Pentakis-Amidothiacalix[4]arene Stereoisomers: Synthesis and Effect of Central Core Conformation on Their Aggregation Properties

Roman V. Nosov, and Ivan I. Stoikov^@
A.M. Butlerov Chemistry Institute, Kazan Federal University, 420008 Kazan, Russian Federation
^@Corresponding author E-mail: ivan.stoikov@mail.ru

DOI: 10.6060/mhc140929s

Macroheterocycles 2015 8(2) 120-127

New monosubstituted pentakisthiacalix[4]arenes in three different configurations (cone, partial cone and 1,3-alternate) were synthesized and their structure and composition were characterized by a number of physical methods including 1H, 13C, IR spectroscopy and mass spectrometry. The spatial structure was confirmed by two-dimensional 1H-1H NMR spectroscopy. It was shown that nano-sized aggregates with silver cation were formed only in the case of multicalixarene with a cone configuration of the central core.

References:

Click here to expand or collapse this section

1. Guosong C., Jiang M. Chem. Soc. Rev. 2011, 40, 2254–2266.

http://dx.doi.org/10.1039/C0CS00153H

2. Massimo B., Rossi S., Karlsson G., Almgren M., Lo Nostro P., Baglioni P. Langmuir 2006, 4, 1478–1484.

http://dx.doi.org/10.1021/la052878f

3. Ribó J. M., Farrera J.-A., Valero M., Virgili A. Tetrahedron 1995, 12, 3705–3712.

http://dx.doi.org/10.1016/0040-4020(95)00085-M

4. Stoikov I.I., Yushkova E.A., Zhukov A.Y., Zharov I., Antipin I.S., Konovalov A.I. Tetrahedron 2008, 64, 7489–7497.

http://dx.doi.org/10.1016/j.tet.2008.05.102

5. Stoikov I.I., Yushkova E.A., Zharov I., Antipin I.S., Konovalov A.I. Tetrahedron 2009, 65, 7109–7114.

http://dx.doi.org/10.1016/j.tet.2009.06.045

6. Li X., Gong S.L., Yang W.P., Chen Y.Y., Meng X.G. Tetrahedron 2008, 64, 6230–6237.

http://dx.doi.org/10.1016/j.tet.2008.04.116

7. Iki N., Narumi F., Fujimoto T., Morohashi N., Miyano S. J. Chem. Soc., Perkin Trans. 1998, 2, 2745–2750.

http://dx.doi.org/10.1039/a803734e

8. Sándor K.-M., Vasapollo G., Szabó K., Bitter I., Mele G., Longo L., Kollár L. J. Inclusion Phenom. Macrocyclic Chem. 2008, 60, 71–78.

http://dx.doi.org/10.1007/s10847-007-9354-8

9. Lhoták P., Kawaguchi M., Ikeda A., Shinkai S. Tetrahedron 1996, 52, 12399–12408.

http://dx.doi.org/10.1016/0040-4020(96)00738-7

10. Stoikov I.I., Ibragimova D.S., Shestakova N.V., Krivolapov B.D., Litvinov I.A., Antipin I.S., Konovalov A.I., Zharov I. Supramol. Chem. 2009, 21, 564–571.

http://dx.doi.org/10.1080/10610270802438820

11. Mostovaya O., Agafonova M., Galukhin A., Khayrutdinov B., Islamov D., Kataeva O., Antipin I., Konovalov A., Stoikov I.I. J. Phys. Org. Chem. 2014, 27, 57–65.

http://dx.doi.org/10.1002/poc.3236

12. Galukhin A.V., Shabalin K.V., Antipin I.S., Konovalov A.I., Stoikov I.I. Mendeleev Commun. 2013, 23, 41–43.

http://dx.doi.org/10.1016/j.mencom.2013.01.015

13. Galukhin A., Stoikov I. Mendeleev Commun. 2014, 24, 82–84.

http://dx.doi.org/10.1016/j.mencom.2014.03.005

14. Morohashi N., Hattori T., Yokomakura K., Kabuto C., Miyano S. Tetrahedron Lett. 2002, 43, 7769

http://dx.doi.org/10.1016/S0040-4039(02)01833-6

15. Proto A., Giugliano F., Capacchione C. Eur. Polym. J. 2009, 45, 2138–2141.

http://dx.doi.org/10.1016/j.eurpolymj.2009.04.014

16. Baldini L., Cacciapaglia R., Casnati A., Mandolini L., Salvio R., Sansone F., Ungaro R. J. Org. Chem. 2012, 77, 3381−3389.

