.
https://doi.org/10.1134/S2070205115010074

58. Petrova M.V., Maiorova L.A., Gromova O.A., Bulkina T.A., Ageeva T.A., Koifman O.I. Macroheterocycles 2014, 7(3), 267–271.
https://doi.org/10.6060/mhc131163m

59. Vu T.T. Metalporphyrinoids: Stability in Solution and Solid Phase, Features, Electrocatalysis and Thin-Film Materials on their Basis. PhD thesis, Ivanovo, Russia, 2016. 222 p. (in Russ).

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Compression Speed as a Parameter Changing the Dimensionality of Corrole Nanostructures in Layers at the Air-Water Interface

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