Advertisement

Syntheses and Properties of Crownophanes

  • S. Inokuma
  • M. Ito
  • J. NishimuraEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 17)

Abstract

A variety of crownophanes possessing both crown ether and cyclophane moieties are reviewed and their specific complexation are described. Aromatic nuclei including benzene, naphthalene, anthracene, pyridine, and other condensed polyaromatic rings are dealt with as components of crownophanes. Crownophanes containing nitrogen and sulfur atoms as ligating parts in the tethers of the aromatics are also described. Oxygen-containing crownophanes show high affinity toward alkali and alkaline metal cations with high selectivity. For example, three-bridged crownophane 25 extracted Li+ with excellent selectivity and high efficiency in the competitive system containing Na+ and K+. Four-bridged crownophane 26b showed extraordinarily high selectivity toward Na+ with high efficiency compared with commercially available 15-crown-5 and benzo-15-crown-5. Crownophane 1 having pyridine nuclei as secondary ligating sites on the benzene rings efficiently complexed Ag+ ion with perfect selectivity. Di(p-phenylene) crown 60, 1,5-dinaphtho crown 61, and 1,5-naphtho-p-phenylene crown 62 have been widely employed for donor components of catenanes and rotaxanes. Characteristic behaviors of typical and important crownophanes including above-mentioned ones are summarized in Table 1.

Catenane Crown ether Crownophane Cyclophane Rotaxane  

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Pedersen CJ (1967) J Am Chem Soc 89:7017 CrossRefGoogle Scholar
  2. 2.
    Sutherland IO (1990) In: Gokel GW (ed) Advances in Supermolecular Chemistry, Chap 1. JAI Press, Greenwich, p 65 Google Scholar
  3. 3.
    An H-Y, Bradshaw JS, Izatt RM, Yan Z (1994) Chem Rev 94:939 CrossRefGoogle Scholar
  4. 4.
    Gokel GW (1992) Chem Soc Rev 39:3 Google Scholar
  5. 5.
    Inokuma S, Funaki T, Nishimura J (2002) In: Takemura H (ed) Cyclophanes chemistry for the 21th Century, Chap. 7. Research Signpost, Kerala, India, p 149 Google Scholar
  6. 6.
    Inokuma S, Sakai S, Nishimura J (1994) Top Curr Chem 172:87 CrossRefGoogle Scholar
  7. 7.
    Inokuma S, Yamamoto T, Nishimura (1990) Tetrahedron Lett 31:97 CrossRefGoogle Scholar
  8. 8.
    Inokuma S, Sakai S, Yamamoto T, Nishimura J (1994) J Membr Sci 97:175 CrossRefGoogle Scholar
  9. 9.
    Inokuma S, Gao S-R, Nishimura J (1995) Chem Lett, p 689 Google Scholar
  10. 10.
    Inokuma S, Katoh R, Yamamoto T, Nishimura J (1991) Chem Lett, p 1751 Google Scholar
  11. 11.
    Inokuma S, Saka S, Katoh R, Yasuda T, Nishimura J (1993) Nippon Kagaku Kaishi, p 1148 Google Scholar
  12. 12.
    Inokuma S, Sakai S, Katoh R, Nishimura J (1994) Bull Chem Soc Jpn 67:1462 CrossRefGoogle Scholar
  13. 13.
    Inokuma S, Yasuda T, Araki S, Sakai S, Nishimura J (1994) Chem Lett, p 201 Google Scholar
  14. 14.
    Inokuma S, Kimura K, Funaki T, Nishimura J (2001) Heterocycles 55:447 Google Scholar
  15. 15.
    Inokuma S, Funaki T, Kondo S, Hara D, Nishimura J (2004) Heterocycles 63:333 Google Scholar
  16. 16.
    Mateo C, Pérez-Melero C, Pelaéz R, Medardé M (2005) Tetrahedron Lett 46:7055 CrossRefGoogle Scholar
  17. 17.
    Pigge FC, Ghasedi F, Rath NP (2002) J Org Chem 67:4547 CrossRefGoogle Scholar
  18. 18.
    Pigge FC, Ghasedi F, Schitt AV, Dighe MK, Rath NP (2005) Tetrahedron 61:5363 CrossRefGoogle Scholar
  19. 19.
    Hiratani K, Uzawa H, Kasuga K, Kambayashi H (1997) Tetrahedron Lett 38:8993 CrossRefGoogle Scholar
  20. 20.
    Hiratani K, Uzawa H, Kasuga K, Kambayashi H (1997) J Am Chem Soc 119:12677 CrossRefGoogle Scholar
  21. 21.
    Inokuma S, Kobayashi A, Katoh R, Yasuda T, Nishimura J (1995) Heterocycles 40:401 Google Scholar
  22. 22.
    Inokuma S, Funaki T, Tanakajima M, Isawa K, Nishimura J (2001) Heterocycles 55:1635 CrossRefGoogle Scholar
  23. 23.
    Inokuma S, Kimura K, Nishimura J (2001) J Inclu Phenom Macro Chem 39:30 Google Scholar
  24. 24.
    Inokuma S, Kimura K, Nishimura J (1998) Chem Lett, p 287 Google Scholar
  25. 25.
    Siebert JW, Hundt GR, Sargent AL, Lynch V (2005) Tetrahedron 61:12350 CrossRefGoogle Scholar
  26. 26.
    Siebert JW, Forshee PB, Lynch V (2005) Inorg Chem 44:8602 CrossRefGoogle Scholar
  27. 27.
    Kim H-Y, Lee W-J, Kang H-M, Cho C-G (2007) Org Lett 16:3185 CrossRefGoogle Scholar
  28. 28.
    Inokuma S, Takezawa M, Satoh H, Nakamura Y, Sasaki T, Nisimura J (1998) J Org Chem 63:5791 CrossRefGoogle Scholar
  29. 29.
    Inokuma S, Sakaizawa T, Funaki T, Yonekura T, Satoh H, Kondo S, Nakamura Y, Nishimura J (2003) Tetrahedron 59:8183 CrossRefGoogle Scholar
  30. 30.
    Xu J, Lai Y-H (2002) Org Lett 4:3211 CrossRefGoogle Scholar
  31. 31.
    Xu J, Lai Y-H (2002) Tetrahedron Lett 43:9199 CrossRefGoogle Scholar
  32. 32.
    Xu J, Lai Y-H, Wang W (2003) Org Lett 5:2781 CrossRefGoogle Scholar
  33. 33.
    Mertens IJA, Wegh R, Jenneskens LW, Vliestra EJ, van der K-van Hoof A, Zwikker JW, Cleiji TJ, Wilberth WJJ, Veldman N, Spek AL (1998) J Chem Soc Perkin Trans 2:725 Google Scholar
  34. 34.
    Houjou H, Ogiwara T, Nagawa Y, Hiratani K (2001) J Inclu Phenom Macro Chem 39:347 CrossRefGoogle Scholar
  35. 35.
    Tokuhisa H, Nagawa Y, Uzawa H, Hiratani K (1999) Tetrahedron Lett 40:8007 CrossRefGoogle Scholar
  36. 36.
    Nagawa Y, Fukazawa N, Suga J, Horn M, Tokuhisa H, Hiratani K, Watanabe K (2000) Tetrahedron Lett 41:9261 CrossRefGoogle Scholar
  37. 37.
    Hiratani K, Sakamoto N, Kameta N, Karikomi M, Nagawa Y (2004) Chem Commun, p 1474 Google Scholar
  38. 38.
    Hiratani K, Nagawa Y, Kanasato M (2005) Japan Kokai Tokkyo Koho, p 9 (CODEN:JKXXAF JP 2005075773 A 20050324) Google Scholar
  39. 39.
    Nagawa Y, Hiratani K, Koyama E, Kanesato M (2005) Japan Kokai Tokkyo Koho, p 12 (CODEN:JKXXAF JP 2005022991 A 20050127) Google Scholar
  40. 40.
    Naher S, Hiratani K, Ito S (2006) J Inclu Phenom Macro Chem 55:151 CrossRefGoogle Scholar
  41. 41.
    Lukyanenko NG, Kirichenko TI, Lyapunov AY, Kulygina CY, Lyapunov AY, Simonov YA, Fonari MS, Botoshansky MM (2004) Tetrahedron Lett 45:2927 CrossRefGoogle Scholar
  42. 42.
    Desvergne J-P, Perez-Inestrosa HE, Bouas-Lauarent H, Jonusauskas G, Oberle J, Rulliere C (2001) In: Valeur B, Brochon J-C (eds) Springer Series on Fluorescence 1 (New Trends in Fluorescence Spectroscopy). Springer 157 Google Scholar
  43. 43.
    Marsa P, Guinand G, Hinschberger J, Desvergne J-P, Bouas-Lauarent H (2004) Aust J Chem 57:1085 CrossRefGoogle Scholar
  44. 44.
    Inouye M, Fujimoto K, Furusyo M, Nakazumi H (1999) J Am Chem Soc 121:1452 CrossRefGoogle Scholar
  45. 45.
    Abe H, Mawatari Y, Teraoka H, Fujimoto K, Inouye M (2004) J Org Chem 69:495 CrossRefGoogle Scholar
  46. 46.
    Funaki T, Inokuma S, Ide H, Yonekura T, Nakamura Y, Nishimura J (2004) Tetrahedron Lett 45:2393 CrossRefGoogle Scholar
  47. 47.
    Inokuma S, Ide H, Yonekura T, Funaki T, Kondo S, Shiobara S, Yoshihara T, Tobita S, Nishimura J (2005) J Org Chem 70:1698 CrossRefGoogle Scholar
  48. 48.
    Inokuma S, Yatsuzuka T, Ohtsuki S, Hino S, Nishimura J (2007) Tetrahedron 63:5088 CrossRefGoogle Scholar
  49. 49.
    Kumar S, Hundal M, Maninder S, Hundal G, Singh P, Bhalla V, Singh H (1998) J Chem Soc Perkin Trans 2:925 Google Scholar
  50. 50.
    Baylies CJ, Harding LP, Jeffery JC, Riis-Johannessen T, Rice CR (2004) Angew Chem Int Ed 43:4515 CrossRefGoogle Scholar
  51. 51.
    Bokolinis G, Riis-Johannessen T, Harding LP, Jeffery JC, McLay N, Rice CR (2006) Chem Commun, p 1980 Google Scholar
  52. 52.
    Inokuma S, Kurakami M, Otsuki S, Shirakawa T, Kondo S, Nakamura Y, Nishimura J (2006) Tetrahedron 62:10005 CrossRefGoogle Scholar
  53. 53.
    Cruz C, Delgado R, Drew MGB, Félix V (2007) J Org Chem 72:4023 CrossRefGoogle Scholar
  54. 54.
    Perez-Inestrosa E, Desvergne J-P, Bouas-Laurent H, Rayez J-C, Rayez M-T, Cotrait M, Marsau P (2002) Eur J Org Chem 331 Google Scholar
  55. 55.
    Allwood BL, Spencer N, Shahriari-Zavareh H, Stoddard JF, Williams DJ (1987) J Chem Soc Chem Commun, p 1061 Google Scholar
  56. 56.
    Ashton PR, Slawin AMZ, Spencer N, Stoddard JF, David DJ (1987) J Chem Soc Chem Commun, p 1066 Google Scholar
  57. 57.
    Chas M, Blanco V, Peinador C, Quintela JM (2007) Org Lett 9:675 CrossRefGoogle Scholar
  58. 58.
    Chas M, Pia E, Toba R, Peinador C, Quintela JM (2006) Inorg Chem 45:6117 CrossRefGoogle Scholar
  59. 59.
    Halterman RL, David E, Pan X, Ha DB, Frow M, Haessig K (2006) Org Lett 8:2119 CrossRefGoogle Scholar
  60. 60.
    Nikitin K, Fizmaurice D (2005) J Am Chem Soc 127:8067 CrossRefGoogle Scholar
  61. 61.
    Orita A, Okano J, Tawa Y, Jiang L, Otera J (2004) Angew Chem Int Ed 43:3724 CrossRefGoogle Scholar
  62. 62.
    Feng D-J, Wang X-Z, Jiang X-K, Li Z-T (2004) Tetrahedron 60:6137 CrossRefGoogle Scholar
  63. 63.
    Jiang L, Okano J, Orita A, Otera J (2004) Angew Chem Int Ed 43:2121 CrossRefGoogle Scholar
  64. 64.
    Vibnon SA, Wong J, Tseng H-R, Stoddard JF (2004) Org Lett 6:1095 CrossRefGoogle Scholar
  65. 65.
    Long B, Nikitin K, Fizmaurice D (2003) J Am Chem Soc 125:15490 CrossRefGoogle Scholar
  66. 66.
    Huang F, Jones JW, Slebodnick C, Gibson HW (2003) J Am Chem Soc 125:14458 CrossRefGoogle Scholar
  67. 67.
    Benniston AC, Davies M, Harriman A, Sams C (2003) J Phys Chem A 107:4669 CrossRefGoogle Scholar
  68. 68.
    Nikitin, K Long B, Fizmaurice D (2003) Chem Commun, p 282 Google Scholar
  69. 69.
    Amirsakis DG, Garcia-Garibay MA, Rowan SJ, Stoddart JF, White AJP, Williams DJ (2001) Angew Chem Int Ed 40:4256 CrossRefGoogle Scholar
  70. 70.
    Ashton PR, Baldoni V, Balzani V, Credi A, Hoffmann HDA, Martínez-Díaz M-V, Raymo FM, Stoddart JF, Venturi M (2001) Chem Eur J 7:3482 CrossRefGoogle Scholar
  71. 71.
    Ashton PR, Brown CL, Cao J, Lee J-Y, Simon SP, Raymo FM, Stoddard JF, White AJP, Williams DJ (2001) Eur J Org Chem 2001:957 CrossRefGoogle Scholar
  72. 72.
    Ashton PR, Becher J, Fyfe MCT, Nielsen MB, Stoddard JF, White AJP, Williams DJ (2001) Tetrahedron 57:947 CrossRefGoogle Scholar
  73. 73.
    D'Acerno C, Doddi G, Ercolani G, Mencarelli P (2000) Chem Eur J 6:3540 CrossRefGoogle Scholar
  74. 74.
    Wong EW, Collier CP, Behloradsky M, Raymo FM, Stoddard JF, Heath JR (2000) J Am Chem Soc 122:5831 CrossRefGoogle Scholar
  75. 75.
    Balzani V, Credi A, Langford S, Raymo FM, Stoddard JF, Venturi M (2000) J Am Chem Soc 122:3542 CrossRefGoogle Scholar
  76. 76.
    Mezei G, Kampf JW, Pecoraro VL (2007) New J Chem 31:439 CrossRefGoogle Scholar
  77. 77.
    Chas M, Blanco V, Peinador C, Quintela JM (2007) Org Lett 9:675 CrossRefGoogle Scholar
  78. 78.
    Mendes PM, Lu W, Tseng H-R, Shinder S, Iijima T, Miyaji M, Knobler CM, Stoddard JF (2006) J Phys Chem B 110:3845 CrossRefGoogle Scholar
  79. 79.
    Gunter MJ, Merican Z (2005) Supramol Chem 17:521 CrossRefGoogle Scholar
  80. 80.
    Flood AH, Peters AJ, Scott SA, David W, Tseng H-R, Kang S, James JR, Stoddard JF (2004) Chem Eur J 10:6558 CrossRefGoogle Scholar
  81. 81.
    Ashton PR, Baldoni V, Balzani V, Credi A, Hoffmann HDA, Martinez-Diaz M-V, Raymo FM, Stoddard JF (2001) Chem Eur J 7:3482 CrossRefGoogle Scholar
  82. 82.
    Cabezon B, Cao J, Raymo FM, Stoddard JF, White AJP (2000) Chem Eur J 6:2262 CrossRefGoogle Scholar
  83. 83.
    Cabezon B, Cao J, Raymo FM, Stoddard JF, White AJP, Williams DJ (2000) Angew Chem Int Ed 39:148 CrossRefGoogle Scholar
  84. 84.
    Zhang Q, Hamilton DG, Feeder N, Simon SJ, Goodman JM, Sanders JKM (1999) New J Chem 23:897 CrossRefGoogle Scholar
  85. 85.
    Amabilino DB, Ashton PR, Balzani V, Boyd SE, Credi A, Lee JY, Menzer S, Stoddard JF, Venturi M, Williams DJ (1998) J Am Chem Soc 120:4295 CrossRefGoogle Scholar
  86. 86.
    Flood AH, Peters AJ, Vignon SA, Steuerman DW, Tseng H-R, Kang S, Heath JR, Stoddard JF (2004) Chem Eur J 10:6558 CrossRefGoogle Scholar
  87. 87.
    Ashton PR, Boyd SE, Bribdle A, Langford SJ, Menzer S, Perez-Garcia L, Preece JA, Raymoisco M, Spencer N, Stoddard JF, White AJP, William DJ (1999) New J Chem 23:587 CrossRefGoogle Scholar
  88. 88.
    Ashton PR, Ballardini R, Balzani V, Constable EC, Credi A, Kocian O, Langford SJ, Preece JA, Prodi L, Schofield ER, Spencer N, Stoddard JF, Wenger S (1998) Chem Eur J 4:2413 CrossRefGoogle Scholar
  89. 89.
    Bryce MR, Cooke G, Florence MA, John P, Perepichka DF, Dmitrili F, Polwart N, Rotello VM, Stoddard JF (2003) J Mater Chem 13:2111 CrossRefGoogle Scholar
  90. 90.
    Ashton PR, Balzani V, Becher J, Credi A, Fyfe MCT, Mattersteig G, Menzer S, Nielsen MB, Raymo FM, Stoddard JF, Venturi M, Williams DJ (1999) J Am Chem Soc 121:3951 CrossRefGoogle Scholar
  91. 91.
    Vignon SA, Jarrosson T, Iijima T, Tseng H-R, Sanders JKM, Stoddard JF (2004) J Am Chem Soc 126:9884 CrossRefGoogle Scholar
  92. 92.
    Iijima T, Sanders JKM, Marchioni F, Venturi M, Apostoli E, Balzani V, Stoddard JF (2004) Chem Eur J 10:6375 CrossRefGoogle Scholar
  93. 93.
    Kaiser G, Jarrosson T, Otto S, Ng Y-F, Bond AD, Sanders JKM (2004) Angew Chem Int Ed 43:1959 CrossRefGoogle Scholar
  94. 94.
    Nakamura Y, Minami S, Iizuka K, Nishimura J (2003) Angew Chem Int Ed 42:3158 CrossRefGoogle Scholar
  95. 95.
    Gunter MJ, Bampos N, Johnstone KD, Leremy KM (2001) New J Chem 25:166 CrossRefGoogle Scholar
  96. 96.
    Hamilton DG, Montalti M, Prodi L, Fontani M, Zanello P, Sanders JKM (2000) Chem Eur J 6:608 CrossRefGoogle Scholar
  97. 97.
    Hansen JM, Feeder N, Hamilton DG, Gunter MJ, Becher J, Sanders JKM (2000) Org Lett 2:449 CrossRefGoogle Scholar
  98. 98.
    Hamilton DG, Davies JE, Prodi L, Sanders JMK (1998) Chem Eur J 4:608 CrossRefGoogle Scholar
  99. 99.
    Tseng H-R, Vibnon SA, Celestre PC, Stoddard JF, White AJP, Williams DJ (2003) Chem Eur J 9:543 CrossRefGoogle Scholar
  100. 100.
    Raymo FM, Houk KN, Stoddard JF (1998) J Org Chem 63:6523 CrossRefGoogle Scholar
  101. 101.
    Amabilino DB, Ashton PR, Stoddard JF, White AJP, Williams DJ (1998) Chem Eur J 4:460 CrossRefGoogle Scholar
  102. 102.
    Rogez G, Ferrer RB, Credi A, Ballardini R, Gandolfi MT, Balzani V, Liu Y, Brain H, Stoddard JF (2007) J Am Chem Soc 129:4633 CrossRefGoogle Scholar
  103. 103.
    Asakawa M, Ashton PR, Ballardini R, Balzani V, Belohradsky M, Gandolfi MT, Kocian O, Prodi L, Raymo FM, Stoddard JF, Venturi M (1997) J Am Chem Soc 119:302 CrossRefGoogle Scholar
  104. 104.
    Weck M, Mohr B, Sauvage JP, Grubbs RH (1999) J Org Chem 64:5463 CrossRefGoogle Scholar
  105. 105.
    Hiratani K, Suga J, Nagawa Y, Houjou H, Tokuhisa H, Numata M, Watanabe K (2002) Tetrahedron Lett 43:5747 CrossRefGoogle Scholar
  106. 106.
    Nagawa Y, Hiratani K, Koyama E (2004) Japan Kokai Tokkyo Koho, p 7 (CODEN:JKXXAF JP 2004018402 A 20040122) Google Scholar
  107. 107.
    Kameta N, Hirtani K, Nagawa Y (2004) Chem Commun, p 466 Google Scholar
  108. 108.
    Hiratani K, Kaneyama M, Nagawa Y, Koyama E, Kanesato M (2004) J Am Chem Soc 126:13568 CrossRefGoogle Scholar
  109. 109.
    Nagawa Y, Suga J, Hiratani K, Koyama E, Kanesato M (2005) Chem Commun, p 749 Google Scholar
  110. 110.
    Hirose K, Nishihara K, Harada N, Nakamura Y, Masuda D, Araki M, Tobe Y (2007) Org Lett 16:2969 CrossRefGoogle Scholar
  111. 111.
    Hogan JC, Gandour RD (1992) J Org Chem 57:55 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2008

Authors and Affiliations

  1. 1.Department of Chemistry and Chemical BiologyGraduate School of Engineering, Gunma UniversityGunmaJapan

Personalised recommendations