Skip to main content
SpringerLink
Log in

Syntheses and Properties of Crownophanes

  • Chapter
  • First Online:
Heterocyclic Supramolecules I

Part of the book series: Topics in Heterocyclic Chemistry ((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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Pedersen CJ (1967) J Am Chem Soc 89:7017

    Article  CAS  Google Scholar 

  2. Sutherland IO (1990) In: Gokel GW (ed) Advances in Supermolecular Chemistry, Chap 1. JAI Press, Greenwich, p 65

    Google Scholar 

  3. An H-Y, Bradshaw JS, Izatt RM, Yan Z (1994) Chem Rev 94:939

    Article  CAS  Google Scholar 

  4. Gokel GW (1992) Chem Soc Rev 39:3

    Google Scholar 

  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. Inokuma S, Sakai S, Nishimura J (1994) Top Curr Chem 172:87

    Article  CAS  Google Scholar 

  7. Inokuma S, Yamamoto T, Nishimura (1990) Tetrahedron Lett 31:97

    Article  CAS  Google Scholar 

  8. Inokuma S, Sakai S, Yamamoto T, Nishimura J (1994) J Membr Sci 97:175

    Article  CAS  Google Scholar 

  9. Inokuma S, Gao S-R, Nishimura J (1995) Chem Lett, p 689

    Google Scholar 

  10. Inokuma S, Katoh R, Yamamoto T, Nishimura J (1991) Chem Lett, p 1751

    Google Scholar 

  11. Inokuma S, Saka S, Katoh R, Yasuda T, Nishimura J (1993) Nippon Kagaku Kaishi, p 1148

    Google Scholar 

  12. Inokuma S, Sakai S, Katoh R, Nishimura J (1994) Bull Chem Soc Jpn 67:1462

    Article  CAS  Google Scholar 

  13. Inokuma S, Yasuda T, Araki S, Sakai S, Nishimura J (1994) Chem Lett, p 201

    Google Scholar 

  14. Inokuma S, Kimura K, Funaki T, Nishimura J (2001) Heterocycles 55:447

    CAS  Google Scholar 

  15. Inokuma S, Funaki T, Kondo S, Hara D, Nishimura J (2004) Heterocycles 63:333

    CAS  Google Scholar 

  16. Mateo C, Pérez-Melero C, Pelaéz R, Medardé M (2005) Tetrahedron Lett 46:7055

    Article  CAS  Google Scholar 

  17. Pigge FC, Ghasedi F, Rath NP (2002) J Org Chem 67:4547

    Article  CAS  Google Scholar 

  18. Pigge FC, Ghasedi F, Schitt AV, Dighe MK, Rath NP (2005) Tetrahedron 61:5363

    Article  CAS  Google Scholar 

  19. Hiratani K, Uzawa H, Kasuga K, Kambayashi H (1997) Tetrahedron Lett 38:8993

    Article  CAS  Google Scholar 

  20. Hiratani K, Uzawa H, Kasuga K, Kambayashi H (1997) J Am Chem Soc 119:12677

    Article  CAS  Google Scholar 

  21. Inokuma S, Kobayashi A, Katoh R, Yasuda T, Nishimura J (1995) Heterocycles 40:401

    CAS  Google Scholar 

  22. Inokuma S, Funaki T, Tanakajima M, Isawa K, Nishimura J (2001) Heterocycles 55:1635

    Article  CAS  Google Scholar 

  23. Inokuma S, Kimura K, Nishimura J (2001) J Inclu Phenom Macro Chem 39:30

    Google Scholar 

  24. Inokuma S, Kimura K, Nishimura J (1998) Chem Lett, p 287

    Google Scholar 

  25. Siebert JW, Hundt GR, Sargent AL, Lynch V (2005) Tetrahedron 61:12350

    Article  CAS  Google Scholar 

  26. Siebert JW, Forshee PB, Lynch V (2005) Inorg Chem 44:8602

    Article  CAS  Google Scholar 

  27. Kim H-Y, Lee W-J, Kang H-M, Cho C-G (2007) Org Lett 16:3185

    Article  CAS  Google Scholar 

  28. Inokuma S, Takezawa M, Satoh H, Nakamura Y, Sasaki T, Nisimura J (1998) J Org Chem 63:5791

    Article  CAS  Google Scholar 

  29. Inokuma S, Sakaizawa T, Funaki T, Yonekura T, Satoh H, Kondo S, Nakamura Y, Nishimura J (2003) Tetrahedron 59:8183

    Article  CAS  Google Scholar 

  30. Xu J, Lai Y-H (2002) Org Lett 4:3211

    Article  CAS  Google Scholar 

  31. Xu J, Lai Y-H (2002) Tetrahedron Lett 43:9199

    Article  CAS  Google Scholar 

  32. Xu J, Lai Y-H, Wang W (2003) Org Lett 5:2781

    Article  CAS  Google Scholar 

  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. Houjou H, Ogiwara T, Nagawa Y, Hiratani K (2001) J Inclu Phenom Macro Chem 39:347

    Article  Google Scholar 

  35. Tokuhisa H, Nagawa Y, Uzawa H, Hiratani K (1999) Tetrahedron Lett 40:8007

    Article  CAS  Google Scholar 

  36. Nagawa Y, Fukazawa N, Suga J, Horn M, Tokuhisa H, Hiratani K, Watanabe K (2000) Tetrahedron Lett 41:9261

    Article  CAS  Google Scholar 

  37. Hiratani K, Sakamoto N, Kameta N, Karikomi M, Nagawa Y (2004) Chem Commun, p 1474

    Google Scholar 

  38. Hiratani K, Nagawa Y, Kanasato M (2005) Japan Kokai Tokkyo Koho, p 9 (CODEN:JKXXAF JP 2005075773 A 20050324)

    Google Scholar 

  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. Naher S, Hiratani K, Ito S (2006) J Inclu Phenom Macro Chem 55:151

    Article  CAS  Google Scholar 

  41. Lukyanenko NG, Kirichenko TI, Lyapunov AY, Kulygina CY, Lyapunov AY, Simonov YA, Fonari MS, Botoshansky MM (2004) Tetrahedron Lett 45:2927

    Article  CAS  Google Scholar 

  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. Marsa P, Guinand G, Hinschberger J, Desvergne J-P, Bouas-Lauarent H (2004) Aust J Chem 57:1085

    Article  Google Scholar 

  44. Inouye M, Fujimoto K, Furusyo M, Nakazumi H (1999) J Am Chem Soc 121:1452

    Article  CAS  Google Scholar 

  45. Abe H, Mawatari Y, Teraoka H, Fujimoto K, Inouye M (2004) J Org Chem 69:495

    Article  CAS  Google Scholar 

  46. Funaki T, Inokuma S, Ide H, Yonekura T, Nakamura Y, Nishimura J (2004) Tetrahedron Lett 45:2393

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  48. Inokuma S, Yatsuzuka T, Ohtsuki S, Hino S, Nishimura J (2007) Tetrahedron 63:5088

    Article  CAS  Google Scholar 

  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. Baylies CJ, Harding LP, Jeffery JC, Riis-Johannessen T, Rice CR (2004) Angew Chem Int Ed 43:4515

    Article  CAS  Google Scholar 

  51. Bokolinis G, Riis-Johannessen T, Harding LP, Jeffery JC, McLay N, Rice CR (2006) Chem Commun, p 1980

    Google Scholar 

  52. Inokuma S, Kurakami M, Otsuki S, Shirakawa T, Kondo S, Nakamura Y, Nishimura J (2006) Tetrahedron 62:10005

    Article  CAS  Google Scholar 

  53. Cruz C, Delgado R, Drew MGB, Félix V (2007) J Org Chem 72:4023

    Article  CAS  Google Scholar 

  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. Allwood BL, Spencer N, Shahriari-Zavareh H, Stoddard JF, Williams DJ (1987) J Chem Soc Chem Commun, p 1061

    Google Scholar 

  56. Ashton PR, Slawin AMZ, Spencer N, Stoddard JF, David DJ (1987) J Chem Soc Chem Commun, p 1066

    Google Scholar 

  57. Chas M, Blanco V, Peinador C, Quintela JM (2007) Org Lett 9:675

    Article  CAS  Google Scholar 

  58. Chas M, Pia E, Toba R, Peinador C, Quintela JM (2006) Inorg Chem 45:6117

    Article  CAS  Google Scholar 

  59. Halterman RL, David E, Pan X, Ha DB, Frow M, Haessig K (2006) Org Lett 8:2119

    Article  CAS  Google Scholar 

  60. Nikitin K, Fizmaurice D (2005) J Am Chem Soc 127:8067

    Article  CAS  Google Scholar 

  61. Orita A, Okano J, Tawa Y, Jiang L, Otera J (2004) Angew Chem Int Ed 43:3724

    Article  CAS  Google Scholar 

  62. Feng D-J, Wang X-Z, Jiang X-K, Li Z-T (2004) Tetrahedron 60:6137

    Article  CAS  Google Scholar 

  63. Jiang L, Okano J, Orita A, Otera J (2004) Angew Chem Int Ed 43:2121

    Article  CAS  Google Scholar 

  64. Vibnon SA, Wong J, Tseng H-R, Stoddard JF (2004) Org Lett 6:1095

    Article  CAS  Google Scholar 

  65. Long B, Nikitin K, Fizmaurice D (2003) J Am Chem Soc 125:15490

    Article  CAS  Google Scholar 

  66. Huang F, Jones JW, Slebodnick C, Gibson HW (2003) J Am Chem Soc 125:14458

    Article  CAS  Google Scholar 

  67. Benniston AC, Davies M, Harriman A, Sams C (2003) J Phys Chem A 107:4669

    Article  CAS  Google Scholar 

  68. Nikitin, K Long B, Fizmaurice D (2003) Chem Commun, p 282

    Google Scholar 

  69. Amirsakis DG, Garcia-Garibay MA, Rowan SJ, Stoddart JF, White AJP, Williams DJ (2001) Angew Chem Int Ed 40:4256

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  Google Scholar 

  72. Ashton PR, Becher J, Fyfe MCT, Nielsen MB, Stoddard JF, White AJP, Williams DJ (2001) Tetrahedron 57:947

    Article  CAS  Google Scholar 

  73. D'Acerno C, Doddi G, Ercolani G, Mencarelli P (2000) Chem Eur J 6:3540

    Article  Google Scholar 

  74. Wong EW, Collier CP, Behloradsky M, Raymo FM, Stoddard JF, Heath JR (2000) J Am Chem Soc 122:5831

    Article  CAS  Google Scholar 

  75. Balzani V, Credi A, Langford S, Raymo FM, Stoddard JF, Venturi M (2000) J Am Chem Soc 122:3542

    Article  CAS  Google Scholar 

  76. Mezei G, Kampf JW, Pecoraro VL (2007) New J Chem 31:439

    Article  CAS  Google Scholar 

  77. Chas M, Blanco V, Peinador C, Quintela JM (2007) Org Lett 9:675

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  79. Gunter MJ, Merican Z (2005) Supramol Chem 17:521

    Article  CAS  Google Scholar 

  80. Flood AH, Peters AJ, Scott SA, David W, Tseng H-R, Kang S, James JR, Stoddard JF (2004) Chem Eur J 10:6558

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  82. Cabezon B, Cao J, Raymo FM, Stoddard JF, White AJP (2000) Chem Eur J 6:2262

    Article  CAS  Google Scholar 

  83. Cabezon B, Cao J, Raymo FM, Stoddard JF, White AJP, Williams DJ (2000) Angew Chem Int Ed 39:148

    Article  CAS  Google Scholar 

  84. Zhang Q, Hamilton DG, Feeder N, Simon SJ, Goodman JM, Sanders JKM (1999) New J Chem 23:897

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  86. Flood AH, Peters AJ, Vignon SA, Steuerman DW, Tseng H-R, Kang S, Heath JR, Stoddard JF (2004) Chem Eur J 10:6558

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  91. Vignon SA, Jarrosson T, Iijima T, Tseng H-R, Sanders JKM, Stoddard JF (2004) J Am Chem Soc 126:9884

    Article  CAS  Google Scholar 

  92. Iijima T, Sanders JKM, Marchioni F, Venturi M, Apostoli E, Balzani V, Stoddard JF (2004) Chem Eur J 10:6375

    Article  CAS  Google Scholar 

  93. Kaiser G, Jarrosson T, Otto S, Ng Y-F, Bond AD, Sanders JKM (2004) Angew Chem Int Ed 43:1959

    Article  CAS  Google Scholar 

  94. Nakamura Y, Minami S, Iizuka K, Nishimura J (2003) Angew Chem Int Ed 42:3158

    Article  CAS  Google Scholar 

  95. Gunter MJ, Bampos N, Johnstone KD, Leremy KM (2001) New J Chem 25:166

    Article  CAS  Google Scholar 

  96. Hamilton DG, Montalti M, Prodi L, Fontani M, Zanello P, Sanders JKM (2000) Chem Eur J 6:608

    Article  CAS  Google Scholar 

  97. Hansen JM, Feeder N, Hamilton DG, Gunter MJ, Becher J, Sanders JKM (2000) Org Lett 2:449

    Article  CAS  Google Scholar 

  98. Hamilton DG, Davies JE, Prodi L, Sanders JMK (1998) Chem Eur J 4:608

    Article  CAS  Google Scholar 

  99. Tseng H-R, Vibnon SA, Celestre PC, Stoddard JF, White AJP, Williams DJ (2003) Chem Eur J 9:543

    Article  CAS  Google Scholar 

  100. Raymo FM, Houk KN, Stoddard JF (1998) J Org Chem 63:6523

    Article  CAS  Google Scholar 

  101. Amabilino DB, Ashton PR, Stoddard JF, White AJP, Williams DJ (1998) Chem Eur J 4:460

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  104. Weck M, Mohr B, Sauvage JP, Grubbs RH (1999) J Org Chem 64:5463

    Article  CAS  Google Scholar 

  105. Hiratani K, Suga J, Nagawa Y, Houjou H, Tokuhisa H, Numata M, Watanabe K (2002) Tetrahedron Lett 43:5747

    Article  CAS  Google Scholar 

  106. Nagawa Y, Hiratani K, Koyama E (2004) Japan Kokai Tokkyo Koho, p 7 (CODEN:JKXXAF JP 2004018402 A 20040122)

    Google Scholar 

  107. Kameta N, Hirtani K, Nagawa Y (2004) Chem Commun, p 466

    Google Scholar 

  108. Hiratani K, Kaneyama M, Nagawa Y, Koyama E, Kanesato M (2004) J Am Chem Soc 126:13568

    Article  CAS  Google Scholar 

  109. Nagawa Y, Suga J, Hiratani K, Koyama E, Kanesato M (2005) Chem Commun, p 749

    Google Scholar 

  110. Hirose K, Nishihara K, Harada N, Nakamura Y, Masuda D, Araki M, Tobe Y (2007) Org Lett 16:2969

    Article  CAS  Google Scholar 

  111. Hogan JC, Gandour RD (1992) J Org Chem 57:55

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry and Chemical Biology, Graduate School of Engineering, Gunma University, Tenjin-cho, Kiryu 376-8515, Gunma, Japan

    S. Inokuma, M. Ito & J. Nishimura

Authors
  1. S. Inokuma
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Ito
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. J. Nishimura
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to J. Nishimura .

Editor information

Kiyoshi Matsumoto

Rights and permissions

Reprints and permissions

Copyright information

© 2008 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Inokuma, S., Ito, M., Nishimura, J. (2008). Syntheses and Properties of Crownophanes. In: Matsumoto, K. (eds) Heterocyclic Supramolecules I. Topics in Heterocyclic Chemistry, vol 17. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2008_116

Download citation

Publish with us

Policies and ethics

Search

Navigation