Производные тиакаликс[4]арена по нижнему ободу: синтез и супрамолекулярные свойства

С. Е. Соловьева,^a^,b В. А. Бурилов,^a И. С. Антипин^a^,b^@

^aКазанский федеральный университет, 420008 Казань, Российская Федерация

^bИнститут органической и физической химии Казанского научного центра РАН, 420088 Казань, Российская Федерация

DOI: 10.6060/mhc170512a

Макрогетероциклы 2017 10(2) 134-146

Представлен сводный обзор работ, выполненных в нашей научной группе, по синтезу замещенных по нижнему ободу тиакаликсаренов и их самосборке на мягких поверхностях. Обсуждаются подходы к синтезу различных типов тетра-О-замещенных тиакаликсаренов, полученных в последние 10 лет. Показано, что амфифильные макроциклы в стереоизомерной форме 1,3-альтернат образуют монослои на поверхностях и эффективно встраиваются в везикулы. Нанослои и везикулы, декорированные производными тиакаликсарена, проявляют высокую селективность по отношению к ряду аналитов.

С полным текстом статьи можно ознакомиться на английской версии сайта

References:

Click here to expand or collapse this section

1. Gutsche C.D. Calixarenes Revisited. Monographs in Supramolecular Chemistry. Cambridge: The Royal Society of Chemistry, 1998. 235 p.

2. Gutsche C.D. Calixarenes: an Introduction. 2nd ed. Cambridge: The Royal Society of Chemistry, 2008. 276 p.

3. Calixarenes in Action. (Mandolini L., Ungaro R., Eds.) London: Imperial College Press, 2000. 271 p.

4. Calixarenes 2001. (Asfari Z., Bohmer V., Harrowfield J., Vicens J., Eds.) Netherlands: Kluver, 2001. 683 p.

5. Сalixarenes in Nanoworld. (Vicens J., Harrofield J., Eds.) Netherlands: Springer, 2007. 392 p.

6. Calixarenes and Beyond. (Neri P., Sessler J. L., Wang M.-X., Eds.) Netherlands: Springer, 2016. 1062 p.

7. Kumagai H., Hasegawa M., Miyanari S., Sugawa Y., Sato Y., Hori T., Ueda S., Kamiyama H., Miyano S. Tetrahedron Lett. 1997, 38, 3971–3972.
https://doi.org/10.1016/S0040-4039(97)00792-2

8. Iki N., Miyano S. J. Inclusion Phenom. Macrocycl. Chem. 2001, 41, 99–105.
https://doi.org/10.1023/A:1014406709512

9. Lhotak P. Eur. J. Org. Chem. 2004, 1675–1692.
https://doi.org/10.1002/ejoc.200300492

10. Morohashi N., Narumi F., Iki N., Hattori T., Miyano S. Chem. Rev. 2006, 106, 5291–5316.
https://doi.org/10.1021/cr050565j

11. Agraval Y.K., Pancholi J.P. Indian J. Chem. 2007, 46A, 1372–1382.

12. Konovalov A.I., Antipin I.S. Mendeleev Commun. 2008, 18, 229–237.
https://doi.org/10.1016/j.mencom.2008.09.001

13. Kumar R., Lee Y.O., Bhalla V., Kumar M., Kim J.S. Chem. Soc. Rev. 2014, 43, 4824–4870.
https://doi.org/10.1039/c4cs00068d

14. Yamada M., Rajiv Gandhi M., Kunda U.M.R., Fumio H. J. Inclusion Phenom. Macrocycl. Chem. 2016, 85, 1–18.
https://doi.org/10.1007/s10847-016-0616-1

15. Akdas H., Bringel L., Graf E., Hosseini M.W., Mislin G., Pansanel J., Cian A.D., Fisher J. Tetrahedron Lett. 1998, 39, 2311–2314.
https://doi.org/10.1016/S0040-4039(98)00067-7

16. Kovalenko V.I., Chernova A.V., Borisoglebskaya E.I., Katsyuba S.A., Zverev V.V., Shagidullin R.R., Antipin I.S., Solov"eva S.E., Stoikov I.I., Konovalov A.I. Russ. Chem. Bull. 2002, 51, 825–827.
https://doi.org/10.1023/A:1016084817527