http://dx.doi.org/10.1021/jo300193y

17. Vavilova A.A., Nosov R.V., Yakimova L.S., Antipin I.S., Stoikov I.I. Macroheterocycles 2013, 3, 219–226.

http://dx.doi.org/10.6060/mhc130748s

18. Vavilova A.A., Nosov R.V., Yagarmina A.N., Mostovaya O.A., Antipin I.S., Konovalov A.I., Stoikov I.I. Macroheterocycles 2012, 5, 396–403.

http://dx.doi.org/10.6060/mhc2012.121105s

19. Stoikov I.I., Yantemirova A.A., Nosov R.V., Julmetov A.R., Klochkov V.V., Antipin I.S., Konovalov A.I. Mendeleev Commun. 2011, 21, 41–43.

http://dx.doi.org/10.1016/j.mencom.2011.01.017

20. Guo D.S., Liu Y. Chem. Soc. Rev. 2012, 41, 5907–5921.

http://dx.doi.org/10.1039/c2cs35075k

21. Guan B., Jiang M., Yang X., Liang Q., Chen Y. Soft Matter 2008, 4, 1393–1395.

http://dx.doi.org/10.1039/b805312j

22. Liang Q., Chen G., Guan B., Jiang M. J. Mater. Chem. 2011, 21, 13262–13267.

http://dx.doi.org/10.1039/c1jm10895f

23. Sun C.Y., Liu S.X., Liang D.D., Shao K.Z., Ren Y.H., Su Z.M. J. Am. Chem. Soc. 2009, 131, 1883–1888.

http://dx.doi.org/10.1021/ja807357r

24. Yushkova E.A., Stoikov I.I. Langmuir 2009, 25, 4919–4928.

http://dx.doi.org/10.1021/la8040902

25. Stoikov I.I., Yushkova E.A., Bukharaev A.A., Biziaev D.A., Ziganshina S.A., Zharov I. J. Phys. Chem., C 2009, 113, 15838–15844.

http://dx.doi.org/10.1021/jp902904n

26. Sameni S., Jeunesse C., Matt D., Harrowfield J. Chem. Soc. Rev. 2009, 38, 2117–2146.

http://dx.doi.org/10.1039/b900183b

27. Lhoták P., Kawaguchi M., Ikeda A., Shinkai S. Tetrahedron 1996, 52, 12399–12408.

http://dx.doi.org/10.1016/0040-4020(96)00738-7

28. McKervey M.A., Pitarch M. Chem. Commun. 1996, 1689–1690.

http://dx.doi.org/10.1039/cc9960001689

29. Pitarch M., McKee V., Nieuwenhuyzen M., McKervey M.A. J. Org. Chem. 1998, 63, 946–951.

http://dx.doi.org/10.1021/jo970887q

30. Chuan-Feng C., Lu L.-G., Hu Z.-Q., Peng X.-X., Huang Z.-T. Tetrahedron 2005, 61, 3853–3858.

http://dx.doi.org/10.1016/j.tet.2005.01.132

31. Galukhin A.V., Andreyko E.A., Rizvanov I.H., Stoikov I.I. Mendeleev Commun. 2013, 23, http://dx.doi.org/10.1016/j.mencom.2013.07.005196–198.

32. Mogck O., Parzuchowski P.M., Nissinen V., Böhmer G.R., Rissanen K. Tetrahedron 1998, 34, 10053-10068.

http://dx.doi.org/10.1016/S0040-4020(98)00594-8

33. Galukhin A.V., Zaikov E.N., Antipin I.S., Konovalov A.I., Stoikov I.I. Macroheterocycles 2012, 5, 266-274.

http://dx.doi.org/10.6060/mhc2012.120781s

34. Green T.W., Wuts P.G. Greene‘s Protective Groups in Organic Synthesis, New York: Wiley-Interscience, 2006. 1110 p.

Attachment	Size
mhc140929s.pdf	1.55 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Pentakis-Amidothiacalix[4]arene Stereoisomers: Synthesis and Effect of Central Core Conformation on Their Aggregation Properties

References: