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Molecular Recognition with Designed Heterocycles and Their Lanthanide Complexes

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Heterocyclic Supramolecules I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 17))

Abstract

Molecular recognition with designed heterocycles and their lanthanide complexes in the solution states was mainly described. Various synthetic receptors for specific binding of cationic and anionic guests were presented, in which several weak interactions were combined to fit the size, shape, geometry, and electronic characteristics of the specific guest species. The cation-ligating heterocycles were successfully organized in the receptor molecules to exhibit high selectivity and efficiency in the cation recognition and sensing. A series of N-protonated and substituted heterocycles had the potentials as anion receptors effective in aqueous media. Furthermore, the designed heterocycle-lanthanide complexes worked as luminescent sensory devices of biologically important anions. The examples presented here clearly indicated that a variety of heterocycles acted as useful building blocks in the receptor architecture. The sophisticated molecular synthesis using potential heterocycles can provide specific recognition at the molecular and supramolecular levels.

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References

  1. Atwood AL, Davies JED, MacNicol DD, Vögtle F (eds) (1996) Comprehensive supramolecular chemistry, vol 1, 2, and 6. Pergamon, New York

    Google Scholar 

  2. Sauvage JP (1990) Acc Chem Res 23:319

    CAS  Google Scholar 

  3. Fujita M, Ogura K (1996) Coord Chem Rev 148:249

    CAS  Google Scholar 

  4. Dutzler R, Campbell EB, MacKinnon R (2003) Science 300:108

    CAS  Google Scholar 

  5. Dutzler R, Campbell EB, Cadene M, Chait BT, MacKinnon R (2002) Nature 415:287

    CAS  Google Scholar 

  6. Clare JP, Ayling AJ, Joos J-B, Sisson AL, Magro G, Pérez-Payán MN, Lambert TN, Shukla R, Smith BD, Davis AP (2005) J Am Chem Soc 127:10739

    CAS  Google Scholar 

  7. Davis JT (2004) Angew Chem Int Ed 43:668

    CAS  Google Scholar 

  8. Boyd PDW, Reed CA (2005) Acc Chem Res 38:235

    CAS  Google Scholar 

  9. Sato H, Tashiro K, Shinmori H, Osuka A, Murata Y, Komatsu K, Aida T (2005) J Am Chem Soc 127:13086

    CAS  Google Scholar 

  10. Prince RB, Barnes SA, Moore JS (2000) J Am Chem Soc 122:2758

    CAS  Google Scholar 

  11. Garric J, Léger J-M, Huc I (2005) Angew Chem Int Ed 44:1954

    CAS  Google Scholar 

  12. Waki M, Abe H, Inouye M (2007) Angew Chem Int Ed 46:3059

    CAS  Google Scholar 

  13. Kumar S, Paul D, Singh H (2005) Adv Heterocycl Chem 89:65

    CAS  Google Scholar 

  14. Morohashi N, Narumi F, Iki N, Hattori T, Miyano S (2006) Chem Rev 106:5291

    CAS  Google Scholar 

  15. Ishibashi K, Tsue H, Tokita S, Matsui K, Takahashi H, Tamura R (2006) Org Lett 8:5991

    CAS  Google Scholar 

  16. Tsukube H, Yamada T, Shinoda S (2000) Ind Eng Chem Res 39:3412

    CAS  Google Scholar 

  17. Tsukube H, Shinoda S, Uenishi J, Hiraoka, Imakoga T, Yonemitsu O (1998) J Org Chem 63:3884

    CAS  Google Scholar 

  18. Tsukube H, Yamada T, Shinoda S (2004) J Alloys Compd 374:40

    CAS  Google Scholar 

  19. Tsukube H (1990) In: Inoue Y, Gokel GW (eds) Cation binding by macrocycles. Marcel Dekker, New York, p 487

    Google Scholar 

  20. Erickson SD, Still WC (1990) Tetrahedron Lett 31:4253

    CAS  Google Scholar 

  21. Dai Z, Xu X, Canary JW (2002) Chem Commun, p 1414

    Google Scholar 

  22. Kataoka Y, Paul D, Miyake H, Shinoda S, Tsukube H (2007) Dalton Trans 2784

    Google Scholar 

  23. Yamada Y, Shinoda S, Sugimoto H, Uenishi J, Tsukube H (2003) Inorg Chem 42:7932

    CAS  Google Scholar 

  24. Tsukube H (1996) Coord Chem Rev 148:1

    CAS  Google Scholar 

  25. Tsukube H, Yamada T, Shinoda S (2001) J Hetrocycl Chem 38:1401

    Article  CAS  Google Scholar 

  26. van Unen D-J, Engbersen KFJ, Reinhoudt DN (2001) J Mol Catal B: Enzym 11:877

    Google Scholar 

  27. Itoh T, Takagi Y, Tsukube H (1997) J Mol Catal B: Enzym 3:259

    CAS  Google Scholar 

  28. Odell B, Earlam G (1985) J Chem Soc Chem Commun, p 359

    Google Scholar 

  29. Julian RR, Beauchamp JL (2001) Int J Mass Spectrom 613:210–211

    Google Scholar 

  30. Paul D, Suzumura A, Sugimoto H, Teraoka J, Shinoda S, Tsukube H (2003) J Am Chem Soc 125:11478

    CAS  Google Scholar 

  31. Hamuro Y, Calama MC, Park HS, Hamilton AD (1997) Angew Chem Int Ed Engl 36:2680

    CAS  Google Scholar 

  32. Oshima T, Goto M, Furusaki S (2002) Biomacromolecules 3:438

    CAS  Google Scholar 

  33. Paul D, Miyake H, Shinoda S, Tsukube H (2006) Chem Eur J 12:1328

    CAS  Google Scholar 

  34. Shinoda S, Ohashi M, Tsukube H (2007) Chem Eur J 13:81

    Google Scholar 

  35. Tsukube H, Suzuki Y, Paul D, Kataoka Y, Shinoda S (2007) Chem Commun, p 2533

    Google Scholar 

  36. Park CH, Simmons HE (1968) J Am Chem Soc 90:2431

    CAS  Google Scholar 

  37. Schmidtchen FP, Müller GJ (1980) Chem Ber 113:864

    CAS  Google Scholar 

  38. Schmidtchen FP, Müller GJ (1984) Chem Commun, p 1115

    Google Scholar 

  39. Dietrich B, Guilhem J, Lehn J-M, Pascard C, Sonveaux E (1984) Helv Chim Acta 67:91

    CAS  Google Scholar 

  40. Hosseini H, Lehn J-M (1986) Helv Chim Acta 69:587

    CAS  Google Scholar 

  41. Bianch A, Bowman-James K, García-España (eds) (1997) Supramolecular chemistry of anions. Wiley-VCH, New York

    Google Scholar 

  42. Beer PD, Gale PA (2001) Angew Chem Int Ed 40:486

    CAS  Google Scholar 

  43. Sessler JL, Gale PA, Cho W-S (2006) Anion Receptor Chemistry. RSC Publishing, Cambridge

    Google Scholar 

  44. Bryantsev VS, Hay BP (2005) J Am Chem Soc 127:8282

    CAS  Google Scholar 

  45. Berryman OB, Bryantsev VS, Stay DP, Johnson DW, Hay BP (2006) J Am Chem Soc 129:48

    Google Scholar 

  46. Choi K, Hamilton AD (2003) Coord Chem Rev 240:101

    CAS  Google Scholar 

  47. García-España E, Díaz P, Llinares JM, Bianchi A (2006) Coord Chem Rev 250:2952

    Google Scholar 

  48. Wichmann K, Antonioli B, Söhnel T, Wenzel M, Gloe K, Price JR, Lindoy LF, Blake AJ, Schröder M (2006) Coord Chem Rev 250:2987

    CAS  Google Scholar 

  49. Tabushi I, Kumura Y, Yamamura K (1978) J Am Chem Soc 100:1304

    CAS  Google Scholar 

  50. Tabushi I, Kumura Y, Yamamura K (1981) J Am Chem Soc 103:6486

    CAS  Google Scholar 

  51. Cramer RE, Fermin V, Kuwabara E, Kirkup R, Selman M, Aoki K, Adeyemo A, Yamazaki H (1991) J Am Chem Soc 113:7033

    CAS  Google Scholar 

  52. Cramer RE, Carrié MJ (1990) Inorg Chem 29:3902

    CAS  Google Scholar 

  53. Cramer RE, Mitchell KA, Hirazumi AY, Smith SL (1994) J Chem Soc Dalton Trans 563

    Google Scholar 

  54. Cramer RE, Smith DW, VanDoorne W (1998) Inorg Chem 37:5895

    CAS  Google Scholar 

  55. Shinoda S, Tadokoro M, Tsukube H, Arakawa R (1998) Chem Commun, p 181

    Google Scholar 

  56. Cabildo P, Sanz D, Claramunt RM, Rourne SA, Alkorta I, Elguero J (1999) Tetrahedron 55:2327

    CAS  Google Scholar 

  57. Alcalde E, Alvarez-Rúa C, García-Granda S, García-Rodriguez E, Mesquida N, Pérez-García L (1999) Chem Commun, p 295

    Google Scholar 

  58. Ramos S, Alcalde E, Doddi G, Mencarelli P, Pérez-García L (2002) J Org Chem 67:8463

    CAS  Google Scholar 

  59. Chellappan K, Singh NJ, Hwang I-C, Lee JW, Kim KS (2005) Angew Chem Int Ed 44:2899

    CAS  Google Scholar 

  60. Sato K, Arai S, Yamagishi T (1999) Tetrahedron Lett 40:5219

    CAS  Google Scholar 

  61. Ihm H, Yun S, Kim HG, Kim JK, Kim KS (2002) Org Lett 4:2897

    CAS  Google Scholar 

  62. Yoon J, Kim SJ, Singh NJ, Kim KS (2006) Chem Soc Rev 35:355

    CAS  Google Scholar 

  63. Abouderbala LO, Belcher WJ, Boutelle MG, Cragg PJ, Dhaliwal J, Fabre M, Steed JW, Turner DR, Wallace KJ (2002) Chem Commun, p 358

    Google Scholar 

  64. Wallace KJ, Belcher WJ, Turner DR, Syed KF, Steed JW (2003) J Am Chem Soc 125:9699

    CAS  Google Scholar 

  65. Ilioudis CA, Tocher DA, Steed JW (2004) J Am Chem Soc 126:12395

    CAS  Google Scholar 

  66. Gale PA (2000) Coord Chem Rev 199:181

    CAS  Google Scholar 

  67. Gale PA (2001) Coord Chem Rev 213:79

    CAS  Google Scholar 

  68. Gale PA (2003) Coord Chem Rev 240:191

    CAS  Google Scholar 

  69. Gale PA, Quesada R (2006) Coord Chem Rev 250:3219

    CAS  Google Scholar 

  70. Kang SO, Hossain MA, Bowman-James K (2006) Coord Chem Rev 250:3038

    CAS  Google Scholar 

  71. Kang SO, Begun RA, Bowman-James K (2006) Angew Chem Int Ed 45:7882

    CAS  Google Scholar 

  72. Sessler JL, Cyr MJ, Lynch V, McGhee E, Ibers JA (1990) J Am Chem Soc 112:2810

    CAS  Google Scholar 

  73. Shionoya M, Furuta H, Lynch V, Harriman A, Sessler JL (1992) J Am Chem Soc 114:5714

    CAS  Google Scholar 

  74. Gale PA, Sessler JL, Král V, Lynch V (1996) J Am Chem Soc 118:5140

    CAS  Google Scholar 

  75. Sessler JL, An D, Cho W-S, Lynch V (2003) J Am Chem Soc 125:13646

    CAS  Google Scholar 

  76. Sessler JL, An D, Cho W-S, Lynch V (2003) Angew Chem Int Ed 42:2278

    CAS  Google Scholar 

  77. Sessler JL, An D, Cho W-S, Lynch V, Marquez M (2005) Chem Eur J 11:2001

    CAS  Google Scholar 

  78. Gale PA, Camiolo S, Tizzard GJ, Chapman CP, Light ME, Coles SJ, Hursthouse MB (2001) J Org Chem 66:7849

    CAS  Google Scholar 

  79. Gale PA (2006) Acc Chem Res 39:465

    CAS  Google Scholar 

  80. Chmielewski MJ, Charon M, Jurczak J (2004) Org Lett 6:3501

    CAS  Google Scholar 

  81. Maeda H, Ito Y (2006) Inorg Chem 45:8205

    CAS  Google Scholar 

  82. Maeda H, Kusunose Y (2005) Chem Eur J 11:5661

    CAS  Google Scholar 

  83. Chang K-L, Moon D, Lah MS, Jeong K-S (2005) Angew Chem Int Ed 44:7926

    CAS  Google Scholar 

  84. Katayev EA, Boev NV, Khrustalev VN, Ustynyuk YA, Tananaev IG, Sessler JL (2007) J Org Chem 72:2886

    CAS  Google Scholar 

  85. Martínez-Máñez R, Sancenón F (2003) Chem Rev 103:4419

    Google Scholar 

  86. Suksai C, Tuntulani T (2003) Chem Soc Rev 32:192

    CAS  Google Scholar 

  87. Black CB, Andrioletti B, Try AC, Ruiperez C, Sessler JL (1999) J Am Chem Soc 121:10438

    CAS  Google Scholar 

  88. Nishiyabu R, Anzenbacher P jr (2005) J Am Chem Soc 127:8270

    CAS  Google Scholar 

  89. Evans LS, Gale PA, Light ME, Quesada R (2006) Chem Commun, p 965

    Google Scholar 

  90. Nguyen BT, Anslyn EV (2006) Coord Chem Rev 250:3118

    CAS  Google Scholar 

  91. Metzger A, Anslyn EV (1998) Angew Chem Int Ed 37:649

    CAS  Google Scholar 

  92. Piatek AM, Bomble YJ, Wiskur SL, Anslyn EV (2004) J Am Chem Soc 126:6072

    CAS  Google Scholar 

  93. Wiskur SL, Anslyn EV (2001) J Am Chem Soc 123:10109

    CAS  Google Scholar 

  94. Gale PA, Twyman LJ, Handlin CI, Sessler JL (1999) Chem Commun, p 1851

    Google Scholar 

  95. Atilgan S, Akkaya EU (2004) Tetrahedron Lett 45:9269

    CAS  Google Scholar 

  96. Beer PD, Hayes EJ (2003) Coord Chem Rev 240:167

    CAS  Google Scholar 

  97. Sigel A, Sigel H (eds) (2003) Metal ions in biological systems, vol 40. Marcel Dekker, New York

    Google Scholar 

  98. Parker D (2004) Chem Soc Rev 33:156

    CAS  Google Scholar 

  99. Tsukube H, Shinoda S (2002) Chem Rev 102:2389

    CAS  Google Scholar 

  100. Shinoda S, Miyake H, Tsukube H (2005) Handbook on the physics and chemistry of rare earths 35:273

    Google Scholar 

  101. Di Bari L, Salvadori P (2005) Coord Chem Rev 249:2854

    Google Scholar 

  102. Riehl JP, Muller G (2005) Handbook on the physics and chemistry of rare earths 34:289

    Google Scholar 

  103. Wenzel TJ, Wilcox JD (2003) Chirality 15:256

    CAS  Google Scholar 

  104. Rothchild R, Wyss H (1994) Spectrosc Lett 27:225

    CAS  Google Scholar 

  105. Inamoto A, Ogasawara K, Omata K, Kabuto K, Sasaki Y (2000) Org Lett 2:3543

    CAS  Google Scholar 

  106. Di Bari L, Lelli M, Pintacuda G, Salvadori P (2002) Chirality 14:265

    Google Scholar 

  107. Aime S, Botta M, Parker D, Williams JAG (1995) J Chem Soc Dalton Trans 2259

    Google Scholar 

  108. Aime S, Botta M, Crich SG, Terreno E, Anelli PL, Uggeri F (1999) Chem Eur J 5:1261

    CAS  Google Scholar 

  109. Corsi DM, van Bekkum H, Peters JA (2000) Inorg Chem 39:4802

    CAS  Google Scholar 

  110. Lakowicz JR (1999) Principles of fluorescence spectroscopy, 2nd edn. Springer, Berlin Heidelberg New York

    Google Scholar 

  111. Valeur B (2002) Molecular fluorescence: principles and applications. Wiley-VCH, Weinheim

    Google Scholar 

  112. Douce L, Charbonnière L, Cesario M, Ziessel R (2001) New J Chem 25:1024

    CAS  Google Scholar 

  113. Cho EJ, Moon JW, Ko SW, Lee JY, Kim SK, Yoon J, Nam KC (2003) J Am Chem Soc 125:12376

    CAS  Google Scholar 

  114. Richardson FS (1982) Chem Rev 82:541

    CAS  Google Scholar 

  115. Comby S, Bünzli J-CG (2007) Handbook on the physics and chemistry of rare earths 37:217

    CAS  Google Scholar 

  116. Reuben J (1979) J Chem Soc Chem Commun, p 68

    Google Scholar 

  117. Reuben J (1980) J Am Chem Soc 102:2232

    CAS  Google Scholar 

  118. Bünzli J-CG (1989) In: Bünzli J-CG, Choppin GR (eds) Lanthanide probes in life, chemical and earth sciences. Elsevier, Amsterdam, p 219

    Google Scholar 

  119. Parker D, Dickins RS, Puschmann H, Crossland C, Howard JAK (2002) Chem Rev 102:1977

    CAS  Google Scholar 

  120. Mathis G (1995) Clin Chem 41:1391

    CAS  Google Scholar 

  121. Dickson EFG, Pollack A, Diamandis EP (1995) J Photochem Photobiol B 27:3

    CAS  Google Scholar 

  122. Elbanowski M, Makowska B (1996) J Photochem Photobiol A 99:85

    CAS  Google Scholar 

  123. Faulkner S, Mattews JL (2003) In: Ward MD (ed) Comprehensive coordination chemistry II, vol 9. Elsevier, Amsterdam, p 913

    Google Scholar 

  124. Balzani V, Sabbatini N, Scandola F (1986) Chem Rev 86:319

    CAS  Google Scholar 

  125. Montalti M, Prodi L, Zaccheroni N, Charbonnière L, Douce L, Ziessel R (2001) J Am Chem Soc 123:12694

    CAS  Google Scholar 

  126. Charbonnière LJ, Ziessel R, Montalti M, Prodi L, Zaccheroni N, Boehme C, Wipff G (2002) J Am Chem Soc 124:7779

    Google Scholar 

  127. Yamada T, Shinoda S, Tsukube H (2002) Chem Commun, p 1218

    Google Scholar 

  128. Best MD, Anslyn EV (2003) Chem Eur J 9:51

    CAS  Google Scholar 

  129. Dickins RS, Gunnlaugsson T, Parker D, Peacock RD (1998) Chem Commun, p 1643

    Google Scholar 

  130. Bruce JI, Dickins RS, Govenlock LJ, Gunnlaugsson T, Lopinski S, Lowe MP, Parker D, Peacock RD, Perry JJB, Aime S, Botta M (2000) J Am Chem Soc 122:9674

    CAS  Google Scholar 

  131. Mameri S, Charbonnière LJ, Ziessel RF (2003) Synthesis 17:2713

    Google Scholar 

  132. Charbonnière LJ, Schurhammer R, Mameri S, Wipff G, Ziessel RF (2005) Inorg Chem 44:7151

    Google Scholar 

  133. Ziessel RF, Charbonnière LJ, Mameri S, Camerel F (2005) J Org Chem 70:9835

    CAS  Google Scholar 

  134. Magennis SW, Craig J, Gardner A, Fucassi F, Cragg PJ, Robertson N, Parsons S, Pikramenou Z (2003) Polyhedron 22:745

    CAS  Google Scholar 

  135. Gunnlaugsson T, Harte AJ, Leonard JP, Nieuwenhuyzen M (2002) Chem Commun, p 2134

    Google Scholar 

  136. Leonard JP, dos Santos CMG, Plush SE, McCabe T, Gunnlaugsson T (2007) Chem Commun, p 129

    Google Scholar 

  137. Parker D, Senanayake K, Williams JAG (1997) Chem Commun, p 1777

    Google Scholar 

  138. Parker D, Senanayake K, Williams JAG (1998) J Chem Soc Perkin Trans 2:2129

    Google Scholar 

  139. Yu J, Parker D (2005) Eur J Org Chem 4249

    Google Scholar 

  140. Parker D, Yu J (2005) Chem Commun, p 3141

    Google Scholar 

  141. Terreno E, Botta M, Fedeli F, Mondino B, Milone L, Aime S (2003) Inorg Chem 42:4891

    CAS  Google Scholar 

  142. Dickins RS, Love CS, Puschmann H (2001) Chem Commun, p 2308

    Google Scholar 

  143. Dickins RS, Badari A (2006) Dalton Trans 3088

    Google Scholar 

  144. Yamada T, Shinoda S, Kikawa K, Ichimura A, Teraoka J, Takui T, Tsukube T (2000) Inorg Chem 39:3049

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Graduate School of Science, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, 558-8585, Osaka, Japan

    Samir Mameri, Satoshi Shinoda & Hiroshi Tsukube

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  1. Samir Mameri
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  2. Satoshi Shinoda
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  3. Hiroshi Tsukube
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Correspondence to Hiroshi Tsukube .

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Kiyoshi Matsumoto

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Mameri, S., Shinoda, S., Tsukube, H. (2007). Molecular Recognition with Designed Heterocycles and Their Lanthanide Complexes. In: Matsumoto, K. (eds) Heterocyclic Supramolecules I. Topics in Heterocyclic Chemistry, vol 17. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_092

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