17. Katsyuba S., Kovalenko V., Chernova A., Vandyukova E., Zverev V., Shagidullin R., Antipin I., Solovieva S., Stoikov I., Konovalov A. Org. Biomol. Chem. 2005, 3, 2558–2565.
https://doi.org/10.1039/b504448k

18. Stoikov I.I., Omran O.A., Solovieva S.E., Latypov Sh.K., Enikeev K.M., Gubaidullin A.T., Antipin I.S., Konovalov A.I. Tetrahedron 2003, 59, 1469–1476.
https://doi.org/10.1016/S0040-4020(03)00077-2

19. Solovieva S.E., Grüner M., Omran A.O., Gubaidullin A.T., Litvinov I.A., Habicher W.D., Antipin I.S., Konovalov A.I. Russ. Chem. Bull. 2005, 54, 2104–2112.
https://doi.org/10.1007/s11172-006-0084-7

20. Solovieva S.E., Kleshnina S.R., Kozlova M.N., Galiullina L.F., Gubaidullin A.T., Latypov Sh.K., Antipin I.S., Konovalov A.I. Russ. Chem. Bull. 2008, 57, 1477–1485.
https://doi.org/10.1007/s11172-008-0191-8

21. Tyuftin A.A., Solovieva S.E., Murav’ev A.A., Polyantsev F.M., Latypov Sh.K., Antipin I.S. Russ. Chem. Bull. 2009, 58, 145–151.
https://doi.org/10.1007/s11172-009-0022-6

22. Omran O.A., Antipin I.S. J. Inclusion Phenom. Macrocycl. Chem. 2014, 78, 121–126.
https://doi.org/10.1007/s10847-012-0278-6

23. Stoikov I.I., Galukhin A.V., Zaikov E.N., Antipin I.S. Mendeleev Commun. 2009, 19, 193–195.
https://doi.org/10.1016/j.mencom.2009.07.006

24. Galukhin A.V., Zaikov E.N., Antipin I.S., Konovalov A.I., Stoikov I.I. Macroheterocycles 2012, 5, 266–274.
https://doi.org/10.6060/mhc2012.120781s

25. Kozlova M.N., Ferlay S., Solovieva S.E., Antipin I.S., Konovalov A.I., Kyritsakas N., Hosseini M.W. Dalton Trans. 2007, 5126–5131.
https://doi.org/10.1039/b712351e

26. Kozlova M.N. Molecular tectonics: Nontubular Coordination networks on the thiacalix[4]arene Backbone, PhD thesis. Strasbourg: Univercity Strasbourg, 2008. p. 1–186.

27. Epifanova N.A., Popova E.V., Solovieva S.E., Latypov Sh.K., Antipin I.S., Konovalov A.I. Macroheterocycles 2013, 6, 47–52.
https://doi.org/10.6060/mhc121108s

28. Murav'ev A.A., Galieva F.B., Strel'nik A.G., Nugmanov R.I., Grüner M., Solov'eva S.E., Latypov Sh.K., Antipin I.S., Konovalov A.I. Russ. J. Org. Chem. 2015, 51, 1334–1342.
https://doi.org/10.1134/S1070428015090213

29. Ovsyannikov A., Lang M.N., Ferlay S., Solovieva S.E., Antipin I.S., Konovalov A.I., Kyritsakas N., Hosseini M.W. Dalton Trans. 2013, 42, 116–126.
https://doi.org/10.1039/C2DT31937C

30. Ovsyannikov A., Ferlay S., Solovieva S.E., Antipin I.S., Konovalov A.I., Kyritsakas N., Hosseini M.W. Dalton Trans. 2013, 42, 9946–9953.
https://doi.org/10.1039/c3dt50577d

31. Ovsyannikov A.S., Noamane M.H., Abidi R., Ferlay S., Solovieva S.E., Antipin I.S., Konovalov A.I., Kyritsakas N., Hosseini M.W. Cryst. Eng. Commun. 2016, 18, 691–703.
https://doi.org/10.1039/C5CE02310F

32. Kozlova M.N., Ferlay S., Kyritsakas N., Hosseini M.W., Solovieva S.E., Antipin I.S., Konovalov A.I. Chem. Commun. 2009, 2514–2516.
https://doi.org/10.1039/b902267h

33. Iki N., Narumi F., Fujimoto T., Morohashi N., Miyano S. J. Chem. Soc., Perkin Trans. 2 1998, 2745–2750.
https://doi.org/10.1039/a803734e

34. Akdas H., Mislin G., Graf E., Hosseini M.W., Cian A.D., Fisher J. Tetrahedron Lett. 1999, 40, 2113–2116.
https://doi.org/10.1016/S0040-4039(99)00143-4

35. Lhotak P., Stastny V., Zlatuskova P., Stibor I., Michlova V., Tkadlecova M., Havlicek J., Sykora J. Collect. Czech. Chem. Commun. 2000, 65, 757–771.
https://doi.org/10.1135/cccc20000757

36. Akdas H., Jaunky W., Graf E., Hosseini M.W., Planeix J.M., Cian A.D., Fisher J. Tetrahedron Lett. 2000, 41, 3601–3606.
https://doi.org/10.1016/S0040-4039(00)00453-6

37. Iki N., Narumi F., Suzuki T., Sugawara A., Miyano S. Chem. Lett. 1998, 1065–1066.
https://doi.org/10.1246/cl.1998.1065

38. Muravev A.A., Burilov V.A., Solovieva S.E., Strelґnik A.G., Latypov Sh.K., Bazanova O.B., Sharafutdinova D.R., Antipin I.S., Konovalov A.I. Russ. Chem. Bull. 2014, 63, 214–222.
https://doi.org/10.1007/s11172-014-0416-y

39. Galukhin A.V., Shabalin K.V., Antipin I.S., Konovalov A.I., Stoikov I.I. Mendeleev Commun. 2013, 23, 41–43.
https://doi.org/10.1016/j.mencom.2013.01.015

40. Galukhin A.V., Stoikov I.I. Mendeleev Commun. 2014, 24, 82–84.
https://doi.org/10.1016/j.mencom.2014.03.005

41. Mostovaya O.A., Agafonova M.N., Galukhin A.V., Khayrutdinov B.I., Islamov D., Kataeva O.N., Antipin I.S., Konovalov A.I., Stoikov I.I. J. Phys. Org. Chem. 2014, 27, 57–65.
https://doi.org/10.1002/poc.3236

42. Stoikov I.I., Yushkova E.A., Zhukov A.Yu., Zharov I., Antipin I.S., Konovalov A.I. Tetrahedron 2008, 64, 7489–7497.
https://doi.org/10.1016/j.tet.2008.05.102

43. Stoikov I.I., Yushkova E.A., Zhukov A.Yu., Zharov I., Antipin I.S., Konovalov A.I. Tetrahedron 2008, 64, 7112–7121.
https://doi.org/10.1016/j.tet.2008.05.057

44. Stoikov I.I., Yushkova E.A., Bukharaev A.A., Biziaev D.A., Selivanovskaya S.Yu., Chursina M.A., Antipin I.S., Konovalov A.I., Zharov I. J. Phys. Org. Chem. 2012, 25, 1177–1185.
https://doi.org/10.1002/poc.2981

45. Yushkova E.A., Zaikov E.N., Stoikov I.I., Antipin I.S. Russ. Chem. Bull. 2009, 58, 101–107.
https://doi.org/10.1007/s11172-009-0015-5

46. Zhukov A.Yu., Fink T.A., Stoikov I.I., Antipin I.S. Russ. Chem. Bull. 2009, 58, 1007–1014.
https://doi.org/10.1007/s11172-009-0129-9

47. Stoikov I.I., Zhukov A.Yu., Agafonova M.N., Sitdikov R.R., Antipin I.S., Konovalov A. Tetrahedron 2010, 66, 359–367.
https://doi.org/10.1016/j.tet.2009.10.075

48. Andreyko E.A., Padnya P.L., Stoikov I.I. J. Phys. Org. Chem. 2015, 28, 527–535.
https://doi.org/10.1002/poc.3433

49. Kleshnina S.R., Long N.F., Solov'eva S.E., Antipin I.S., Konovalov A.I. Russ. J. Org. Chem. 2015, 51, 430–435.
https://doi.org/10.1134/S1070428015030240

50. Stoikov I.I., Nasibullin R.Z., Smolentsev V.A., Gafiullina L.I., Zhukov A.Yu., Puplampu J.B., Antipin I.S., Konovalov A.I. Mendeleev Commun. 2006, 16, 248–249.
https://doi.org/10.1070/MC2006v016n05ABEH002377

51. Podyachev S.N., Sudakova S.N., Syakaev V.V., Shagidullin R.R., Galiev A.K., Konovalov A.I. Mendeleev Commun. 2006, 16, 297–299.
https://doi.org/10.1070/MC2006v016n06ABEH002404

52. Stoikov I.I., Yushkova E.A., Zharov I., Antipin I.S., Konovalov A.I. Tetrahedron 2009, 65, 7109–7114.
https://doi.org/10.1016/j.tet.2009.06.045

53. Podyachev S.N., Burmakina N.E., Sudakova S.N., Syakaev V.V., Konovalov A.I. Supramol. Chem. 2010, 22, 339–346.
https://doi.org/10.1080/10610270903531556

54. Yushkova E.A., Stoikov I.I., Zhukov A.Yu., Puplampu J.B., Rizvanov I.Kh., Antipin I.S., Konovalov A.I. RSC Advances 2012, 2, 3906–3919.
https://doi.org/10.1039/c2ra01255c

55. Pod'yachev S.N., Sudakova S.N., Syakaev V.V., Burmakina N.E., Konovalov A.I. Russ. J. Org. Chem. 2010, 46, 1162–1166.
https://doi.org/10.1134/S1070428010080087

56. Podyachev S.N., Barsukova T.A., Bukharov S.V., Syakaev V.V., Sudakova S.N., Nugumanova G.N., Konovalov A.I. Russ. J. Org. Chem. 2012, 48, 1360–1365.
https://doi.org/10.1134/S107042801210017X

57. Rao P., Hosseini M.W., Cian A.D., Fischer J. Chem. Commun. 1999, 2169–2170.
https://doi.org/10.1039/a906058h

58. Katsyuba S.A., Zvereva E.E., Chernova A.V., Shagidullin A.R., Solovieva S.E., Antipin I.S., Konovalov A.I. J. Inclusion Phenom. Macrocycl. Chem. 2008, 60, 281–291.
https://doi.org/10.1007/s10847-007-9376-2

59. Ovsyannikov A.S., Ferlay S., Solovieva S.E., Antipin I.S., Konovalov A.I., Kyritsakas N., Hosseini M.W. Russ. Chem. Bull. 2015, 64, 1955–1962.
https://doi.org/10.1007/s11172-015-1099-8

60. Ovsyannikov A., Ferlay S., Solovieva S.E., Antipin I.S., Konovalov A.I., Kyritsakas N., Hosseini M.W. Inorg. Chem. 2013, 52, 6776−6778.
https://doi.org/10.1021/ic400899m

61. Matsumiya H., Terazono Y., Iki N., Miyano S. J. Chem. Soc., Perkin Trans. 2 2002, 1166–1172.
https://doi.org/10.1039/b200228k

62. Lhotak P., Kaplanek L., Stibor I., Lang J., Dvorakova H., Harbal R., Sykora J. Tetrahedron Lett. 2000, 41, 9339–9344.
https://doi.org/10.1016/S0040-4039(00)01696-8

63. Iki N., Morohashi N.N., Narumi F., Fujimoto T., Suzuki T., Miyano S. Tetrahedron Lett. 1999, 40, 7337–7341.
https://doi.org/10.1016/S0040-4039(99)01503-8

64.Morohashi N., Katagiri H., Iki N., Yamane Y., Kabuto C., Hattori T., Miyano S. J. Org. Chem. 2003, 68, 2324–2333.
https://doi.org/10.1021/jo026801x

65. Bhalla V., Kumar M., Hattori T., Miyano S. Tetrahedron 2004, 60, 5881–5887.
https://doi.org/10.1016/j.tet.2004.05.035

66. Stoikov I.I., Ibragimova D.S., Shestakova N.V., Krivolapov D.B., Litvinov I.A., Antipin I.S., Konovalov A.I., Zharov I. Supramol. Chem. 2009, 21, 564–571.
https://doi.org/10.1080/10610270802438820

67. Bitter I., Csokai V. Tetrahedron Lett. 2003, 44, 2261–2265.
https://doi.org/10.1016/S0040-4039(03)00285-5

68. Burilov V.A., Ibragimova R.R., Nugmanov R.I., Sitdikov R.R., Islamov D.R., Kataeva O.N., Solovieva S.E., Antipin I.S. Russ. Chem. Bull. 2015, 64, 2114–2124.
https://doi.org/10.1007/s11172-015-1126-9

69. Muravev A.A., Solovieva S.E., Latypov Sh.K., Antipin I.S., Konovalov A.I. Phosphorus, Sulfur Silicon Relat. Elem. 2013, 188, 499–502.
https://doi.org/10.1080/10426507.2012.727516

70. Burilov V., Valiyakhmetova A., Mironova D., Safiullin R., Kadirov M., Ivshin K., Kataeva O., Solovieva S., Antipin I. RSC Adv. 2016, 6, 44873–44877.
https://doi.org/10.1039/C6RA07555J

71. Solovieva S.E., Popova E.V., Omran A.O., Gubaidullin A.T., Kharlamov S.V., Latypov Sh.K., Antipin I.S., Konovalov A.I. Russ. Chem. Bull. 2011, 60, 486–498.
https://doi.org/10.1007/s11172-011-0076-0

72. Grootenhuis P.D.J., Kollman P.A., Groenen L.C., Reinhoudt D.N., van Hummel G.J., Ugozzoli F., Andreetti G.D. J. Am. Chem. Soc. 1990, 112, 4165–4176.
https://doi.org/10.1021/ja00167a010

73. Zeng X., Leng X., Chen L., Sun H., Xu F., Li Q., He X., Zhang Z.-Z. J. Chem. Soc., Perkin Trans. 2 2002, 796–801.
https://doi.org/10.1039/b109238c

74. Collins E.M., McKervey M.A., Madigan E., Moran M.B., Owens M., Ferguson G., Harris S.J. J. Chem. Soc., Perkin Trans. 1 1991, 3137–3142.
https://doi.org/10.1039/p19910003137

75. Dvorakova H., Lang J., Vlach J., Sykora J., Cyajan M., Himl M., Pojarova M., Stibor I., Lhotak P. J. Org. Chem. 2007, 72, 7157–7166.
https://doi.org/10.1021/jo070927i

76. Kasyan O. Thondorf I., Bolte M., Kalchenko V., Boehmer V. Acta Cryst. C 2006, C62, o289–o294.
https://doi.org/10.1107/S0108270106011243

77. Dudic M., Lhotak P., Petrickova H., Stibor I., Lang K., Sykora J. Tetrahedron 2003, 59, 2409–2415.
https://doi.org/10.1016/S0040-4020(03)00290-4

78. Bhalla V., Kumar M., Kabuto C., Hattori T., Miyano S. Chem. Lett. 2004, 33, 184–185.
https://doi.org/10.1246/cl.2004.184

79. Van Leeuwen F.W.B., Beijleveld H., Kooijman H., Spek A.L., Verboom W., Reinhoudt D.N. J. Org. Chem. 2004, 69, 3928–3936.
https://doi.org/10.1021/jo0401220

80. Dudic M., Lhotak P., Stibor I., Petrickova H., Lang K. New J. Chem. 2004, 28, 85–90.
https://doi.org/10.1039/B307988K

