Amplification of Chirality by Supramolecular Polymerization of Pyrene Oligomers†
Alina L. Nussbaumer
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31-631-8057
Search for more papers by this authorDaniel Studer
Institute of Anatomy, University of Bern, Baltzerstrasse 2, 3000 Bern 9 (Switzerland)
Search for more papers by this authorVladimir L. Malinovskii
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31-631-8057
Search for more papers by this authorCorresponding Author
Robert Häner
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31-631-8057
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31-631-8057Search for more papers by this authorAlina L. Nussbaumer
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31-631-8057
Search for more papers by this authorDaniel Studer
Institute of Anatomy, University of Bern, Baltzerstrasse 2, 3000 Bern 9 (Switzerland)
Search for more papers by this authorVladimir L. Malinovskii
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31-631-8057
Search for more papers by this authorCorresponding Author
Robert Häner
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31-631-8057
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31-631-8057Search for more papers by this authorFinancial support by the Swiss National Foundation (grant 200020-132581) is gratefully acknowledged. The authors thank Prof. E. Castiglioni (Dipartimento di Scienze Biomediche e Biotecnologie, Università di Brescia, 25123 Brescia, Italy) for help with LD experiments.
Graphical Abstract
Achirale Pyrenoligomere α zeigen eine bemerkenswerte Chiralitätsverstärkung (siehe Circulardichroismusspektren) in Gegenwart geringster Mengen eines chiralen Induktors χ. Spektroskopische und elektronenmikroskopische Daten stützen ein Modell, dem zufolge die Pyrenoligomere durch Stapelwechselwirkungen helicale supramolekulare Polymere bilden.
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References
- 1L. Brunsveld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071–4097.
- 2J. M. Lehn, Polym. Int. 2002, 51, 825–839.
- 3S. Mann, Nat. Mater. 2009, 8, 781–792.
- 4J. M. Lehn, Supramolecular Chemistry—Concepts and Perspectives, VCH, Weinheim, 1995.
10.1002/3527607439 Google Scholar
- 5G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312–1319.
- 6J. S. Lindsey, New J. Chem. 1991, 15, 153–180.
- 7V. Percec, M. Glodde, T. K. Bera, Y. Miura, I. Shiyanovskaya, K. D. Singer, V. S. K. Balagurusamy, P. A. Heiney, I. Schnell, A. Rapp, H. W. Spiess, S. D. Hudson, H. Duan, Nature 2002, 417, 384–387.
- 8H. J. Schneider, Angew. Chem. 2009, 121, 3982–4036;
10.1002/ange.200802947 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 3924–3977.
- 9D. Pijper, B. L. Feringa, Soft Matter 2008, 4, 1349–1372.
- 10A. W. Bosman, R. P. Sijbesma, E. W. Meijer, Mater. Today 2004, 7, 34–39.
- 11J. D. Badjic, A. Nelson, S. J. Cantrill, W. B. Turnbull, J. F. Stoddart, Acc. Chem. Res. 2005, 38, 723–732.
- 12J. E. Anthony, Chem. Rev. 2006, 106, 5028–5048.
- 13E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. 2007, 119, 72–196; Angew. Chem. Int. Ed. 2007, 46, 72–191.
- 14L. C. Palmer, S. I. Stupp, Acc. Chem. Res. 2008, 41, 1674–1684.
- 15T. Rehm, C. Schmuck, Chem. Commun. 2008, 801–813.
- 16M. R. Wasielewski, Acc. Chem. Res. 2009, 42, 1910–1921.
- 17A. R. A. Palmans, J. A. J. M. Vekemans, E. E. Havinga, E. W. Meijer, Angew. Chem. 1997, 109, 2763–2765;
10.1002/ange.19971092328 Google ScholarAngew. Chem. Int. Ed. Engl. 1997, 36, 2648–2651.
- 18F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491–1546.
- 19T. F. A. de Greef, E. W. Meijer, Nature 2008, 453, 171–173.
- 20A. Lohr, F. Wurthner, Angew. Chem. 2008, 120, 1252–1256;
10.1002/ange.200704550 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 1232–1236.
- 21X. L. Feng, W. Pisula, L. J. Zhi, M. Takase, K. Mullen, Angew. Chem. 2008, 120, 1727–1730; Angew. Chem. Int. Ed. 2008, 47, 1703–1706.
- 22V. L. Malinovskii, D. Wenger, R. Häner, Chem. Soc. Rev. 2010, 39, 410–422.
- 23J. D. Hartgerink, E. R. Zubarev, S. I. Stupp, Curr. Opin. Solid State Mater. Sci. 2001, 5, 355–361.
- 24E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244–1287; Angew. Chem. Int. Ed. 2003, 42, 1210–1250.
- 25K. C. Hannah, B. A. Armitage, Acc. Chem. Res. 2004, 37, 845–853.
- 26P. G. A. Janssen, A. Ruiz-Carretero, D. Gonzalez-Rodriguez, E. W. Meijer, A. P. H. J. Schenning, Angew. Chem. 2009, 121, 8247–8250;
10.1002/ange.200903507 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 8103–8106.
- 27P. G. A. Janssen, S. Jabbari-Farouji, M. Surin, X. Vila, J. C. Gielen, T. F. A. de Greef, M. R. J. Vos, P. H. H. Bomans, N. A. J. M. Sommerdijk, P. C. M. Christianen, P. Leclere, R. Lazzaroni, P. van der Schoot, E. W. Meijer, A. P. H. J. Schenning, J. Am. Chem. Soc. 2009, 131, 1222–1231.
- 28R. Iwaura, M. Ohnishi-Kameyama, T. Iizawa, Chem. Eur. J. 2009, 15, 3729–3735.
- 29H. Kitagishi, K. Oohora, T. Hayashi, Biopolymers 2009, 91, 194–200.
- 30S. H. Gellman, Acc. Chem. Res. 1998, 31, 173–180.
- 31D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893–4011.
- 32I. Huc, Eur. J. Org. Chem. 2004, 17–29.
- 33E. Yashima, K. Maeda in Foldamers—Structure, Properties, and Applications (Eds.: ), Wiley-VCH, Weinheim, 2007, pp. 331–366.
- 34Y. Wang, F. Li, Y. M. Han, F. Y. Wang, H. Jiang, Chem. Eur. J. 2009, 15, 9424–9433.
- 35D. Haldar, C. Schmuck, Chem. Soc. Rev. 2009, 38, 363–371.
- 36S. M. Langenegger, R. Häner, Chem. Commun. 2004, 2792–2793.
- 37S. M. Langenegger, R. Häner, ChemBioChem 2005, 6, 848–851.
- 38S. M. Langenegger, R. Häner, Bioorg. Med. Chem. Lett. 2006, 16, 5062–5065.
- 39I. Trkulja, R. Häner, Bioconjugate Chem. 2007, 18, 289–292.
- 40I. Trkulja, R. Häner, J. Am. Chem. Soc. 2007, 129, 7982–7989.
- 41F. Samain, V. L. Malinovskii, S. M. Langenegger, R. Häner, Bioorg. Med. Chem. 2008, 16, 27–33.
- 42M. H. Caruthers, Science 1985, 230, 281–285.
- 43V. L. Malinovskii, F. Samain, R. Häner, Angew. Chem. 2007, 119, 4548–4551;
10.1002/ange.200700891 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 4464–4467.
- 44R. Häner, F. Samain, V. L. Malinovskii, Chem. Eur. J. 2009, 15, 5701–5708.
- 45V. A. Galievsky, V. L. Malinovskii, A. S. Stasheuski, F. Samain, K. A. Zachariasse, R. Häner, V. S. Chirvony, Photochem. Photobiol. Sci. 2009, 8, 1448–1454.
- 46R. Häner, F. Garo, D. Wenger, V. L. Malinovskii, J. Am. Chem. Soc. 2010, 132, 7466–7471.
- 47F. M. Winnik, Chem. Rev. 1993, 93, 587–614.
- 48K. A. Zachariasse, W. Kuhnle, A. Weller, Chem. Phys. Lett. 1978, 59, 375–380.
- 49K. Zachariasse, W. Kuhnle, Z. Phys. Chem. 1976, 101, 267–276.
- 50S. Werder, V. L. Malinovskii, R. Häner, Org. Lett. 2008, 10, 2011–2014.
- 51H. Bittermann, D. Siegemund, V. L. Malinovskii, R. Häner, J. Am. Chem. Soc. 2008, 130, 15285–15287.
- 52C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651–669.
- 53M. M. Green, N. C. Peterson, T. Sato, A. Teramoto, R. Cook, S. Lifson, Science 1995, 268, 1860–1866.
- 54M. M. Green, J. W. Park, T. Sato, A. Teramoto, S. Lifson, R. L. B. Selinger, J. V. Selinger, Angew. Chem. 1999, 111, 3328–3345;
10.1002/(SICI)1521-3757(19991102)111:21<3328::AID-ANGE3328>3.0.CO;2-Z Web of Science® Google ScholarAngew. Chem. Int. Ed. 1999, 38, 3138–3154.10.1002/(SICI)1521-3773(19991102)38:21<3138::AID-ANIE3138>3.0.CO;2-C CAS PubMed Web of Science® Google Scholar
- 55A. R. A. Palmans, E. W. Meijer, Angew. Chem. 2007, 119, 9106–9126;
10.1002/ange.200701285 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 8948–8968.
- 56K. Maeda, E. Yashima, Top. Curr. Chem. 2006, 265, 47–88.
- 57T. E. Kaiser, V. Stepanenko, F. Würthner, J. Am. Chem. Soc. 2009, 131, 6719–6732.
- 58P. Rivera-Fuentes, J. L. Alonso-Gomez, A. G. Petrovic, F. Santoro, N. Harada, N. Berova, F. Diederich, Angew. Chem. 2010, 122, 2296–2300;
10.1002/ange.200906191 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 2247–2250.
- 59T. F. A. de Greef, M. M. J. Smulders, M. Wolffs, A. P. H. J. Schenning, R. P. Sijbesma, E. W. Meijer, Chem. Rev. 2009, 109, 5687–5754.
- 60M. M. Green, K. S. Cheon, S. Y. Yang, J. W. Park, S. Swansburg, W. H. Liu, Acc. Chem. Res. 2001, 34, 672–680.
- 61M. M. Green, M. P. Reidy, R. J. Johnson, G. Darling, D. J. Oleary, G. Willson, J. Am. Chem. Soc. 1989, 111, 6452–6454.
- 62E. Yashima, K. Maeda, H. Iida, Y. Furusho, K. Nagai, Chem. Rev. 2009, 109, 6102–6211.
- 63F. Totsingan, V. Jain, W. C. Bracken, A. Faccini, T. Tedeschi, R. Marchelli, R. Corradini, N. R. Kallenbach, M. M. Green, Macromolecules 2010, 43, 2692–2703.
- 64N. Berova, K. Nakanishi, R. W. Woody, Circular Dichroism—Principles and Applications, 2nd ed., Wiley-VCH, New York, 2000.
- 65N. Berova, L. Di Bari, G. Pescitelli, Chem. Soc. Rev. 2007, 36, 914–931.
- 66G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1–73.
- 67M. M. J. Smulders, A. P. H. J. Schenning, E. W. Meijer, J. Am. Chem. Soc. 2008, 130, 606–611.
- 68T. Ishi-i, R. Kuwahara, A. Takata, Y. Jeong, K. Sakurai, S. Mataka, Chem. Eur. J. 2006, 12, 763–776.
- 69M. M. J. Smulders, M. M. L. Nieuwenhuizen, T. F. A. de Greef, P. van der Schoot, A. P. H. J. Schenning, E. W. Meijer, Chem. Eur. J. 2010, 16, 362–367.
- 70M. M. Green in Circular Dichroism—Principles and Applications (Eds.: ), Wiley-VCH, Hoboken, NJ, 2000, pp. 491–520.
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