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Dynamic Helical Structures: Detection and Amplification of Chirality

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Supramolecular Chirality

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 265))

Abstract

A unique feature of dynamic helical, chromophoric macromolecules that enables the detection of a small imbalance in chiral guest molecules through a noncovalent bonding interaction with high cooperativity is described. In sharp contrast to host–guest and supramolecular systems based on small synthetic receptor molecules, the chiral information of nonracemic guest molecules transfers with a significant amplification in a helical polymer as an excess of a single-handed helix, resulting in a highly efficient chirality-sensing system. Helical aggregates with controlled helicity based on small molecules and their chiral amplification and use in chirality sensing are also briefly described in this review.

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References

  1. Saenger W (1984) Principles of nucleic acid structure. Springer, Berlin Heidelberg New York

    Google Scholar 

  2. Schulz GE, Schirmer RH (1979) Principles of protein structure. Springer, Berlin Heidelberg New York

    Google Scholar 

  3. Okamoto Y, Nakano T (1994) Chem Rev 94:349

    CAS  Google Scholar 

  4. Green MM, Peterson NC, Sato T, Teramoto A, Cook R, Lifson S (1995) Science 268:1860

    CAS  Google Scholar 

  5. Nakano T, Okamoto Y (2001) Chem Rev 101:4013

    CAS  Google Scholar 

  6. Cornelissen JJLM, Rowan AE, Nolte RJM, Sommerdijk NAJM (2001) Chem Rev 101:4039

    CAS  Google Scholar 

  7. Fujiki M (2001) Macromol Rapid Commun 22:539

    CAS  Google Scholar 

  8. Yashima E, Matsushima T, Okamoto Y (1995) J Am Chem Soc 117:11596

    CAS  Google Scholar 

  9. Yashima E, Matsushima T, Okamoto Y (1997) J Am Chem Soc 119:6345

    CAS  Google Scholar 

  10. Yashima E (2002) Anal Sci 18:3

    CAS  Google Scholar 

  11. Yashima E, Maeda K, Nishimura T (2004) Chem Eur J 10:43

    Google Scholar 

  12. Berova N, Nakanishi K, Woody RW (2000) Circular dichroism: principles and applications, 2nd edn. Wiley, New York

    Google Scholar 

  13. Canary JW, Holmes AE, Liu J (2001) Enantiomer 6:181

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  15. Allenmark S (2003) Chirality 15:409

    CAS  Google Scholar 

  16. Hill DJ, Mio MJ, Prince RB, Hughes TS, Moore JS (2001) Chem Rev 101:3893

    CAS  Google Scholar 

  17. Rowan AE, Nolte RJM (1998) Angew Chem Int Ed 37:63

    CAS  Google Scholar 

  18. Brunsveld L, Folmer BJB, Meijer EW, Sijbesma RP (2001) Chem Rev 101:4071

    CAS  Google Scholar 

  19. Schmuck C (2003) Angew Chem Int Ed 42:2448

    CAS  Google Scholar 

  20. Mateos-Timoneda MA, Crego-Calama M, Reinhoudt DN (2004) Chem Soc Rev 33:363

    CAS  Google Scholar 

  21. Hoeben FJM, Jonkheijm P, Meijer EW, Schenning APHJ (2005) Chem Rev 105:1491

    CAS  Google Scholar 

  22. Zhang J, Albelda T, Liu Y, Canary JW (2005) Chirality 17:404

    CAS  Google Scholar 

  23. Keizer HM, Sijbesma RP (2005) Chem Soc Rev 34:226

    CAS  Google Scholar 

  24. Constable EC (1992) Tetrahedron 48:10013

    CAS  Google Scholar 

  25. Lehn J-M (1995) Supramolecular chemistry. Wiley-VCH, Weinheim, Germany

    Google Scholar 

  26. Piguet C, Bernardinelli G, Hopfgartner G (1997) Chem Rev 97:2005

    CAS  Google Scholar 

  27. Albrecht M (2001) Chem Rev 101:3457

    CAS  Google Scholar 

  28. Tachibana T, Kambara H (1965) J Am Chem Soc 87:3015

    CAS  Google Scholar 

  29. Nakashima N, Asakuma S, Kunitake T (1985) J Am Chem Soc 107:509

    CAS  Google Scholar 

  30. Fuhrhop JH, Helfrich W (1993) Chem Rev 93:1565

    CAS  Google Scholar 

  31. Shimizu T, Masuda M, Minamikawa H (2005) Chem Rev 105:1401

    CAS  Google Scholar 

  32. Terech P, Weiss RG (1997) Chem Rev 97:3133

    CAS  Google Scholar 

  33. Van Bommel KJC, Friggeri A, Shinkai S (2003) Angew Chem Int Ed 42:980

    Google Scholar 

  34. Messmore BW, Sukerkar PA, Stupp SI (2005) J Am Chem Soc 127:7992

    CAS  Google Scholar 

  35. Engelkamp H, Middelbeek S, Nolte RJM (1999) Science 284:785

    CAS  Google Scholar 

  36. Fox JM, Katz TJ, Van Elshocht S, Verbiest T, Kauranen M, Persoons A, Thongpanchang T, Krauss T, Brus L (1999) J Am Chem Soc 121:3453

    CAS  Google Scholar 

  37. Hill JP, Jin W, Kosaka A, Fukushima T, Ichihara H, Shimomura T, Ito K, Hashizume T, Ishii N, Aida T (2004) Science 304:1481

    CAS  Google Scholar 

  38. Jin W, Fukushima T, Niki M, Kosaka A, Ishii N, Aida T (2005) Proc Natl Acad Sci USA 102:10801

    CAS  Google Scholar 

  39. Gallivan JP, Schuster GB (1995) J Org Chem 60:2423

    CAS  Google Scholar 

  40. Nuckolls C, Katz TJ, Castellanos L (1996) J Am Chem Soc 118:3767

    CAS  Google Scholar 

  41. Lovinger AJ, Nuckolls C, Katz TJ (1998) J Am Chem Soc 120:264

    CAS  Google Scholar 

  42. Nuckolls C, Katz TJ, Katz G, Collings PJ, Castellanos L (1999) J Am Chem Soc 121:79

    CAS  Google Scholar 

  43. Mariani P, Mazabard C, Garbesi A, Spada GP (1989) J Am Chem Soc 111:6369

    CAS  Google Scholar 

  44. Bonazzi S, Capobianco M, De Morais MM, Garbesi A, Gottarelli G, Mariani P, Ponzi Bossi MG, Spada GP, Tondelli L (1991) J Am Chem Soc 113:5809

    CAS  Google Scholar 

  45. Gottarelli G, Spada GP (2004) Chem Rec 4:39

    CAS  Google Scholar 

  46. Andrisano V, Gottarelli G, Masiero S, Heijne EH, Pieraccini S, Spada GP (1999) Angew Chem Int Ed 38:2386

    CAS  Google Scholar 

  47. Ciuchi F, Di Nicola G, Franz H, Gottarelli G, Mariani P, Ponzi Bossi MG, Spada GP (1994) J Am Chem Soc 116:7064

    CAS  Google Scholar 

  48. Gottarelli G, Mezzina E, Spada GP, Carsughi F, Di Nicola G, Mariani P, Sabatucci A, Bonazzi S (1996) Helv Chim Acta 79:220

    CAS  Google Scholar 

  49. Kamikawa Y, Nishii M, Kato T (2004) Chem Eur J 10:5942

    CAS  Google Scholar 

  50. Sijbesma RP, Meijer EW (2003) Chem Commun 5

    Google Scholar 

  51. Jeukens CRLPN, Jonkheijm P, Wijnen FJP, Gielen JC, Christianen PCM, Schenning APHJ, Meijer EW, Maan JC (2005) J Am Chem Soc 127:8280

    CAS  Google Scholar 

  52. Hoeben FJM, Herz LM, Daniel C, Jonkheijm P, Schenning APHJ, Silva C, Meskers SCJ, Beljonne D, Phillips RT, Friend RH, Meijer EW (2004) Angew Chem Int Ed 43:1976

    CAS  Google Scholar 

  53. Jonkheijm P, Hoeben FJM, Kleppinger R, van Herrikhuyzen J, Schenning APHJ, Meijer EW (2003) J Am Chem Soc 125:15941

    CAS  Google Scholar 

  54. Schenning APHJ, Jonkheijm P, Peeters E, Meijer EW (2001) J Am Chem Soc 123:409

    CAS  Google Scholar 

  55. Wurthner F, Chen ZJ, Hoeben FJM, Osswald P, You CC, Jonkheijm P, von Herrikhuyzen J, Schenning APHJ, van der Schoot PPAM, Meijer EW, Beckers EHA, Meskers SCJ, Janssen RAJ (2004) J Am Chem Soc 126:10611

    Google Scholar 

  56. Schenning APHJ, von Herrikhuyzen J, Jonkheijm P, Chen Z, Wurthner F, Meijer EW (2002) J Am Chem Soc 124:10252

    CAS  Google Scholar 

  57. Feringa BL, van Delden RA (1999) Angew Chem Int Ed 38:3419

    CAS  Google Scholar 

  58. Green MM, Park JW, Sato T, Teramoto A, Lifson S, Selinger RLB, Selinger JV (1999) Angew Chem Int Ed 38:3139

    CAS  Google Scholar 

  59. Soai K, Shibata T, Sato I (2000) Acc Chem Res 33:382

    CAS  Google Scholar 

  60. Noyori R (2002) Angew Chem Int Ed 41:2008

    CAS  Google Scholar 

  61. Green MM, Reidy MP, Johnson RJ, Darling G, Oleary DJ, Willson G (1989) J Am Chem Soc 111:6452

    Google Scholar 

  62. Jha SK, Cheon KS, Green MM, Selinger JV (1999) J Am Chem Soc 121:1665

    CAS  Google Scholar 

  63. Green MM, Garetz BA, Munoz B, Chang HP, Hoke S, Cooks RG (1995) J Am Chem Soc 117:4181

    CAS  Google Scholar 

  64. Hirschberg JHKK, Brunsveld L, Ramzi A, Vekemans JAJM, Sijbesma RP, Meijer EW (2000) Nature 407:167

    CAS  Google Scholar 

  65. Hirschberg JHKK, Koevoets RA, Sijbesma RP, Meijer EW (2003) Chem Eur J 9:4222

    CAS  Google Scholar 

  66. Brunsveld L, Vekemans JAJM, Hirschberg JHKK, Sijbesma RP, Meijer EW (2002) Proc Natl Acad Sci USA 99:4977

    CAS  Google Scholar 

  67. Palmans ARA, Vekemans JAJM, Havinga EE, Meijer EW (1997) Angew Chem Int Ed Engl 36:2648

    CAS  Google Scholar 

  68. Brunsveld L, Lohmeijer BGG, Vekemans JAJM, Meijer EW (2000) Chem Commun 2305

    Google Scholar 

  69. Brunsveld L, Zhang H, Glasbeek M, Vekemans JAJM, Meijer EW (2000) J Am Chem Soc 122:6175

    CAS  Google Scholar 

  70. van Gorp JJ, Vekemans JAJM, Meijer EW (2002) J Am Chem Soc 124:14759

    Google Scholar 

  71. Brunsfeld L, Lohmeijer BGG, Vekemans JAJM, Meijer EW (2001) J Inclusion Phenom 41:61

    CAS  Google Scholar 

  72. van Gestel J, Palmans ARA, Titulaer B, Vekemans JAJM, Meijer EW (2005) J Am Chem Soc 127:5490

    Google Scholar 

  73. Brunsveld L, Schenning APHJ, Broeren MAC, Janssen HM, Vekemans JAJM, Meijer EW (2000) Chem Lett 292

    Google Scholar 

  74. Lightfoot MP, Mair FS, Pritchard RG, Warren JE (1999) Chem Commun 1945

    Google Scholar 

  75. Wilson AJ, Masuda M, Sijbesma RP, Meijer EW (2005) Angew Chem Int Ed 44:2275

    CAS  Google Scholar 

  76. de Jong JJD, Lucas LN, Kellogg RM, van Esch JH, Feringa BL (2004) Science 304:278

    Google Scholar 

  77. de Jong JJD, Tiemersma-Wegman TD, van Esch JH, Feringa BL (2005) J Am Chem Soc 127:13804

    Google Scholar 

  78. Fenniri H, Deng BL, Ribbe AE (2002) J Am Chem Soc 124:11064

    CAS  Google Scholar 

  79. Fenniri H, Deng BL, Ribbe AE, Hallenga K, Jacob J, Thiyagarajan P (2002) Proc Natl Acad Sci USA 99:6487

    CAS  Google Scholar 

  80. Onouchi H, Maeda K, Yashima E (2001) J Am Chem Soc 123:7441

    CAS  Google Scholar 

  81. Onouchi H, Kashiwagi D, Hayashi K, Maeda K, Yashima E (2004) Macromolecules 37:5495

    CAS  Google Scholar 

  82. Yashima E, Maeda Y, Okamoto Y (1996) Chem Lett 955

    Google Scholar 

  83. Yashima E, Maeda Y, Matsushima T, Okamato Y (1997) Chirality 9:593

    CAS  Google Scholar 

  84. Maeda K, Okada S, Yashima E, Okamoto Y (2001) J Polym Sci, Part A: Polym Chem 39:3180

    CAS  Google Scholar 

  85. Yashima E, Nimura T, Matsushima T, Okamoto Y (1996) J Am Chem Soc 118:9800

    CAS  Google Scholar 

  86. Kawamura H, Maeda K, Okamoto Y, Yashima E (2001) Chem Lett 58

    Google Scholar 

  87. Morino K, Watase N, Maeda K, Yashima E (2004) Chem Eur J 10:4703

    CAS  Google Scholar 

  88. Nonokawa R, Yashima E (2003) J Am Chem Soc 125:1278

    CAS  Google Scholar 

  89. Nonokawa R, Oobo M, Yashima E (2003) Macromolecules 36:6599

    CAS  Google Scholar 

  90. Nonokawa R, Yashima E (2003) J Polym Sci, Part A: Polym Chem 41:1004

    CAS  Google Scholar 

  91. Sakurai S, Kuroyanagi K, Nonokawa R, Yashima E (2004) J Polym Sci, Part A: Polym Chem 42:5838

    CAS  Google Scholar 

  92. Manning GS (1979) Acc Chem Res 12:443

    CAS  Google Scholar 

  93. Saito MA, Maeda K, Onouchi H, Yashima E (2000) Macromolecules 33:4616

    CAS  Google Scholar 

  94. Nagai K, Maeda K, Takeyama Y, Sakajiri K, Yashima E (2005) Macromolecules 38:5444

    CAS  Google Scholar 

  95. Yashima E, Goto H, Okamoto Y (1998) Polym J 30:69

    CAS  Google Scholar 

  96. Maeda K, Goto H, Yashima E (2001) Macromolecules 34:1160

    CAS  Google Scholar 

  97. Tabei J, Nomura R, Sanda F, Masuda T (2003) Macromolecules 36:8603

    CAS  Google Scholar 

  98. Ishikawa M, Maeda K, Yashima E (2002) J Am Chem Soc 124:7448

    CAS  Google Scholar 

  99. Yashima E, Maeda K, Yamanaka T (2000) J Am Chem Soc 122:7813

    CAS  Google Scholar 

  100. Schlitzer DS, Novak BM (1998) J Am Chem Soc 120:2196

    CAS  Google Scholar 

  101. Maeda K, Yamamoto N, Okamoto Y (1998) Macromolecules 31:5924

    CAS  Google Scholar 

  102. Sakai R, Satoh T, Kakuchi R, Kaga H, Kakuchi T (2003) Macromolecules 36:3709

    CAS  Google Scholar 

  103. Sakai R, Satoh T, Kakuchi R, Kaga H, Kakuchi T (2004) Macromolecules 37:3996

    CAS  Google Scholar 

  104. Green MM, Khatri C, Peterson NC (1993) J Am Chem Soc 115:4941

    CAS  Google Scholar 

  105. Dellaportas P, Jones RG, Holder SJ (2002) Macromol Rapid Commun 23:99

    CAS  Google Scholar 

  106. Majidi MR, Kane-Maguire LAP, Wallace GG (1995) Polymer 36:3597

    CAS  Google Scholar 

  107. Arnt L, Tew GN (2004) Macromolecules 37:1283

    CAS  Google Scholar 

  108. Nakashima H, Koe JR, Torimitsu K, Fujiki M (2001) J Am Chem Soc 123:4847

    CAS  Google Scholar 

  109. Inai Y, Tagawa K, Takasu A, Hirabayashi T, Oshikawa T, Yamashita M (2000) J Am Chem Soc 122:11731

    CAS  Google Scholar 

  110. Inai Y, Ousaka N, Okabe T (2003) J Am Chem Soc 125:8151

    CAS  Google Scholar 

  111. Okamoto Y, Matsuda M, Nakano T, Yashima E (1993) Polym J 25:391

    CAS  Google Scholar 

  112. Okamoto Y, Matsuda M, Nakano T, Yashima E (1994) J Polym Sci, Part A: Polym Chem 32:309

    CAS  Google Scholar 

  113. Maeda K, Matsuda M, Nakano T, Okamoto Y (1995) Polym J 27:141

    CAS  Google Scholar 

  114. Obata K, Kabuto C, Kira M (1997) J Am Chem Soc 119:11345

    CAS  Google Scholar 

  115. Ikeda C, Yoon ZS, Park M, Inoue H, Kim D, Osuka A (2005) J Am Chem Soc 127:534

    CAS  Google Scholar 

  116. Gellman SH (1998) Acc Chem Res 31:173

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  118. Prince RB, Moore JS, Brunsveld L, Meijer EW (2001) Chem Eur J 7:4150

    CAS  Google Scholar 

  119. Brunsveld L, Meijer EW, Prince RB, Moore JS (2001) J Am Chem Soc 123:7978

    CAS  Google Scholar 

  120. Inouye M, Waki M, Abe H (2004) J Am Chem Soc 126:2022

    CAS  Google Scholar 

  121. Maurizot V, Dolain C, Huc I (2005) Eur J Org Chem 1293

    Google Scholar 

  122. Berl V, Huc I, Khoury RG, Krische MJ, Lehn JM (2000) Nature 407:720

    CAS  Google Scholar 

  123. Maeda K, Morino K, Yashima E (2003) Macromol Symp 201:135

    CAS  Google Scholar 

  124. Yashima E, Maeda Y, Okamoto Y (1998) J Am Chem Soc 120:8895

    CAS  Google Scholar 

  125. Yashima E, Maeda K, Sato O (2001) J Am Chem Soc 123:8159

    CAS  Google Scholar 

  126. Morino K, Maeda K, Yashima E (2003) Macromolecules 36:1480

    CAS  Google Scholar 

  127. Yashima E, Maeda K, Okamoto Y (1999) Nature 399:449

    CAS  Google Scholar 

  128. Maeda K, Morino K, Okamoto Y, Sato T, Yashima E (2004) J Am Chem Soc 126:4329

    CAS  Google Scholar 

  129. Miyagawa T, Furuko A, Maeda K, Katagiri H, Furusho Y, Yashima E (2005) J Am Chem Soc 127:5018

    CAS  Google Scholar 

  130. Maeda K, Matsushita Y, Ezaka M, Yashima E (2005) Chem Commun 4152

    Google Scholar 

  131. Furusho Y, Kimura T, Mizuno Y, Aida T (1997) J Am Chem Soc 119:5267

    CAS  Google Scholar 

  132. Bellacchio E, Lauceri R, Gurrieri S, Scolaro LM, Romeo A, Purrello R (1998) J Am Chem Soc 120:12353

    CAS  Google Scholar 

  133. Sugasaki A, Ikeda M, Takeuchi M, Robertson A, Shinkai S (1999) J Chem Soc, Perkin Trans 1 3259

    Google Scholar 

  134. Rivera JM, Craig SL, Martin T, Rebek J Jr (2000) Angew Chem Int Ed 39:2130

    CAS  Google Scholar 

  135. Prins LJ, De Jong F, Timmerman P, Reinhoudt DN (2000) Nature 408:181

    CAS  Google Scholar 

  136. Kubo Y, Ohno T, Yamanaka J, Tokita S, Iida T, Ishimaru Y (2001) J Am Chem Soc 123:12700

    CAS  Google Scholar 

  137. Ishi-i T, Crego-Calama M, Timmerman P, Reinhoudt DN, Shinkai S (2002) J Am Chem Soc 124:14631

    CAS  Google Scholar 

  138. Prins LJ, Verhage JJ, de Jong F, Timmerman P, Reinhoudt DN (2002) Chem Eur J 8:2302

    CAS  Google Scholar 

  139. Purrello R (2003) Nat Mater 2:216

    CAS  Google Scholar 

  140. Ziegler M, Davis AV, Johnson DW, Raymond KN (2003) Angew Chem Int Ed 42:665

    CAS  Google Scholar 

  141. Lauceri R, Raudino A, Scolaro LM, Micali N, Purrello R (2002) J Am Chem Soc 124:894

    CAS  Google Scholar 

  142. Lauceri R, Purrello R (2005) Supramol Chem 17:61

    CAS  Google Scholar 

  143. Onouchi H, Miyagawa T, Furuko A, Maeda K, Yashima E (2005) J Am Chem Soc 127:2960

    CAS  Google Scholar 

  144. Ishikawa M, Maeda K, Mitsutsuji Y, Yashima E (2004) J Am Chem Soc 126:732

    CAS  Google Scholar 

  145. Goto H, Zhang HQ, Yashima E (2003) J Am Chem Soc 125:2516

    CAS  Google Scholar 

  146. Morino K, Oobo M, Yashima E (2005) Macromolecules 38:3461

    CAS  Google Scholar 

  147. Maeda K, Hatanaka K, Yashima E (2004) Mendeleev Commun 231

    Google Scholar 

  148. Proni G, Spada GP (2001) Enantiomer 6:171

    CAS  Google Scholar 

  149. Huck NPM, Jager WF, deLange B, Feringa BL (1996) Science 273:1686

    CAS  Google Scholar 

  150. Green MM, Zanella S, Gu H, Sato T, Gottarelli G, Jha SK, Spada GP, Schoevaars AM, Feringa B, Teramoto A (1998) J Am Chem Soc 120:9810

    CAS  Google Scholar 

  151. Maeda K, Takeyama Y, Sakajiri K, Yashima E (2004) J Am Chem Soc 126:16284

    CAS  Google Scholar 

  152. Lupas A (1996) Trends Biochem Sci 21:375

    CAS  Google Scholar 

  153. Burkhard P, Stetefeld J, Strelkov SV (2001) Trends Cell Biol 11:82

    CAS  Google Scholar 

  154. Maeda K, Ishikawa M, Yashima E (2004) J Am Chem Soc 126:15161

    CAS  Google Scholar 

  155. Nilsson KPR, Rydberg J, Baltzer L, Inganäs O (2004) Proc Natl Acad Sci USA 101:11197

    CAS  Google Scholar 

  156. Nilsson KPR, Rydberg J, Baltzer L, Inganäs O (2003) Proc Natl Acad Sci USA 100:10170

    CAS  Google Scholar 

  157. Nilsson KPR, Inganäs O (2003) Nat Mater 2:419

    CAS  Google Scholar 

  158. Cornelissen JJLM, Fischer M, Sommerdijk NAJM, Nolte RJM (1998) Science 280:1427

    CAS  Google Scholar 

  159. Saxena A, Guo GQ, Fujiki M, Yang YG, Ohira A, Okoshi K, Naito M (2004) Macromolecules 37:3081

    CAS  Google Scholar 

  160. Ichimura K (2000) Chem Rev 100:1847

    CAS  Google Scholar 

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Correspondence to Eiji Yashima .

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Mercedes Crego-Calama David N. Reinhoudt

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Maeda, K., Yashima, E. Dynamic Helical Structures: Detection and Amplification of Chirality. In: Crego-Calama, M., Reinhoudt, D.N. (eds) Supramolecular Chirality. Topics in Current Chemistry, vol 265. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_035

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