81. Bhalla V., Kumar M., Katagiri H., Hattori T., Miyano S. Tetrahedron Lett. 2005, 46, 121–124.
https://doi.org/10.1016/j.tetlet.2004.11.008

82. Latypov Sh.K., Kharlamov S.V., Muravev A.A., Balandina A.A., Solovieva S.E., Antipin I.S., Konovalov A.I. J. Phys. Org. Chem. 2013, 26, 407–414.
https://doi.org/10.1002/poc.3101

83. Solovieva S.E., Murav'ev A.A., Latypov Sh.K., Antipin I.S., Konovalov A.I. Dokl. Chem. 2011, 438(2), 170–174.
https://doi.org/10.1134/S0012500811060061

84. Solovieva S.Е., Muravev A.А., Zakirzyanov R.Т., Latypov Sh.К., Antipin I.S., Konovalov A.I. Macroheterocycles 2012, 5(1), 17–22.
https://doi.org/10.6060/mhc2012.111048s

85. Muravev A.A., Solovieva S.E., Kochetkov E.N., Mel'nikova N.B., Safiullin R.A., Kadirov M.K., Latypov Sh.K., Antipin I.S., Konovalov A.I. Macroheterocycles 2013, 6, 302–307.
https://doi.org/10.6060/mhc131269m

86. Muravev A., Galieva F., Bazanova O., Sharafutdinova D., Solovieva S., Antipin I., Konovalov A. Supramol. Chem. 2016, 28, 589–600.
https://doi.org/10.1080/10610278.2016.1150593

87. Burilov V.A., Nugmanov R.I., Ibragimova R.R., Solovieva S.E., Antipin I.S. Mendeleev Commun. 2015, 25, 177–179.
https://doi.org/10.1016/j.mencom.2015.05.005

88. Burilov V.A., Mironova D.A., Ibragimova R.R., Solovieva S.E., Antipin I.S. BioNanoSci. 2016, 6, 427–430.
https://doi.org/10.1007/s12668-016-0255-4

89. Jie K., Zhou Y., Yao Y., Huang F. Chem. Soc. Rev. 2015, 44, 3568–3587.
https://doi.org/10.1039/C4CS00390J

90. Tauran Y., Coleman A.W., Perret F., Kim B. Curr. Org. Chem. 2015, 19, 2250–2270.
https://doi.org/10.2174/1385272819666150608222114

91. Ibragimova R.R., Burilov V.A., Aimetdinov A.R., Mironova D.A., Evtugyn V.G., Osin Y.N., Solovieva S.E., Antipin I.S., Macroheterocycles 2016, 9, 433–441.
https://doi.org/10.6060/mhc161180b

92. Burilov V.A., Mironova D.A., Ibragimova R.R., Nugmanov R.I., Solovieva S.E., Antipin I.S. Colloids Surf., A 2017, 515, 41–49.
https://doi.org/10.1016/j.colsurfa.2016.12.007

93. Mel’nikova N.B., Kochetkov E.N., Solov’eva S.E., Popova E.V., Antipin I.S., Bol’shakova A.E., Zhil’tsova O.E., Konovalov A.I. Russ. Chem. Bull. 2011, 60, 1948–1955.
https://doi.org/10.1007/s11172-011-0294-5

94. Solovieva S.E., Safiullin R.A., Kochetkov E.N., Melnikova N.B., Kadirov M.K., Popova E.V., Antipin I.S., Konovalov A.I. Langmuir 2014, 30, 15153−15161.
https://doi.org/10.1021/la504379v

95. Burilov V.A., Mironova D.A., Ibragimova R.R., Solovieva S.E., Antipin I.S., König B. RSC Adv. 2015, 5, 101177–101185.
https://doi.org/10.1039/C5RA18294H

96. Burilov V.A., Fatikhova G.A., Mironova D.A., Solovieva S.E., Antipin I.S. Macroheterocycles 2015, 8, 409–414.
https://doi.org/10.6060/mhc151087b

Журнал "Макрогетероциклы"

Навигация

Languages

Новости

Поиск

Производные тиакаликс[4]арена по нижнему ободу: синтез и супрамолекулярные свойства

References: